BEST Things to do in Chicago at Night (2024 Winter/Holidays Edition)

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 (2024)

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

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.

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 available in the evening.

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 candlelight concerts include:

A Tribute to Coldplay on Strings
Best of Bridgerton on Strings
Candlelight: A Tribute to U2
Candlelight: A Tribute to Rihanna

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

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 twice nightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Nightly projections run twice every night through December 30, 2024

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.

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

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 9pm Sunday-Thursdays and 10pm on Fridays & Saturdays

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

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. Newport Peek-Easy Burlesque Show is one of the best burlesque shows in Chicago.