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

Wondering what to do in Chicago at night? Below are the best things to do in Chicago at night.

Looking for fun things to do in Chicago tonight? The are tons of unique things you can do in Chicago at nighttime. If you are visiting Chicago in the summer, exploring the city after dark is more pleasant as you can avoid the strong sun and heat.

Best Things to do in Chicago at Night

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Below are the top things to do in Chicago in the evening.

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.


If you prefer to enjoy the same views over a meal or a drink, there is an upscale restaurant on the 95th floor named the The Signature Room at the 95th, and a bar on the 96th floor called The Signature Lounge at the 96th which are open late 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 Photos at The Bean

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Although The Bean is very very touristy, don’t skip it.  It is a great photo spot and a must on any Chicago bucket list.

Open daily to 9pm.

Have Fun at Navy Pier

Navy Pier can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants and bars. Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises. Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer.

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

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

skyline from lake cruise in Chicago in the summer
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. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.


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, typically from early May through mid-October, depending on weather.

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.

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 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.

Programming will resume in April, 2022

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. If your time is short, you can join these tours to see Chicago at night:


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:


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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.

See the Skyline from a Helicopter

If you are able to splurge one of the best ways to see the beautiful skyline is from a helicopter tour.

Play Indoor Mini Golf

Big Mini Putt Club (1302 N Milwaukee Ave, Chicago, IL 60622) is 9-hole indoor miniature golf course with a full bar serving craft cocktails, local draft beers, and other drinks in a fun, lively setting.

Open until 11:30pm Monday-Thursday, 1am Friday and Saturday and 11pm on Sundays.

Listen to Live Jazz at the Green Mill Cocktail Lounge

Listen to live jazz music at a historical Chicago spot. The Green Mill Cocktail Lounge 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.

Things to Do in Chicago in Night in the Summer

These nightly activities are only available in the summer.

Watch Free Fireworks

Navy Pier puts on a free fireworks show twice a week between Memorial Day and Labor Day. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars. Another great option for watching the fireworks is a lake cruise or river cruise which will stop on the water for passengers to enjoy the show.

Watch Free Movies in the Park

Every summer you can watch free movies in the evenings in Chicago’s public parks with the annual Movies in the Parks series. Movies in the Parks is part of Night Out in the Parks, which features more than 350 outdoor cultural & arts events in parks throughout the city in the summer.  Movies start at dusk. Click here to see the schedule.

Things to Do in Chicago in Night in the Winter

Go Outdoor Ice Skating

There are several places to go outdoor ice skating in Chicago in the evening.

The McCormick Tribune Ice Rink in Millennium Park (right in front of The Bean) is open daily until 9:00PM. Admission is free, but online ticketed reservations are required. Reservation dates are released 2 weeks in advance.

Skating ribbon at Maggie Daley Park in Chicago

The skating ribbon at Maggie Daley Park located next to Millennium Park is open daily to 10:00 pm. Reservations are strongly encouraged.

Go Sledding

If there is snow on the ground (usually at least 3 inches), you can go sledding even at night.
These sledding hills in Chicago have lighting and are staffed and open after dark when conditions allow:
Caldwell Woods
(W Devon Ave & N Nagle Ave, Chicago, IL 60646) – This forest preserve on the Northwest side is close to Superdawg one of the best hot dog places in Chicago. Call ahead at 847-647-2240 to make sure sledding hill and parking area are open.

Dan Ryan Woods Visitor Center (S Western Ave & W 87th St, Chicago, IL 60620) – This giant forest preserve in the Beverly neighborhood also features a separate area for snowboarding. Call ahead (773-233-3766) to check whether the hill and parking areas are open for sledding before heading out.

Open until 7:30pm Sunday – Thursday and 8:30pm Friday-Saturday.

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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