The Most Romantic Date Ideas For Valentine’s Day in Chicago in 2024

What to do if you’re looking for Romantic Date Ideas For Valentine’s Day in Chicago. You’ll find everything from exciting date ideas to the most romantic date ideas for Valentine’s Day in Chicago.

Chicago has everything you’re searching for, whether you’re a native seeking new date ideas or a visitor having a romantic getaway.

The ideal location to win over that particular someone in your life is a city with a vibrant culture, beautiful historic buildings, and exciting adventures. Chicago has interesting sites to see in any season, so you won’t run out of things to do even if the weather wrecks your plans.

Thanks to the abundance of attractions, various cuisines to try, comfortable surroundings, and exciting activities, your date night will be a romantic and enthralling experience.

In Chicagoland, treat your date to a fun-filled day of exercise or a classic dinner and drink date. These 69 Chicago date ideas can help you maximise your time together.

69 Romantic Date Night Ideas in Chicago

Spread Out A Picnic In The Park

A fine assortment of wine and gourmet snacks wrapped inside a basket may dress up the custom of bringing meals to attractive locations.

In one of Chicago’s numerous parks, sprawl with your significant other and enjoy your favourite spread while watching the sunset behind the city’s famous skyline.

For instance, the historic Humboldt Park has lagoons, boathouses, an inland beach, and more. What was once a prairie community that developed into a hub for leisure activities is now a charming location for spreading out your picnic blanket.

While chatting with your special someone, you can order caviar and other treats from the nearby Heritage Restaurant and Caviar Bar.

Burnham Park also has Promontory Point, which provides a breathtaking skyline perspective. Beginning with this artificial peninsula, architect Daniel H.

Burnham envisioned a vast park with islands, a boat harbour, beaches, play spaces, and other features. Even though Burnham’s vision for the park was never fully realized, the location is a lovely spot to take in Chicago, and Lake Michigan is also a splendour.

Both places are perfect for a romantic day out, but to make the picnic-in-the-park experience even more unique, surprise your significant other with a stunning bouquet.

Dinner And A Movie — With A Twist

Chicago’s distinctive alternatives spice up the standard date option of dinner and a movie. Bring a bunch of garden roses to your date’s door to begin the evening.

Try Music Box Theatre if you and your date want to explore independent films or if box office smashes are not your thing. When it first debuted in 1929, the theatre was viewed as a scaled-down imitation of Chicago’s thriving movie palaces.

These days, this theatre draws sizable numbers of people because of its unusual film selection. It frequently screens international movies, and if you can attend it on a special night, you can see the world premiere of an independent film. To sample the most excellent steak in Argentina, stop by Tango Sur first.

At AMC Dine-in Block 37, you can watch a movie while eating. You and your significant other may choose what to eat from your seat.

Your food options, including sushi, flatbread, and more, are served straight to you so you can watch the big screen comfortably. You are no longer confined to buttery popcorn.

Take A Stroll On The Pier

The iconic Chicago Navy Pier is a buzzing entertainment hub and gastronomic destination. The pier also offers culinary excursions, allowing you and your date to explore a variety of eateries without being limited to just one. If you’re craving pizza, treat yourself to Giordano’s, a favourite in Chicago for its deep dish.

With your date, you may have fun at the pier with games and rides. The extensive list of attractions offers an endless itinerary. Ride the coasters or use the remote-controlled boats to satisfy your competitive side.

To cap off your evening at the pier, draw your special someone close on the renowned Centennial Wheel. The sparkling city lights from the top of the Ferris wheel provide the ideal ambience.

Take In The Music At A Jazz Lounge

Jazz’s impromptu and mellow melodies offer a seductive environment for dates. The jazz clubs in Chicago transport you back to the early 1900s when rhythmic music emerged. You may both wear the part to make your jazzy date night even more special.

Live music may be heard at Green Mill Cocktail Lounge, which has décor similar to Clark Monroe’s Uptown House in Harlem. Grab a classic drink with your date and enjoy a relaxing night of talk and music.

A live magazine act called “Paper Machete” is also frequently presented at this club. Seating cannot be booked, so check the schedule of performances for the most well-known artists and arrive early to get a place.

Andy’s Jazz Club and Restaurant in the River North neighbourhood were originally popular among journalists and other media employees. Society embraced jazz around the middle of the 1970s.

Laugh Along At A Comedy Night

One of the finest ways to start a date night is with laughter, which is also the best medicine. Attend a comedy club to start your date on a lighthearted and romantic note; Chicago offers several great spots to laugh.

Second City is a renowned comedy venue and a training ground for comics. It has hosted several well-known comedians, including Steve Carell and Tina Fey.

You may see improvised performances, comedy, and musical numbers. A branch of Second City called Up Comedy Club presents stand-up comedy performances.

Another venue for stand-up comedy is The Comedy Bar, which has a brewery and a restaurant. As the comedians create a fun backdrop for your night out, enjoy comfort cuisine with your significant other.

Zanies brings in top-tier performers every night for their nonstop jokes and belly-laugh-inducing antics. This comedy club has been successful for 40 years, and if you want to learn how to tell jokes well, it also provides comedy lessons.

Take In The Views At The Conservatory

Although the city’s skyline, architecture, and brilliant lights are all stunning, green regions are also special.

The glass-enclosed Garfield Park Conservatory has luxuriant indoor and outdoor gardens that close in the winter. However, you can bring your date to this verdant retreat at any time of year to unwind.

The enormous floral refuge, the Garfield Park Conservatory, has eight indoor sections. Explore the fern and palm chambers and the water lily pond.

The public dining area and event space in Horticulture Hall allow an even closer examination of the plant life.

Before the date, send your date some lovely flowers or a blossoming plant to hint about your location.

Visit The Zoo

If you both appreciate nature, visit the Lincoln Park Zoo with your date. Since you don’t see giraffes or monkeys daily, the range of unusual creatures encourages lively discourse. Take advantage of the opportunity to enjoy the variety of the animal kingdom with your favourite pet.

This establishment is the fourth-oldest zoo in the United States, operating for over 150 years. The Lincoln Park Zoo is accessible to everyone year-round, thanks mainly to the proceeds from its gift shops and fundraising efforts.

Browse An Art Gallery Arm-in-arm

Consider taking your significant other on a date when you explore Chicago’s art museums or galleries and talk about the artworks you see. Chicago has many venues to choose from because it has an abundance of art collections.

The unique works of art throughout Chicago’s Museum of Contemporary Art may be appreciated without much historical understanding.

This museum’s architecture also showcases ground-breaking works of art by Josef Paul Kleihues. As you stroll through it, you and your date may admire the optical beauty created by his north staircase.

The Art Institute of Chicago features a wide range of civilizations, historical periods, and artistic genres for history enthusiasts.

You may enjoy several types of art together, including paintings, sculptures, textiles, and photography.

Depending on your mood and interests, you and your date may enjoy either because Chicago’s art galleries showcase upcoming artists, and its museums honour former artists.

As you tour the galleries with your date, ask them about their preferences to learn more about them and the art world.

Meet For Drinks

Visit the chicest bars and breweries Chicago offers with your sweetheart. Try different wines or visit themed pubs with entertaining settings.

Many old bars in Chicago can keep you entertained with fantastic music and a speakeasy atmosphere.

The Violet Hour is a bar with a Wicker Park address that models its decor and libations after the years shortly before Prohibition began to restrict alcohol use in the country in 1920.

A single light bulb lights an often-changing mural at the entryway to this upscale location, creating a deliciously dramatic impression.

Candles, blue leather high-backed chairs, crystal chandeliers, and other elements create a beautiful ambience.

Another famous tavern that plays jazz and country music is The California Clipper.

This pub combines today’s music with its musical heritage from the 1930s. It still has a jukebox with current songs. The interior’s crimson tint will make any date attractive.

It’s a great idea to try something new on a date, and Chicago’s bars have many creative cocktails and unique surroundings.

Chicago’s many taprooms may satisfy every fancy, whether you want to sample the newest adult beverage creation or are mesmerized by the scenery.

The Aviary is a bar that focuses on inventive alcoholic cocktails that redefine the term “innovation.”

Whether your beverage arrives as a vapour-filled teapot or an orb in a glass, this experience will excite your special night.

The Signature Lounge is housed in a contemporary, tall building with a clear, mesmerizing view of the setting sun.

Watch the light grow golden while enjoying an Old Fashioned with your date. The view of the metropolis and skyscrapers at nightfall is as picturesque as a date in Chicago can be.

Sculpt A Masterpiece Together

Enrol in a pottery class with your significant other to experience new and personal ways to connect. This practical exercise will bring out your creative side.

Penguin Foot Pottery welcomes both beginner and more experienced clay students. This Logan Square facility offers several levels of hand development and wheel throwing for novices.

Although you and your companion might buy a series of lessons, drop-in sessions are also offered briefly.

For shorter, one-time classes, drop by during their designated drop-in hours; Penguin Foot does not require appointments.

Park West Ceramics is a different place to express yourself creatively. This Lincoln Park facility offers beginner workshops for lessons.

The student-to-instructor ratio in these courses is low; each participant will have created one piece of art at the program’s end.

Just remember that creating pottery is messy, so make sure your date is wearing clothes that can get filthy!

Climb The Willis Tower And Skydeck Ledge

Willis Tower, once known as the Sears Tower and rising 110 floors, is a striking structure. From the summit perspective, four states—Illinois, Indiana, Wisconsin, and Michigan—can be seen.

To give you and your date a burst of energy before climbing the tower—even if the elevator is one of the quickest functioning elevators in the world—visit a nearby coffee shop.

Before you set out for the tower, you can get a smooth dark roast from Mojo Coffee, a nearby New Zealand coffee roaster. Floriole is another café with a bakery that enjoys using organic food.

Visitors may go outside and enjoy a recognizable view of Chicago from the Skydeck, also known as the observation deck, close to the structure’s top. A glass viewing area on the Skydeck’s ledge gives the impression that you are hanging in midair.

The Chicago skyline may be seen in all its glory from there, directly beneath your feet! It’s an experience you and your date won’t soon forget.

Go On A Hike

With a few neighbouring state parks to explore, you and your companion will discover the ideal hiking site. Nature provides one of the most lovely and romantic dates in Chicago. Visit the Waterfall Glen Forest Preserve in DuPage County to spend some time in nature.

This serene outdoor retreat offers magnificent vistas, tranquil waterfalls, several paths, and picnic areas. If you enjoy the outdoors and don’t mind travelling a half-hour outside of the city, this spot is ideal for a great date.

Ice Skate Hand-in-hand

During the colder months, grab your ice skates and go to Maggie Daley Park in the heart of Chicago. This mercurial twisting rink provides fantastic city skyline views and maximum fun.

If you’re looking for things to do in Chicago at night, what could be more romantic than skating under the stunning Chicago night sky? Make sure you reserve in advance online!

Maggie Daley Park offers entertaining activities all year round, so if you’re planning a spring or summer date and the rink is closed for the season, have no fear! You’ll likely find something you like, whether mini-golf, tennis, the climbing wall, or a leisurely garden stroll.

Treat Your Sweet Tooth

What better way to spend a pleasant evening than with some delicious goodies? JoJo’s Shake Bar in River North offers loaded milkshakes, vintage cocktails, and other delectable sweets for your sweetest cravings.

This wacky milkshake establishment gives the typical ice cream date a distinctive twist. If you don’t want to stick with desserts, there are plenty of traditional bar selections, like onion rings and Buffalo wings.

Kayak On The River

Your list of romantic dates in Chicago should include a serene cruise down the Chicago River. While kayaking in the great outdoors is a timeless date idea, paddling amongst skyscrapers gives the activity a distinctively urban flavour.

You can reserve a kayak excursion with Wateriders that offers stunning city views. When you book your trip on the river, you’ll see Chicago from a different angle and create beautiful plans for a special date.

Hit The Lanes

Bowling is a pleasant and traditional date night activity, but Chicago gives it an intriguing twist. The best date night in Chicago is at Kings Dining & Entertainment in Lincoln Park, where you can take in a disco-like setting from the ’70s, tasty appetizers, and a friendly bowling battle.

Another fantastic place for a date is Waveland Bowl, which offers 40 bowling lanes, terrific rates, and delectable Chicago-style cuisine. With Waveland Bowl’s group rental options, you may reserve a lane to add extra couples or make it a double date.

Accent Your Date With Flowers

Bring your date a floral arrangement from Ode à la Rose to complement each of these outings and up the romance. You may choose the ideal bouquet for your significant other, whether a trademark bouquet or an anniversary arrangement for a special occasion.

A signature gift box delivered gives your floral selection a classy touch. Set the tone for your evening by providing your date flowers when you pick them up or sending a bouquet of roses to their office.

As an additional method to complete your date night ideas, add some rose petals for a romantic touch to your privacy settings. You may scatter these rose petals, available in pink, crimson, or white, on tables, the floor, and other surfaces to provide a charming appearance.

Stroll Through Millennium Park

Visit the renowned Millennium Park for one of Chicago’s top free date ideas. Explore the grounds, take in the fountains, and discover fantastic public art.

This area should be investigated if you’re searching for a place to stay in Chicago while you’re there.

It would be best if you took a picture in front of the famous Cloudgate sculpture, popularly referred to as the Bean. Share the image on social media to brag about your fantastic date in Chicago!

Numerous free events and concerts are held at Millennium Park annually. Every interest may be satisfied. This is a fantastic way to cut costs on your date without sacrificing pleasure!

Put this on your romantic Chicago agenda if you have two days there!

Dine at Alinea

Consider reserving at Alinea if you’re seeking one of Chicago’s best date night restaurants. At this premium restaurant, you’ll develop a fresh perspective on what food can be.

This award-winning restaurant will wow you with its inventive and contemporary cuisine, distinct to the palate and the eye.

Chef Grant Achatz’s cuisine has been awarded three Michelin stars because of its use of molecular gastronomy. Several dishes throughout your lunch will feature both great dining and exploration.

Be prepared to make a reservation far in advance to ensure a table. Although this is not an inexpensive dating night, serious foodies will find it worthwhile.

One of the most excellent spots to experience Chicago at night is undoubtedly here!

Take a Helicopter Tour

Consider taking a helicopter trip if you want the ideal adventurous date idea. This is a beautiful way to have an unforgettable time in Chicago.

As you soar overhead, you will be treated to breathtaking views of the recognizable skyline with its tall skyscrapers and ballparks. The size of the lake will also be visible to you.

To make the experience even more romantic, sign up for a sunset tour and take in the colourful sky. As night falls, the city’s lights will glisten.

One of the most romantic things to do for an anniversary or other special occasion in Chicago is this. There isn’t a more ideal date concept.

This is much more striking if you’re in Chicago during the fall.

Bike Along the Lake

Another inexpensive date idea is to ride a bike by the river in Chicago. Several bike-share stations around the city allow you to borrow a bike for a reasonable rate.

Grab your bikes and ride them to the Lakefront Trail. Incredible vistas of Lake Michigan and the city can be found on each side of this 18-mile paved cycling trail.

The path has many attractions. If you become weary of bicycling, you may stop at some parks, museums, and beaches.

After all that activity, foodies in Chicago may look forward to breakfast if hungry.

Watch Fireworks at Navy Pier

Another popular place to go on dates in Chicago is the Navy Pier. And one of the Midwest’s trendiest destinations.

The 3,300-foot-long pier has many entertaining things to fill a fantastic date night.

Visit the Centennial Wheel, look for some exciting statuary, or get something to drink at the Navy Pier Beer Garden. There are several restaurants and retail establishments.

There are fireworks displays every Wednesday and Saturday night from May through August. Kiss each other while the sky above you is illuminated. How love-inducing is that?

Watch the moon reflect on the lake to cap off your romantic evening in Chicago.

Explore the Lincoln Park Conservatory

The Lincoln Park Conservatory is the perfect date-night destination if you enjoy nature and want to save money. This free attraction is in a stunning late 1800s iron and glass structure.

Take your partner by the hand and stroll among the beautiful tropical vegetation. Since the inside is always open and lush, you may feel some warmth even during the bitter Chicago winters.

The grounds extend outside with fountains and statues. The lovely Alfred Caldwell Lily Pool is another feature you’ll adore. It’s a beautiful spot to explore and snap pictures.

Grab a Drink at the Darling

Go to the Darling for a more carefree and laid-back date. This stunning lounge in Fulton Market is furnished with dark hardwood, leather seats, chandeliers, and floor-to-ceiling bookcases.

As you drink cocktails in the cosy setting, you’ll feel like you’ve entered an ancient English house. Live music and various entertainers, including dancers and magicians, are frequently present.

The enormous Scrabble board mounted on the wall is a neat addition. While playing a game, you can enjoy the pleasant ambience.

Chicago has so many fantastic breweries that you should check out!

Take a Pottery Class

Consider taking up pottery if you want to pick up a new pastime with your date. This is a fantastic opportunity to be inventive while enjoying a fun date night.

If you don’t mind getting dirty, consider signing up for a class at Penguin Foot Pottery in Chicago. Beginners will enjoy learning the fundamentals using the materials offered.

If you are captivated after one lesson, you may practice your craft in a course that lasts a few weeks.

Then, you may adorn your house with your new pottery. The memories of the date will stay longer if you have something physical to show for your time together.

Don’t forget to check out Chicago’s many beautiful eateries!

Play Some Arcade Games

Bring your date to Headquarters Beercade if you want some entertaining competition. This is one of the finest things to do in Chicago for young-at-heart couples because it is both a bar and an arcade.

Here, you will have a blast with the classic pinball and arcade games. The menu has pizza, burgers, tacos, speciality fries, and a selection of beers on tap.

Come to one of the trivia evenings and put your pop culture knowledge to the test if you want even more games.

Admire Views At A Rooftop Bar

Several rooftop pubs are dotted across the city, perfect for a fun night in Chicago. Check out a different location every weekend for fresh, breathtaking skyline views from outdoor balconies.

Each bar has unique qualities. They feature a combination of adorable and modern designs, with moods that range from laid-back to party-like. You can locate a great bar to bring your date to, no matter what you seek.

ROOF on the Wit, I|O Urban Roofscape, and Cabra are some of Chicago’s most excellent rooftop bars. One of the most beautiful things for couples in Chicago is to sip beverages outside.

These are some of the top locations in Chicago to see holiday decorations.

Enjoy Happy Hour at the Chicago History Museum

Have you ever wanted to combine drinking with history? With several History Happy Hour events each year, the Chicago History Museum has you covered.

You get two drinks with your event ticket. Additional beverages and snacks are available at the bar.

This after-hours event will give you and your date a more intimate experience. You will have access to the museum when it is less busy and get a close-up view of the displays.

Try Playing Whirlyball For An Active Date Night In Chicago!

If Whirlyball is new to you, you’re in for a treat! This is a fantastic idea for a first or double date with friends.

A whirly ball is a novel game that combines basketball, lacrosse, and bumper cars. You will navigate the court in a bumper car moving at four mph while attempting to toss a Wiffle ball at a hanging target.

This is the date for you if you enjoy having a good time and being active! Because it’s so casual, you won’t be pressured to display your athletic prowess.

Additionally, bowling and laser tag are accessible here. Once you’ve finished playing, get a bite to eat in the restaurant or bar. After this, date evenings in Chicago will never be the same!

Go Ice Skating at Maggie Daley Park

Ice skating is the ideal option for a winter date night idea! You may test your skating prowess at the Maggie Daley Park Skating Ribbon.

On this ice ribbon, you may travel around and around while enjoying views of the buildings. Holding hands is the ideal solution if you feel wobbly on your skates.

Another skating rink in the area is the McCormick Tribune Ice Rink at Millennium Park, close to the Bean. This rink is more rectangular and conventional.

Each rink is accessible from November through March. Ice skating is one of the finest holiday activities in Chicago.

Sample Drinks at Koval Distiller For A Cool Date Night In Chicago

A visit to the Koval Distillery is one of the most excellent dates in Chicago. This location, which has a stunning tasting room, exudes romanticism.

The tasting area, decorated in the 1970s, features plush couches and wood accents. Order a flight of whisky, gin, or cocktails and unwind there. A terrace is also available when it’s pleasant outside.

Additionally, you may tour the distillery to see how the whisky is produced. Check out Koval’s cocktail lessons if you want further drink-related suggestions for a romantic night in Chicago.

Head To The Theater For Date Night In Chicago

If you want to watch a musical or a movie, Chicago has many large and small theatres. There are nearly 250 theatres in what is referred to as the “theatre capital of America.”

Of course, the Chicago Theatre is the most well-known theatre in the area. This elegant and historic theatre, owned by the Madison Square Garden Company, hosts Broadway musicals, concerts, and other events.

However, if you’re looking for less expensive tickets, there are several smaller theatres to attend. Visit the Black Ensemble Theater for presentations about Black life, history, and empowerment worthy of a dance.

Court Theater, which innovates on stage by adapting classics, earned the Regional Theatre Tony Award in 2022. You will see incredible performances regardless of the theatre you select.

If a movie showing appeals to you more than a live performance, purchase a ticket for the Music Box Theatre. During midnight showings, independent and international films, as well as cult classics, are shown here.

The popcorn at this theatre is famous for having actual butter on it. Yum! With this tried-and-true date night plan in Chicago, you can’t go wrong.

Packing List When Having A Date Night In Illinois

Here are some suggestions on how to pack efficiently for your Chicago date night if you’re looking.

A disguised travel bag is one of the most crucial items you should pack when visiting Chicago, Illinois. You should always secure your personal information. There are many identity thieves.

This lightweight, multicoloured, unisex hidden travel pouch blocks RFID technology. It is highly organized to provide you with comfort. To carry your ID securely, tuck it beneath your clothing close to your body.

These RFID sleeves are ideal if you already own a bag without RFID protection, like me.

Consider an external charging battery if you use your phone to take many images. I always travel with the same high-speed Anker phone charging battery.

I enjoy that it retains its charging capacity across numerous uses, allowing me to travel worry-free. Even if I forget to recharge it at night, it will still work the next day.

My daughter gave me this FugeTek selfie stick and tripod combo for my birthday. I adore it so much! It is straightforward to operate and composed of lightweight aluminium.

It is simple to use and offers Bluetooth connectivity for selfies, perfect for Instagram.

Chicago events you go to.

I’ve never been a big fan of packing cubes for trips until I tried them. I’m addicted now. When I pack for a vacation, I use these cubes to stay organized.

Your refillable water bottle should be brought along.

I always bring my Bobble filtration bottle on vacations from home. Its 18.5-ounce weight is ideal for excursions and fits comfortably in a backpack’s pocket.

Perhaps you are driving a long distance and have limited room in your car or bag for packing. Then, you’d benefit from this foldable, collapsible silicone water bottle set, which would not take up much space.

You should have a daypack or backpack to carry additional clothing, a phone, food, and water, regardless of the day or night.

This collapsible, water-resistant backpack is fantastic. And there are several hues available.

Finding romantic activities in Chicago for a memorable date night is so simple! There are several bars and eateries where you may find a quiet spot to talk.

Due to the abundance of parks and lakefront vistas, Chicago offers many free or low-cost date night activities, such as hiking, bicycling, and picnicking.

Plan a vacation to Chicago if you want to do something special for your anniversary. For couples seeking the trendiest things to do in Illinois, it is one of the top cities in the Midwest.

The Most Interesting Date Ideas in Chicago

It’s officially summer in Chicago, and we hope your romantic life is getting hotter! While there are many romantic restaurants in Chicago where you may wine and dine you’re SO, sometimes breaking the dating mould with something more unique is excellent.

This is true whether you’re navigating a flirtatious new affair or wanting to reignite flames in a long-term partnership. Are you looking for some inspiring love? Please allow us to assist you.

Here are some of our favourite suggestions for inventive dates in Chicago for romantic relationships, spiritual connections, and everything in between. They range from calm afternoons at the city’s top art galleries to exhilarating axe-throwing games.

Get dinner at Time Out Market Chicago.

Any stage of a relationship makes it challenging to decide where to dine, so why not streamline date night? Time Out Market Chicago can accommodate your needs if you want sushi and your companion prefers pizza.

There is cuisine for almost every taste, whether you’re in the mood for tacos, ramen, fried chicken, or ice cream, as some of the city’s top chefs operate 18 restaurants. Place a food order, have a drink, and let the conversation flow.

Glide around in a swan-shaped boat.

Swans are known to have lifelong relationships. Even if you aren’t looking to tie the knot, the graceful birds still make for attractive, romantic symbols, especially when they are in the shape of boats.

Swan boat tours on the Humboldt Park Lagoon are available from May through September for $30 per hour. After paddling, stroll to see the old boathouse’s Prairie-style architecture.

Pet some pups at the Montrose Dog Beach.

Why attend the Westminster Dog Show when you see endless dogs running around the beach for nothing? Dogs and their owners have their section of Montrose Beach that is walled off, but we bet you and your date could pet a few friendly dogs with the owners’ permission (and if all else fails, there’s no wrong in dog watching for a bit).

Cuddle up at The Point

Promontory Point, often known as The Point, is a man-made peninsula in Burnham Park’s Hyde Park section, ideal for a prolonged date.

Arrive in the afternoon, paddle around in the lake for a bit (the calmer south end is much better for swimming, FYI), then go over to the north end and take a seat on the rocky barrier to take in one of the most incredible views of Chicago’s skyline as the sun sets.

Stroll along the 16th Street Murals.

A dynamic and ever-evolving outdoor gallery of murals by well-known and up-and-coming painters may be seen on the walls of an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

As you cross 16th street, make an impression on your date by pointing out some of your favourite art pieces, whether you like vibrant works by renowned local artists like JC Rivera and Hebru Brantley or the contributions from global street artists like ROA and Sheryo.

Spot lions, tigers, and bears at Lincoln Park Zoo

There aren’t many places better for a first date than Lincoln Park Zoo since A) it’s free to visit and B) it’s packed to the gills with topics to discuss when conversation flags.

While exchanging getting-to-know-you pleasantries, point out pygmy hippos and polar bears; if things go well, you can always continue the night at a neighbouring pub.

Get lost inside the Garfield Park Conservatory.

Are you looking for an inexpensive date idea? Although reservations are required and gifts are appreciated, the Garfield Park Conservatory is free and open every day of the year.

You and your date may stroll around the conservatory’s 10 acres of outdoor gardens or explore the internal chambers stuffed to the gills with various plant species, such as palm palms, enormous succulents, and prehistoric ferns.

Tour Chicago Avenue’s best art galleries

Some of the city’s most significant and inventive galleries are located along Chicago Avenue between Ashland Avenue and Wood Street, making a reasonable and free walking art tour possible.

Head west after starting at the Matthew Rachman Gallery, which features modern art and stylish mid-century furniture.

You’ll see notable galleries such as DOCUMENT, Rhona Hoffman Gallery, Volume, and more along the road. Just be aware that many galleries now demand reservations before visitors.

See an indie movie at the Music Box.

You and your date could go to the cinema to see the newest blockbuster. Still, it would be more romantic to snuggle up in the Music Box’s historic 750-seat theatre, where you can see everything from international flicks to independent documentaries on the big screen.

If you truly want to demonstrate how much you care, ask for additional (genuine) butter on your bag of popcorn.

Have a beer by the river.

Do you want a drink with a view? There’s no need to spend money on costly drinks at a rooftop bar (unless you want to).

Visit Metropolitan Brewing instead for affordable German-style beers and breathtaking views of the Chicago River from its Avondale taproom.

Watch the Neo-Futurists perform 30 plays in 60 minutes

Instead of taking a chance, establish a happy medium between the two at The Neo-Futurist Theater in Andersonville, where the Neo-Futurists have been reinventing the bounds of live theatre for more than 30 years.

Plays may be lengthy and stuffy, while comedy acts can fall flat. The Infinite Wrench, the company’s flagship production, crams 30 short plays into a single 60-minute performance, frequently to moving and ludicrous effect.

Explore your shared musical tastes at 606 Records.

Although you don’t have to share the same tastes in music with the person you’re dating, it helps to like some of the same bands or genres.

At 606 Records, where you can discover releases from daring local and international labels among vintage rock and soul LPs, stock up on some songs you can listen to together. A Mr. Bongo reissue or a Numero Group collection can be the ideal music for your upcoming supper.

Hit a bullseye while axe-throwing

Although axe throwing has become increasingly popular recently, don’t rule it out as an interesting (though rather intense) date idea.

Bring snacks and non-alcoholic drinks to test who has the more muscular arm. Also, check the company’s website to see if one of the two Chicago sites is open for walk-ins.

Share some smoked shrimp at Calumet Fisheries.

What could be more romantic than making the trip to the Illinois border to sample some of this renowned shack’s smoked fish? Calumet Fisheries has offered catfish, shrimp, and salmon for over 70 years.

It’s a takeout-only establishment, so you’ll need to find a place to split your food, whether in your car or on the 95th Street bridge prominently featured in The Blues Brothers.

Split a flight of small-batch spirits at Koval Distillery

When ordering drinks that seem stale, consider mixing up your date night drinking a bit. You may purchase flights of the distillery’s small-batch spirits to enhance your tasting experience in the hip, ’70s-inspired surroundings of Koval Distillery’s new Ravenswood tasting area.

Select a whisky, gin, or one of the intriguingly flavoured liqueurs from the bar’s assortment while relaxing on comfortable leather couches (including rosehip, coffee, chrysanthemum, and honey).

Take a long walk on the North Shore Channel Trail.

You might idle away the time with your date while sitting around, or you could go for a walk and enjoy the surroundings. The North Shore Channel Trail travels along the Chicago River toward Evanston and has several excellent stops.

Depending on how far you’re willing to travel, you may stop at Lincolnwood Town Center, enjoy the artwork at Skokie Northshore Sculpture Park, or wind up at the Bahá’s House of Worship in Wilmette (you’ll probably get there faster on a bike).

Go bargain hunting at Monarch Thrift Shop.

This well-liked secondhand shop in Avondale has everything from new clothes to used books, and the revenues help individuals who are homeless and recovering from addiction.

On the Monarch Thrift Shop website, schedule a day for two people, and then show up prepared to get some savings on various gently used products.

Try to hit a strike at Avondale Bowl.

Although walk-ins are permitted, you and your date are best off making an appointment to play a few games at this retro-style bowling alley in Avondale because it gets pretty busy on the weekends and evenings.

There isn’t a digital scorecard in sight here, so you’ll need to do some simple math when you bowl, but the retro atmosphere (and the fully stocked bar in the rear) make it worthwhile.

Find new reads at 57th Street Books.

If you have already answered the opening questions (Where are you from? How do you behave? What’s your family like?” they converse quietly at Hyde Park’s 57th Street Books.

Browse several books together and secretly determine what you both want to buy at this large yet friendly store, which is praised for its outstanding collection of local writers.

Take advantage of a free museum day.

Did you know that the Shedd Aquarium and the Art Institute of Chicago are free attractions for viewing works of art and tropical fish?

Illinois residents may take advantage of free museum days at some of the city’s major institutions with a little advanced effort and research. Browse future free days or go to a museum or zoo anytime, which is always free.

Book a tour at The Plant.

Trying to win over a green date?

Every Sunday, the staff at The Plant, a former meatpacking plant in Back of the Yards now home to a group of food companies focusing on sustainability, conduct tours of the building’s facilities to give visitors a behind-the-scenes look at its waste-reduction strategy.

Online reservations are required; following, stay for a free tour of the Whiner Beer Company.

Romantic Date Ideas For Valentine’s Day in Chicago

Valentine’s Day is quickly approaching, and luckily, the Windy City offers everything you’ll need to light up the night with romantic riverfront vistas, Michelin-starred restaurants, and spectacular city lights.

Our collection of romantic date ideas includes something for everyone, whether you’re searching for the ideal romantic restaurant, want to spice things up with comedy or a concert or want something a bit more lowkey.

Is Valentine’s Day this year not your thing? Visit our Bad Blood Break-Up Bar, where you can drink, sing, and dance to timeless Taylor tunes. Valentine’s Day is an excellent opportunity to get the team together and treat yourselves to a memorable supper.

Alternatively, you can go to a dinner party for Galentine’s Day with adorable decorations and fun cocktails. Another option is to gather your friends for brunch at a Chicago location that serves mimosas and bloody marys.

Play Love Pong at SPIN Chicago

SPIN is the original ping pong social club because it combines an uncommon fusion of design, sport, and entertainment.

Go out with your significant other for a night of friendly rivalry that includes DJs, speciality drinks, unexpected acts, and more! Tickets include access to ping-pong tables, paddles, limitless balls, DJs, dancing, and more for two hours.

Where: 344 N. State St., Chicago, IL

Go for a Wine Tasting at Uvae Kitchen & Wine Bar

Uvae Kitchen & Wine Bar in Andersonville is a great place to unwind with a glass of wine.

On Saturday, February 11, at 3 p.m., Uvae will host a Valentine’s Day wine tasting showcasing “Sweetheart Wines” at the nearby Fromagerie & Tasting Room.

Guests may learn about the celebration’s origins with four 4-ounce wine pours, tiny nibbles like Duck Pâté, and a cheese platter.

Uvae will provide a five-course Valentine’s Day Wine Pairing Dinner that includes oysters in three ways: lobster bisque, king salmon, and a petit filet for a more lavish Valentine’s Day experience.

A white chocolate soufflé with white chocolate, strawberry crème anglaise, Bischoff, and meringue will be served for dessert.

Where: 5553 N. Clark St., Chicago, IL

Get Creative at a Couples Spray Paint Workshop

Bring out the street artist inside! During this interactive session intended for couples, you and your significant other will have the chance to make your unique item. Additionally, you’ll learn the tricks of the trade for using stencils and spray paint.

Not the most artistically inclined individual? Be at ease; Studio W.I.P. artists and staff will be in charge of this session and are eager to assist. Couples who paint together stay together, always!

Where: The Graff: 3527 W. Grand Ave, Chicago, IL

Experience a Fancy Tasting Menu

A husband-and-wife team of culinary masters developed the exclusive eatery Esmé, situated in Lincoln Park.

This exceptional restaurant’s Valentine’s Day tasting menu will highlight opulent dishes and ingredients like white truffles, burned onion consommé, white sweet potato ice cream, osetra caviar return, and more.

For $150 per person, diners may choose from a four-course meal at Bar Esmé (located in the same area). The menu includes Duck Ravioli, Monk Fish a la Normandie, wagyu au poivre, and more.

P.S. Esmé, which means “beloved” in French, puts this date night venue off the charts in the romance department. As if the sumptuous food and husband and wife combo aspect weren’t enough, they are married.

Where: 2200 N. Clark St, Chicago, IL

Make and Sip Valentine’s Cocktails

Check out a unique drink experience with a Valentine’s Day theme. Gold Coast Social will be adorned for Valentine’s Day, and you and your partner will get to mix two unique celebratory drinks. After blending, savour your beverages with a flatbread with a Valentine’s Day theme.

Where: Gold Coast Social: 7 W Division St, Chicago, IL

Share a Heart-shaped Pizza

If you want to escape the dinner crowds but still want to spend a romantic evening together, there is always the perennial favourite: heart-shaped pizza.

Plan a romantic movie night at home with your significant other, light some lights, and get out the champagne or bubbly to go with your celebratory pizza.

Order Valentine’s Dinner for Two from Sfera. The menu includes cannoli, a Sfincione in the shape of a heart, appetizers, salads, and cocktail bases for making cocktails at home.

Alternatively, you could surprise your lover with their preferred pizza from Robert’s in the shape of a heart (you can even get an ice cream heart pizza!).

Bartoli’s, Lou Malnati’s, Giordano’s, Eataly, Homeslice, and Dimo’s are other eateries offering heart-shaped pizzas (in-person and for delivery).

Where: Various locations.

Make Your Candles

Manufacturing your candles creates the perfect ambience. You may choose from various containers, smells, and additives in an instructor-led session before measuring, mixing, and pouring your candle.

As this activity is BYOB, feel free to have a glass of wine while you wait for your candle to burn down, then take it home and settle in for a romantic evening. Bonus: You’ll be reminded of your date every time you light it up.

Where: 4999 Old Orchard Center, Unit K11, Skokie, IL 60077

Take a Cooking & Cocktails Class Together

Try attending a cooking class together if you want something more engaging than supper. You may learn a new skill and enjoy excellent food. Visit the Fairmont Lodge’s cooking and cocktail classes with your special someone.

From 6:00 p.m. to 8:00 p.m., learn how to prepare well-known meals and drinks from Fairmont Chicago’s staff of brilliant chefs and neighbourhood mixologists.

Each session will focus on making favourites, such as fresh pappardelle pasta, an innovative drink (with a recipe given so you can make it at home), and a cheese and charcuterie platter.

Where: 200 N Columbus Dr, Chicago, IL

Explore a Museum or Gallery Together

Exploring art in a museum with a friend and learning something new is endearing. The Art Institute is a classic that features top-notch artwork and romantic locations like the Tiffany window.

Explore the many art galleries in River North or head to the Adler Planetarium to discover if you and your date are meant to be.

Where: Various locations.

Sip Champagne at 3 Arts Club Cafe

Don’t let the fact that this upscale restaurant is located within a Restoration Hardware store deceive you into believing it lacks romanticism.

The gorgeous atmosphere in the atrium, surrounded by glass and glowing lights, is the ideal dark setting for a romantic date night. You can have a memorable evening by selecting a bottle from their extensive wine range.

Where: 1300 N Dearborn St., Chicago, IL

Laugh the Night Away at a Stand-Up Comedy Show

Who said love had to be dull? Attend a fun comedy performance with some of today’s top celebrities to laugh off any date night anxieties.

Laugh Factory will present a Valentine’s special on February 14. The legendary stage will be decorated to celebrate the occasion. These regional comics, many of whom have performed in legendary venues, will cater to every taste and humour style!

Where: Laugh Factory: 3175 N Broadway, Chicago, IL 60657

Share Fondue by the Fire at Geja’s Cafe

There are fancy dinners for two, and then there’s Geja’s.

The Valentine’s Day special at one of Chicago’s most romantic restaurants includes an appetizer of Swiss Gruyere cheese fondue with a variety of bread, fruits, and vegetables for dipping, as well as an entrée of beef tenderloin, Australian lobster tail, and Gulf shrimp.

Geja’s Belgian Chocolate Fondue flamed tableside and provided with marshmallows for toasting, completes the meal.

Where: 340 W Armitage Ave., Chicago, IL 60614

See a Live Show at a Hidden Speakeasy

Slipping into a secret speakeasy is one of the sexiest feelings. The sensual atmosphere of Pigalle and Montmartre in Paris inspired Bordel, a cocktail bar and lounge.

After going through the secret entrance and up the leopard-print stairs, you and your partner will enter the opulent candlelight lounge, which features pink velvet sofas and draperies, tasselled chandeliers, and intricate bronze sconces.

Enjoy unique beverages with top-notch jazz musicians, burlesque performers, flamenco artists, magicians, cabaret dancers, and DJ performances every night of the week.

Where: 1721 W Division St., Chicago, IL

Attend a Beauty and the Beast Cocktail Experience

Is there anything more romantic than a true-to-life storybook romance? Give the gift of tickets for this immersive drink experience that combines an escape room, a theatre performance, and an adventure.

Guests are invited to a 90-minute voyage into the magical and cursed world of Beauty and the Beast, based on the Jeanne-Marie Leprince de Beaumont legend. Put on your best exquisite Victorian-inspired attire and take part in making two speciality drinks, resolving puzzles and obstacles, and more!

Where: Esmerelda’s Lounge: 2539 W Division St., Chicago, Illinois 60622

Take a Pizza Making Class and Sip Wine

At this DIY Pizza and Sip class at Millennium Hall, you can spend a memorable evening cooking homemade Neopolitan pizzas while consuming your preferred beer or wine.

You can choose from various toppings, sauces, meats, and cheeses before selecting anything from the open bar and enjoying some great one-on-one time and conversation. You can eat the pizza together at the restaurant or take it home when it’s done.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602

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