BEST Date Ideas in Chicago (for Date Nights + Day Dates)

Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas whether looking for the most romantic things to do in Chicago for couples on a date night or unique and fun first or second date ideas. From free and cheap date ideas for those on a budget to special date ideas for those looking to impress, you will find the perfect spot for every type of date.

Best Date Ideas in Chicago

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Unique Date Ideas in Chicago

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. Some upcoming concerts include:

Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to Adele
Candlelight: An Acoustic Tribute to David Bowie
Candlelight: A Tribute to The Miles Davis Classic Quintet
Candlelight: The Best of Hans Zimmer at Music Box Theatre

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

Listen to Concerts Under The Stars

If you prefer to listen to music outdoors, Sinatra Under the Stars at the Hyatt Centric The Loop is an intimate rooftop concert.

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.

Watch Movies on a Rooftop

Want to watch movies on a rooftop against the backdrop of the Chicago skyline? Rooftop Cinema Club, located 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 see what movies are playing and purchase tickets in advance here.

Spray Paint ‘n’ Sip Urban Art Workshop

Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.

Where: Studio W.I.P. at The Chicago Kedzie Plaza, 800 North Kedzie Avenue, Unit 208, 60651

Cost:  $40 per person for adults. Click here to purchase tickets.

Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières featured in Emily in Paris (one of my favorite travel shows on Netflix), the popular Immersive Van Gogh Exhibit is a massive indoor digital presentation of Vincent Van Gogh’s artwork. You can also book date night packages which include access to a private Juliet balcony, chocolate truffles, champagne and a handcrafted floral arrangement.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago

Cost:  Tickets start at $39.99 plus fees for off peak times. You can see full prices and purchase tickets in advance here.

Immersive Monet & The Impressionists

Immersive Monet & The Impressionists is the latest blockbuster immersive art experience by Massimiliano Siccardi, whose Immersive Van Gogh exhibit sold over 4.5 million tickets in North America. From Monet’s celebrated water lilies to Degas’s graceful dancers and more, step inside living paintings at Immersive Monet & The Impressionists. you can also book date night packages which include access to a private Juliet balcony, chocolate truffles, champagne and a handcrafted floral arrangement.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago

Cost:  Tickets start at $29.99 plus fees for off peak times. You can see full prices and purchase tickets in advance here.

Take an Architecture River Cruise

An architecture river cruise is a must on any Chicago bucket list for locals and visitors alike.

Take a Lake Cruise

lake cruise is a great date night idea in Chicago
A lake cruise is perfect for a romantic date in the summer. 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.

Hold and Feed a Bunny

Looking for a unique indoor thing to do in Chicago? Visit the Cuddle Bunny (2901 N Clark St) where visitors can pet and feed bunnies.  Cuddle Bunny also hosts special events like yoga and story time. You can read more about the experience here.

Fun Chicago Date Ideas

Play Indoor Mini Golf

Play mini golf at Big Mini Putt Club (1302 N Milwaukee Ave, Chicago, IL 60622), a 9-hole indoor miniature golf course with a full bar serving craft cocktails, local draft beers, and other drinks.

Go Indoor Skydiving

Go indoor skydiving at iFLY Chicago – Lincoln Park (800 W Scott St).

Have Fun at Navy Pier

outdoor rides at Navy Pier fun date idea in 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:

Museum of Ice Cream

Chicago’s newest attraction, the Museum of Ice Cream (Tribune Tower, 435 North Michigan Ave) is a cute date idea. 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. You can see full prices and purchase tickets in advance here.

Museum of Illusions

The Museum of Illusions Chicago (25 E Washington St) offers an interactive, immersive and fun experience. Visitors can engage in over 80 astonishing and mind-bending exhibits that will teach you about vision, perception, the human brain and science. You can buy a timed entry ticket here.

Visit the Color Factory

Color Factory (320 W Jackson Blvd) is a new interactive art museum located on the lower level of Willis Tower. Named one of the 22 Best New Experiences in the World in 2022 by Time Out, the Color Factory is a sensory celebration of color, with interactive installations, immersive rooms and carefully curated moments inspired by the city of Chicago including its signature ball pit and confetti room.

Push Pin Travel Maps

Most Romantic Chicago Date Ideas

These romantic date ideas are perfect for an anniversary date, birthday, Valentine’s Day or other special date.

Take a Helicopter Tour

If you are able to splurge, a helicopter tour is the ultimate date night activity.

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

Free or Cheap Date Ideas in Chicago

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.

Look for Street Art

Another fun active date activity 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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

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 is a good free date night idea
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.

Walk the Lakefront Trail

walking and relaxing on the Lakefront Trail

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.

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 Lincoln Park Zoo

Lincoln Park Zoo (2400 N. Cannon Drive) is another good date spot for a daytime date. During the Christmas holiday season, you can visit the zoo during Zoolights after hours in the evening.

More Great Date Ideas in Chicago

Still looking for date ideas? Here are more good date ideas in Chicago.

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.

Art Institute of Chicago

The Art Institute of Chicago (111 S Michigan Ave) is a great choice for a daytime date but it has extended hours (until 8 p.m.) on Thursdays. In addition to its large permanent collection of art from around the world, you can see rotating exhibitions.
Click here to buy a skip the line ticket if you want to avoid long lines.

Adler at Night

The Adler Planetarium is open late every Wednesday night (until 10:00 pm). Experience hands-on, minds-on activities, experiences, and shows about the universe and see their award-winning sky shows. Every Wednesday is free Museum Entry for Illinois residents with proof of residency. Tickets must be purchased online in advance.

Tip:  If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Shedd Aquarium

The Shedd Aquarium is another fun daytime date but it is also open late on select days in September 2022. Extended hour days correspond with Illinois Resident Free Days so Illinois residents can visit for free.

Go Kayaking in the River

Active couples might enjoy kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders. There are several tours to choose from including sunset tours, moonlight tours and fireworks tours. Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

Have Dinner at an Intimate Restaurant

Some of the most romantic restaurants in Chicago to take your date 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.

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 best 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.

What are your favorite date spots in Chicago?

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