Looking for fun things to do in Chicago tonight? Below are the best things to do in Chicago at night. Whether you are visiting Chicago or have lived here all your life, you will find something unique and new to do in the city in the evening.
Best Things to do in Chicago at Night (2025)
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Below are the top things to do in Chicago in the evening.
Join a Mob or Crime Tour
Chicago is known for its history of organized crime and being the home of mafia figure Al Capone. There are several fun mob tours in the evening for those that want to learn more about the history of organized crime.
Kayak in the Chicago River
A fun an active way to enjoy city views is to go kayaking in the Chicago River.
You can join a guided kayaking tour in the river in the evening including this sunset kayak tour and this moonlight paddle tour. Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Listen to Concerts Under The Stars
Enjoy a music concert on a beautiful outdoor rooftop with city views. Upcoming Concerts Under The Stars this summer include:
ABBA Under The Stars at AIRE
A Starlit Tribute to Taylor Swift at The Aire Rooftop
Piano Men: A Billy Joel & Elton John Tribute at the Aire Rooftop
You can find the full list of Concerts Under The Stars here.
Listen to Music at an Intimate Candlelight Concert
If you prefer being indoors, Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Upcoming candlelight concerts include:
Candlelight: Tribute to U2
Candlelight: Tribute to Queen and More
Candlelight:The Best of Hans Zimmer
Candlelight: Tribute to Fleetwood Mac on Strings
You can find the full list of candlelight concerts in Chicago here.
Take an Architecture River Cruise
Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise. In addition to cruises throughout the day, there are also architecture cruises in the evening.
Watch Free Fireworks
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 show from Navy Pier, you can also watch it from various spots along the Lakefront.
A great way to watch the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.
9pm on Wednesdays and 10pm on Saturdays
Relax on the Riverwalk
The Chicago Riverwalk, a 1.25-mile long path along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. It is one of the best spots in Chicago for boat and people watching. There are restaurants, bars, benches and steps to sit and relax. You can see a map of attractions on the Riverwalk here.
Open until 11 p.m. daily
Watch Digital Art at Art on theMart
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 every night on Thursdays through Sundays. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
9:00-9:30pm on Thursdays through Sundays
Have Fun at Navy Pier
There are fun attractions at Navy Pier in the evening including restaurants, bars, rides and games and a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).
You can also check out the new Flyover Chicago, an immersive flyover experience.
Open to 8pm Sunday-Thursdays and 9pm on Fridays & Saturdays
See the Water Displays at Buckingham Fountain
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 for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
Buckingham Fountain runs to 11:00 p.m. daily from mid-May to mid-October.
Listen to Free Music in Millennium Park
A great activity during warm summer nights is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The Grant Park Music Festival runs from June 11-August 16, 2025 and the Millennium Park Summer Music Series takes place on Mondays and Thursdays from June 26-August 7, 2025.
Watch Free Movies in the Park
You can watch free movies every Tuesday night (from July 1–August 19, 2025) near The Bean at Millennium Park on the state-of- the-art, 40-foot LED screen.
There are several more places you can watch free outdoor movies in Chicago in the evening including Gallagher Way in Wrigleyville and various Chicago public parks.
Watch Classic Movies on an Outdoor Rooftop
Want to watch classic movies against the backdrop of the Chicago skyline? Check out Rooftop Cinema Club outdoor screening series to a rooftop in Fulton Market.
Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) and 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. You can purchase tickets in advance here.
Shop and Eat at a Night Market
The Argyle Night Market is an annual event that features food from local Argyle restaurants plus live cultural and musical performances on Thursday evenings each summer (5-9pm from July 3–August 28, 2025).
There is also a night market at Gallagher Way in Wrigleyville on select Thursday evenings (4-8pm) in the summer.
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. You can also visit BAR 94 which has a full 360-degree view of Chicago.
Click here to buy a skip the line ticket.
Enjoy the Views from the Skydeck at Willis Tower
The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998. If you are not scared of heights, stand on The Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower!
Click here to buy a skip the line ticket.
Open until 8pm on weekdays and 10pm on weekends
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. Click here to purchase tickets.
6 p.m. & 8:30 p.m. Wednesdays – Sundays
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 Famous Works of Art at the Art Institute of Chicago
The Art Institute of Chicago (111 S Michigan Ave) is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. 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.
The museum is open until 8 p.m. on Thursdays.
Museum of Illusions Chicago
The Museum of Illusions Chicago (25 E Washington St) offers an interactive, immersive and fun experience for both adults and kids. 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.
Museum of Illusions Chicago is open until 8 p.m. on Sunday – Thursday and 10 p.m. on Friday and Saturday.
Take a Walking Ghost Tour in Lincoln Park
Take a walking ghost tour of Lincoln Park to learn about the city’s haunted past and visit the sites of some of the most gruesome disasters and murders in Chicago’s history.
Adler at Night
The Adler Planetarium is open late every Wednesday night. 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.
Open late on Wednesdays from 4:00 pm–10:00 pm
Admire Chicago’s Skyline
Chicago has an amazing skyline and it is even more beautiful at night when it is all lit up. Here are the best places to visit in Chicago for skyline views.
Have Dinner and Drinks on a Rooftop
Chicago has several rooftop bars and restaurants with amazing views of Chicago. Here are some of the best rooftops in Chicago:
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.
See a Magic Show
Join Trickery Chicago Magic Show (3453 N Halsted Street) and Chicago Magic Lounge (5050 North Clark Street).
Listen to Live Jazz Music
Listen to live jazz music at a historical Chicago spot. The Green Mill Cocktail Lounge (4802 N Broadway) is known for its live jazz and its connection to Chicago mob history. It was a prohibition era speakeasy and one of Al Capones favorite spots to hang out.
Listen to the Blues at Kingston Mines
Kingston Mines is the oldest blues bar in Chicago and has hosted blues legends like Magic Slim, Koko Taylor and Joanna Connor since opening in 1968.
See a Burlesque Show
For adults looking for some sexy fun, a burlesque show is a unique evening activity. The Newport Peekeasy: Burlesque and Variety Show is one of the best burlesque shows in Chicago.
Visit an Escape Room
An escape room is a fun date activity. You and your date will work together to find clues, solve puzzles, and complete a mission with this escape room game.
Have a Hot Dog at Wieners Circle
Stop by Wieners Circle, the iconic hotdog stand known for its late night verbal abuse and crude humor between the customers and the employees.
Open to 1:00 am Sunday to Tuesday, 2:00 on Wednesdays and Thursdays, and 4:00 on Fridays and Saturday
Play Indoor Mini Golf
Play indoor mini golf at night with drinks in a fun, lively setting at several indoor mini golf courses in and around Chicago.
Play Games at a Barcade
Chicago has several arcade bars where you can combine drinking with 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).
Gamble in Chicago’s Only Casino
Bally’s Casino Chicago (600 N Wabash Ave, Chicago, IL 60611), the only casino located in the city, is open 24-7.
Eat at a 24 Hour Diner
If everything else is closed you can always have a meal at a 24 hour diner. As long as you order food and refill your drinks you can usually stay for several hours. Some of the best 24 hour diners in Chicago include:
Diner Grill (1635 W Irving Park Rd)
Golden Nugget Pancake House (2406 W. Diversey)
The Golden Apple Grill & Breakfast House (2971 N Lincoln Ave).
Relax in a Korean Spa
King Spa & Sauna (809 Civic Center Dr. Niles, IL 60714) is a Korean spa that is open 24 hours, 7 days a week. In addition to spa services there is a food court as well as chairs and beds for an overnight stay. It is located in a nearby suburb of Chicago located about 8 miles from Chicago O’Hare Airport and 15 miles from downtown chicago.
As you can see there are many fun and unique things to do at night in Chicago.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
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