Most Romantic Things to Do in Chicago for Couples

The most romantic things to do in Chicago for couples. Whether planning a weekend getaway in the city with your significant other or looking for unique Chicago date night ideas, these are the best activities to enjoy in Chicago with your partner.

Romantic Things to Do in Chicago for Couples

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Listen to Music at an Intimate Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Upcoming concerts include:

Candlelight: Romantic Jazz featuring Billie Holiday, Frank Sinatra, & Ella Fitzgerald
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Taylor Swift

You can find the full list of current candlelight concerts in Chicago here.

Listen to Concerts Under The Stars

Enjoy classical music concerts on a rooftop or a beautiful garden oasis. Upcoming Concerts Under The Stars include:

Sinatra Under the Stars at AIRE
ABBA Under the Stars at AIRE
Amy Winehouse: Jazz Under the Stars

You can find the full list of Concerts Under The Stars here.

Take a Helicopter Tour

If you are able to splurge, one of the best ways to see Chicago is from a helicopter tour.

Take an Architecture River Cruise

An architecture river cruise is a must on any Chicago bucket list. In addition to cruises throughout the day, there are also architecture river cruises at night for couples on a date night.

Take a Lake Cruise

skyline from lake cruise in Chicago at night
If you enjoy being on the water, a lake cruise is also a fun activity at night. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. If your time is short, you can do a combination river and lake cruise.

Watch Free Summer Fireworks on Wednesday and Saturday nights

Navy Pier puts on a free fireworks show every Wednesday and Saturday night between Memorial Day weekend and Labor Day.

While you can watch the fireworks from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.

Another great option for watching the fireworks is on a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.

Relax on the Riverwalk

The Chicago Riverwalk, located along the south bank of the Chicago River from Lake Michigan to west of Franklin Street, is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars and other places to sit and relax along the way. You can find a map of attractions on the Riverwalk here.

Watch Digital Art at Art on theMart

Art on the Mart in the evening
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown twice every night. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Enjoy the Views from 360 Chicago

360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has an observatory with great panoramic views of Chicago. The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. Click here to buy a skip the line ticket). You can also visit BAR 94 which has a full 360-degree view of Chicago.

If you prefer to enjoy the same views over a meal or a drink, there is an upscale restaurant on the 95th floor named the The Signature Room at the 95th, and a bar on the 96th floor called The Signature Lounge at the 96th which are open late in the evening.

Ride the Ferris Wheel at Navy Pier

outdoor rides at Navy Pier Chicago

Navy Pier has several fun outdoor activities at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).

Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises:

Watch the Water Displays at Buckingham Fountain

Buckingham Fountain in Chicago at night

Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. When the water is turned on, it produces a major water display with a center jet shoots water to a height of 150 feet into the air.

Couples should visit Buckingham Fountain at night when a light and music display accompanies the water display.

Visit the new Chicago: Museum of Ice Cream

Chicago’s newest attraction, Museum of Ice Cream is opening this month. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles.

Where: Tribune Tower, 435 North Michigan Ave, Chicago, IL 60611

Cost: You can see full prices and purchase tickets in advance here.

Look for Street Art

Another fun activity for couples is walking around the city looking for street art.

One of the most famous murals in Chicago is Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.

Listen to Free Outdoor Music Concerts

concert at Millennium Park Chicago
One of the best things for couples to do in Chicago in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

Grant Park Music Festival runs on Wednesdays, Fridays and Saturdays from June 14 -August 19, 2023 and offers both free and paid seating.

Watch Movies on a Rooftop

Want to watch movies on a rooftop against the backdrop of the Chicago skyline? Rooftop Cinema Club, on the fifth floor terrace of The Emily Hotel (311 N Morgan St in Fulton Market), is a high end outdoor movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including loveseats. Guests can also order drinks and snacks. You can purchase tickets here

Walk the Lakefront Trail

walking and relaxing on the Lakefront Trail, a romantic place in Chicago

What is more romantic than a walk on the beach? Couples can walk along the Lakefront Trail, a paved path on a 18-mile-long stretch along Lake Michigan.

There are numerous beaches along the way if you want to stop for a picnic on the beach. Don’t forget to pack your beach essentials!

Even if the weather is too cold to enjoy the beach, the Lakefront Trail has some of the best spots to sit down, relax and enjoy Chicago skyline views.

Here is a map of the Lakefront Trail as well as its access points.

Relax in Thermal Baths at AIRE Ancient Baths

Relax and enjoy thermal baths, massages and exclusive rituals with your loved one at AIRE Ancient Baths Chicago. Inspired by the tradition of baths from ancient Roman, Greek and Ottoman civilizations, AIRE Chicago is located in a restored historical building lit by candlelight in River West.

Where: AIRE Ancient Baths Chicago, 800 West Superior St., Chicago, IL 60642

Visit a Conservatory

There are two conservatories in Chicago that make for a great warm escape on a cold or rainy day.

The Garfield Park Conservatory (300 N. Central Park Ave) is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.

The Lincoln Park Conservatory (2391 N. Stockton Drive) is a public conservatory full of tropical palms and plants.

READ: Best Indoor Things to Do in Chicago for more indoor Chicago attractions.

Live Jazz & Dinner for Two

Have dinner for two with craft cocktails while listening to live music at Le Piano (6970 N Glenwood), a cozy, elegant, and romantic venue.

Dine in the Dark While Blindfolded

Looking for a unique dining experience? Dining in the Dark (Hubbard Inn, 110 W Hubbard) is a gastronomical experience that invites you to explore the full potential of your taste buds in a uniquely entertaining atmosphere. While blindfolded, you’ll enjoy delectable surprise dishes and feast on an entire meal without using your sight, thereby enhancing your other senses. There are three menus to choose from including a vegan option.

Have Drinks on a Rooftop

Have dinner and drinks at one of the city’s many rooftop bars and restaurants while enjoying amazing views. The most romantic rooftops in Chicago include:


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LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan.

The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.

Have Dinner at an Intimate Restaurant

Take your sweetie out for dinner at an intimate restaurant. Some of the most romantic restaurants in Chicago include:

North Pond (2610 N Cannon Dr) – Michelin star restaurant inside Lincoln Park with beautiful views.

Bavette’s Bar & Boeuf (218 W Kinzie St) -upscale steakhouse in an ornate, dimly lit wood and brick setting.

Ella Elli (1349 W Cornelia Ave) – Italian-Mediterranean sharing plates and classic cocktails in an intimate setting.

Geja’s Cafe (340 W Armitage Ave, Chicago, IL 60614) – fondue restaurant known for its romantic, intimate atmosphere.

Looking for more suggestions? You can find a list of the most romantic restaurants in Chicago here.

As you can see there are many romantic things to do in Chicago.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:




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