BEST Things to do in Chicago at Night

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 (2026)

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.

Drunk Dracula

Step into a darkly enchanting adult-only adventure at Drunk Dracula where laughter, tipsy thrills, and the legend of Dracula collide. Each 90-minute session invites you to sip, shiver, and revel in the mischievous antics of a vampire gone delightfully rogue. Mingle with fellow thrill-seekers in a mysterious, adult-only setting. Must be 21+ with valid ID.

When: Through November 7, 2026

Where: 182 North Wabash Avenue, Chicago, IL 60601

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

Drunk Christmas Carol

Drunk Christmas Carol raises a glass to Dickens with chaos in the air. One haunted miser, three ghosts, and a whiskey-fueled retelling await. Step into Drunk Shakespeare Chicago as Dickens gets a boozy holiday shake-up. One actor takes five shots of whiskey, then joins an unruly retelling of A Christmas Carol while Scrooge meets three ghosts and the room waits to see whether he changes or gets totally scrooged.

When: Starts November 11, 2026

Where: 182 North Wabash Avenue, Chicago, IL 60601

Cost: Prices start at $49 per person. Click here to purchase tickets.

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:

Tribute to Dolly Parton
Tribute to Metallica
90s Unplugged
Tribute to Adele
The Best of Joe Hisaishi
Queen vs. ABBA
Tribute to Juan Gabriel on Strings

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

Cleopatra: The Immersive Exhibition

Cleopatra: The Immersive Exhibition invites you to step into the extraordinary world of Egypt’s Last Great Queen. Discover the story of her reign, power, love, lifestyle, and legacy as it comes to life with cutting-edge immersive storytelling and real artifacts.

When: Starts November 20, 2026

Where: EXP Rosemont, 9900 Berwyn Avenue, Rosemont, IL 60018

Cost: Prices vary. Early Bird price of 15% off tickets for a limited time only.

Smithsonian Starstruck: An Immersive Experience

Launching in Chicago, and created in collaboration with the Smithsonian Astrophysical Observatory, Smithsonian Starstruck: An Immersive Experience is a fully interactive, 3D virtual reality experience that takes visitors on a breathtaking journey through the cosmos, from dazzling galaxies to the edge of a black hole.

Where: 108 West Germania Place, Chicago, IL 60610

Cost: Prices vary. Click here to purchase tickets.

Serial Killer: The Exhibition World Tour

Serial Killer: The Exhibition World Tour is a gripping, immersive true-crime experience featuring the world’s first and only collection of authentic artifacts connected to history’s most notorious serial killers. Following its massive success in London, Paris, and Berlin, and fresh off its U.S. premiere in Atlanta, Chicago is officially the second stop of this blockbuster American tour. Built on ten years of research and collaboration with over sixty global collectors, this expanded landmark exhibition features over 2,100 authentic artifacts while introducing exclusive Chicago content exploring the city’s dark criminal history, including dedicated sections on H.H. Holmes and John Wayne Gacy. Recommended for ages 14+ (not suitable for sensitive audiences).

Where: Cinespace Chicago Film Studios, 2428 W 15th St, Chicago, IL 60608

Cost: Prices vary. Click here to purchase tickets.

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.

Take a Lake Cruise

If you enjoy being on the water, a lake cruise is one of the best summer activities in Chicago. Summer is the best season for a lake cruise as the cool breeze on the water is refreshing on a very hot day. While you don’t get to see the buildings up close like you would on a architecture river cruise, you do get to enjoy amazing skyline views especially around sunset. Lake cruises depart from both Navy Pier or the Michigan Avenue Bridge (DuSable Bridge).

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

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 Flyover, an immersive flying theatre experience.

Open to 8pm Sunday-Thursdays and 9pm on Fridays & 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 11pm 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.

8:30-9:00pm on Thursdays through Sundays

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.

Watch Free Movies Outside

There are several places you can watch free outdoor movies in Chicago during the warmer months including Gallagher Way in Wrigleyville and various Chicago public parks.

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.

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.

6pm & 8:30pm 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

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.

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.