BEST Date Ideas in Chicago for Date Nights + Day Dates (2024)

Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas in 2024 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 (2024)

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Unique Date Ideas in Chicago

AirOtic Soirée: A Sensual Cirque Cabaret!

Take your significant other to AirOtic Soirée: A Sensual Cirque Cabaret!, a modern burlesque cirque cabaret where sultry performances blend with dazzling cirque acts featuring jaw-dropping and sultry acrobatics, accompanied by ambient music to set the mood. Only for adults 21+ with valid ID. AirOtic Soirée is only in Chicago for a limited time

Where: Joy District, 112 W Hubbard St, Chicago, IL 60654

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

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 Pink
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Beyoncé
Candlelight: Neo-Soul & Hip-Hop Favorites

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

Listen to Concerts Under The Stars

Enjoy a music concert on a beautiful rooftop with city views. Upcoming Concerts Under The Stars include:

ABBA Under The Stars at AIRE
Sinatra Under the Stars at AIRE
A Starlit Tribute to Taylor Swift at The Aire Rooftop
Queen: Rock the Aire! at the Aire Rooftop

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

Titanic: The Exhibition

Titanic: The Exhibition is a unique date idea in the Chicago suburbs. This interactive experience allows you to step inside recreations of the Titanic’s interior. Immerse yourself in the stories of its passengers, see hundreds of artifacts, and discover the tale of the design, creation, launch, maiden voyage, and tragedy of the historic ship.

Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

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

Take a Pottery Class

Discover the art of wheel-throwing potter with this course tailored for beginners. You can learn the basics of clay preparation, centering, and shaping and create your own unique pieces, from mugs to bowls and plates.

Hold and Feed a Bunny

Looking for a unique thing to do in Chicago? Visit the Cuddle Bunny in Chicago, where visitors can pet and feed bunnies.  Cuddle Bunny also hosts special events like yoga and story time.

Where: Cuddle Bunny, 2901 N Clark St, Chicago, IL 60657

Where: 917 W 18th St, Chicago

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.

Fun Chicago Date Ideas

Play Games at a Barcade

Chicago has several arcade bars where you can have drinks while playing arcade games including Logan Arcade (2410 W Fullerton Ave), Emporium Logan Square (2363 N Milwaukee Ave), Emporium Wicker Park (1366 N Milwaukee Ave), Headquarters Beercade (213 W Institute Pl) and Replay Lincoln Park (2833 N Sheffield Ave).

Play Indoor Mini Golf

Play mini golf with drinks at one of the several indoor miniature golf courses in the Chicago area.

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).

Watch a Drunk Shakespeare Play

Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.

Where: The Lounge At The Lion, 182 North Wabash Avenue

Cost:  Prices start at $29 per person. Click here to purchase tickets.

See a Magic Show

Take your date to a magic show. Chicago Magic Lounge (5050 North Clark Street) gets rave reviews. Another great magic shows is Trickery Chicago Magic Show (3453 N Halsted Street).

Laugh at a Comedy Show

If you want to make your date laugh, take them to one of Chicago’s many comedy clubs. Second City (230 W North Ave) is known for its many famous alums, including Tina Fey, Bill Murray, Chris Farley, Stephen Colbert and Steve Carell.

Other great comedy clubs include iO Chicago (1501 N Kingsbury St) and Laugh Factory Chicago (3175 N Broadway).

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.

Museum of Ice Cream

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.

Most Romantic Chicago Date Ideas

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

Watch Free Fireworks

summer fireworks in Chicago at night
Navy Pier puts on a free fireworks show twice a week between Memorial Day weekend and Labor Day weekend. 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.

You can see the fireworks on a tour like this fireworks and evening segway tour.

A romantic way to watch the fireworks is on a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.

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

Take a Candle Making Class

Looking for a unique and romantic date night during the weekend? Join this Couples Candle Making Class at Above Average Candle Studio (3414 West Foster Avenue) where you and your date can create a signature scented candle together or this candlemaking class in downtown Chicago at Reggie Hathorn (900 North Michigan Avenue, Level 6).

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

skyline from lake cruise in Chicago
A lake cruise is also a fun date idea. 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.

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.

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 nightly. 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.

You can rent SUP paddle boards at North Avenue Beach here and kayaks at Ohio Street Beach here.

There are numerous beaches along the way if you want to stop for a date 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.

Take a Water Taxi to Chinatown

A great cheap date idea is to take a water taxi to Chinatown. In addition to eating and walking around Chinatown, you can relax and enjoy Ping Tom Memorial Park, which has unique skyline views.


Visit Lincoln Park Zoo

Lincoln Park Zoo is one of a few free admission zoos in the United States.

Where: 2400 N. Cannon Drive

Have a Picnic at the Park

Chicago is full of parks and green spaces that are perfect for a romantic picnic including Lincoln Park, Ping Tom Memorial Park and Milton Lee Olive Park – all of which also have amazing city views.

Watch Free Outdoor Movies

Take your date to watch an outdoor movie for free. You can watch outdoor movies at Gallagher Way in Wrigleyville on select Wednesdays from May to end of September. Seating on the grass is free but you can also purchase VIP seating. You can find the full schedule of movies at Gallagher Way here.

This summer you can also watch free movies on Tuesday evenings from July 16–August 20, 2024 at Millennium Park. Guests can sit at the Jay Pritzker Pavilion or lounge on the Great Lawn as movies are presented on the state-of- the-art, 40-foot LED screen. You can find the full schedule for the Millennium Park Summer Film Series here.

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.

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.

Go Indoor Skydiving

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

Watch Movies on a Rooftop

Want to watch classic movies against the backdrop of the Chicago skyline? You can watch movies outdoors Rooftop Cinema Club, a rooftop located in Fulton Market.

Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St). This is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks.

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:




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