BEST Things to do in Chicago at Night in 2024 (From a Local!)

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)

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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.

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.

Take a Lake Cruise

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 especially around sunset.

If your time is short, you can do a combination river and lake cruise.

Listen to Concerts Under The Stars

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

Sinatra Under the Stars at AIRE
Amy Winehouse Under The Stars

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

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 Taylor Swift
A Tribute to Beyoncé at Music Box Theatre
A Tribute to Coldplay on Strings
Best of Bridgerton on Strings

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

Have Fun at Navy Pier

Navy Pier is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier 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.

Make sure to come back or stay for the free fireworks every Wednesday and Saturday night.

Open to 10pm Sunday-Thursdays and midnight on Friday & Saturday

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 nightly through December 30, 2024

Go Kayaking in the River

A fun and active way to explore the city is to go 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.

Take a Night Tour

If you are visiting Chicago for the first time, you can join a night tour to see a different side of the city. Exploring Chicago after dark is more pleasant when the weather is hot in the summer as you can avoid the heat and strong sun. Check out this 75-minute Night Bus Tour.

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 10pm

Watch Free Outdoor Movies

There are several places you can watch free outdoor movies in Chicago in the evening. You can watch free outdoor movies at various public parks throughout the city.

Watch Classic Movies on a Rooftop

Want to watch classic movies against the backdrop of the Chicago skyline? Rooftop Cinema Club’s outdoor screening series on a rooftop located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) in Fulton Market. 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.

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 until mid-October.

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 Ghost Tour

Explore Chicago while learning about its haunted past and visiting the sites of some of the most gruesome disasters and murders in Chicago’s history.

This haunted segway tour and Halloween bike tour are only offered in the fall.

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.

See the Skyline from a Helicopter

Looking for a romantic activity in Chicago? If you are able to splurge one of the best ways to see the beautiful skyline is from a helicopter tour.

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.

WNDR After Dark

Visit the WNDR Museum, an immersive art and technology experience, for a special “WNDR After Dark” event where guests can enjoy a live DJ as they walk through the museum during extended hours. All ages are welcome. Alcohol will be available for purchase for guests 21+. Tickets to WNDR Museum must be purchased in advance at https://www.wndrmuseum.com/chicago/events.

Runs one Friday night a month.