18 Romantic Things to Do in Chicago for Couples

This post on romantic things to do in Chicago is by Umesh Kumar.

Ah, Chicago.

The Windy City. The Second City. The City of the Big Shoulders.

The City of…Love?

No, wait. That’s not right.

In actuality, though, it’s not an outlandish assertion. If you know where to search, as you will be the conclusion of this essay, there are many romantic things to do in Chicago.

Having twice been named the most fantastic large city by Condé Nast Traveler (yep, surpassing New York), Chicago undoubtedly deserves a place on your list of places to visit. Here are 18 additional justifications for romantic things in Chicago, just in case you need more persuading.

THE TOP ROMANTIC THINGS TO DO IN CHICAGO, ILLINOIS

1. INDULGE IN SOMETHING SWEET

Without question, Chicago is a gourmet metropolis, and sweet delights are undoubtedly a part of the mix. Gourmet donuts are famous in Windy City, and you may choose from various businesses that produce fried dough. To counteract the sweet lemon pistachio old-fashioned doughnut from Stan’s (my personal favorite), grab a steaming cup of coffee. For even more options, see this list of the finest donut shops in Chicago. Why not attempt each one?

Visiting during the wintertime? Visit Mindy’s Bakery to sip fine hot chocolate with substantial handmade marshmallows. Visit for the hot cocoa and remain for breakfast. This is an ideal addition to your list of romantic things to do in Chicago during the winter!

Additionally, a sizable tub of the city’s renowned Garrett popcorn is always a good choice. Get the Garrett mix, caramel, and cheddar cheese-coated popcorn, which is a sweet and salty combination. This would be the perfect present for a loved one back home!

2. SEEK OUT CHICAGO-STYLE PIZZA

Go behind the scenes of Chicago’s deep-dish pizza while spending time preparing a great lunch with your honey. Sure, you could go out and get a tasty piece of deep-dish pizza from Chicago, but for a genuine adventure, enroll in a class and bake the pizza yourself.

Alternatively, go on a pizza tour and spend a few hours visiting several pizzerias. Choose the pizza slice that both of you enjoy the most, then have a box delivered to your house so you can remember the experience afterward.

3. SEE THE CITY LIGHT UP FROM ABOVE

A rooftop bar is a definite must-do when it comes to romantic things to do in Chicago.

As you might expect, Chicago has many rooftop pubs with breathtaking views. Around sunset, go to Cindy’s Rooftop, part of the Chicago Athletic Association Hotel. A drink in hand, walk to the balcony for sweeping views of Millennium Park, the Art Institute, and the lake (may I suggest the Grey Garden?).

If you are not averse to heights, The Signature Lounge, located on the 96th story of what was originally the John Hancock Center, is a must-visit. Drink a beverage as the entire city is lit and stretched below you. Don’t forget to photograph the view from the women’s toilet to show your sweetheart, ladies! It is regarded as one of the city’s top vistas.

Feeling peckish? Have a romantic dinner at The Signature Room, one floor down.

4. CATCH SOME LAUGHS

A little humor goes a long way in preserving your relationship’s lighthearted side. Not only are Steve Carell and Tina Fey two of the many well-known comedians that Chicago has produced, but many of them began their improv careers at Second City.

Laugh the night away with your special someone at this venerable Chicago-area comedy club. Enjoy some food and beverages while admiring the fearless improvisers. One of the best date night options in Chicago is this one.

5. BE ACTIVE TOGETHER

Do you feel restless? Don your skates and head to the Maggie Daley Park Skating Ribbon if you’re in Chicago during the winter. As you float through a winter wonderland with couples and families nearby, the city’s skyscrapers will soar majestically around you.

Alternatively, visit Starved Rock for the day. You may discover a peaceful getaway from the noise and bustle of city life in less than a couple of hours of driving. Hike the park’s lovely pathways and enjoy waterfall views while you’re at it.

If you prefer to travel by foot, don’t forget to window shop on Michigan Avenue. This boulevard, often known as The Magnificent Mile or Mag Mile, is studded with posh stores. You may stroll hand in hand down the city’s River Walk, stopping at various establishments for wine, gelato, or even sit-down meals while riverboats pass by. This is such a cute thing to do in Chicago!

6. GO TO A SPORTS GAME

Would you want to keep it quieter? Instead, see others being active! Seeing the Cubs, White Sox, Blackhawks, Bulls, and Bears play is one of the best activities for couples in Chicago because it is home to several fantastic sports teams!

Whatever sport you enjoy, Chicago probably has a team worth following. Go to a game dressed in the colors of the host team. Together, support a team, and don’t forget the refreshments!

7. LISTEN TO THE MUSIC

Chicago’s music frequently reflects its romantic side. Enjoy mellow jazz at Green Mill, formerly Al Capone’s favorite hangout. (Spoiler alert: take this tour to learn more about Chicago’s gangster past.)

Nowadays, a laid-back atmosphere and excellent music are vital components. Kingston Mines is a popular favorite for additional jazz and blues music. Get ready for a calm, musical night out in town.

Not really your thing, the blues and jazz? Instead, consider the Chicago Symphony Orchestra. Or, for something more lively, see a live band at The Vic Theater.

8. TAKE A RIVER CRUISE

There is no better way to appreciate Chicago’s architecture than taking one of the city’s architectural river excursions. Feel the wind in your hair as you pass through picturesque city landscapes as your guide explains the history of the majestic structures around you. This has to be among the top Chicago romantic date suggestions.

9. UNWIND AT A THERMAL SPA

Aire Ancient Baths is a conserved structure that delights with its exposed brick and industrial columns. It offers a magnificent experience. Spend money on a massage, a dip in red wine, or another relaxing ritual with your special someone. This is a fantastic opportunity to unwind and deepen closeness during your romantic trip to Chicago!

10. SEE THE STARS AT THE ADLER PLANETARIUM

Create memories at the country’s first planetarium. The planetarium frequently hosts astronomical performances and artistic gatherings like Sun Salutation Yoga or Adler After Dark. Together, look at the astronomy exhibits, and don’t forget to stroll outdoors for a breathtaking view of the Chicago skyline and a look at the real stars!

A delightful trip to the Adler screams romance in Chicago, frequently reserved as a favorite wedding location.

11. ENGAGE IN FRIENDLY COMPETITION AT GUTHRIE’S TAVERN

Hunker down with a board game and a beer at this local bar that’s all about laid-back fun… Nothing ignites a conversation over Guthrie’s cheese pizza and cold beverages like some friendly competition. Or hot tea or coffee if that’s your style.

A fantastic option for fun things to do in Chicago for couples!

12. EXPLORE AN UPSCALE FOOD HALL

Visit one of Chicago’s trendy food halls, Revival or Chicago French Market, for a speedy, elegant lunch. Select a few meals from various restaurants to make a fun-tasting menu. There is no better way to agree on where to eat if you and your companion have varying culinary preferences.

13. WATCH THE BUCKINGHAM FOUNTAIN LIGHT UP

When the sun has fallen, visit Grant Park’s Buckingham Fountain for a spectacular light display. The Latona Fountain at the Palace of Versailles inspired the enormous fountain, among the biggest in the globe. The fountain performs a stunning water and light show for 20 minutes every hour from May until mid-October.

The fountain’s water and light show are even more impressive when the city skyline is illuminated. This Chicago location is quite lovely.

14. VISIT NAVY PIER AND WATCH THE FIREWORKS

Navy Pier is an excellent place to spend some time, even if it is touristic, enjoying a leisurely walk along the waterfront or riding the Centennial Wheel. Additionally, you may witness a spectacular fireworks show from Memorial Day to Labor Day. Catch the performance at 9:30 p.m. on Wednesdays or at 10:15 p.m. on Saturdays if you’re in town. This is one of the most excellent things to do in Chicago with a partner, tourist or not!

15. SPEND TIME ON THE BEACH

Chicago’s shoreline is gorgeous and one of the city’s most romantic locations. Sand and a lake are on one side, while the skyline of a metropolis is on the other. Together, you may stroll, jog, ride a bike, or relax on the sand while listening to the sound of the waves smashing.

16. HAVE A PICNIC AT MILTON LEE OLIVE PARK

Milton Lee Olive Park is a little treasure that offers a more sedate area to play on a good day. Bring a picnic, spend a few hours catching up on life, and enjoy the scenery while admiring the Navy Pier nearby. In Chicago or elsewhere, picnics are a timeless romantic activity for couples.

17. ENJOY MOVIES OR MUSIC IN MILLENNIUM PARK

At Millennium Park, there is beauty wherever you look. If you go during the summer, be sure to see a performance at the Jay Pritzker Pavilion. Bring wine and snacks, a picnic blanket, or lawn chairs for a relaxing evening outside.

18. BOOK A ROMANTIC CHICAGO HOTEL ROOM

There are many romantic hotels in Chicago, but The Viceroy is a standout option if you want to stay in a place with a rooftop bar, an outdoor pool, a superb on-site restaurant, and a prime location near the AIRE ancient baths. Everything about it screams traditional romance, especially if you add the date night package!

Click Here to Check Prices & Book!

When you think of the most romantic cities in America, Chicago might not immediately come to mind. Ultimately, it’s a city populated with friendly, diligent individuals who like excellent cuisine and good moments. You may be sure this town has everything you need for a romantic weekend away.