This post lists the things to do in Chicago, updated for 2020, including free, family-friendly, as well as seasonal attractions and activities.
Check out our Chicago Visitors Guide, with budget advice, travel guides, and information about local Chicago attractions.
Below are our top 10 recommendations for things to do at night in Chicago. Some of the items here would also fit in the other sections.
Within each listing, we provide links for a more in-depth exploration of each selection.
Several of the items below are already included for free with the purchase of a tourist discount pass.
Ghost tours, a stroll on the Riverwalk, and architecture cruises on the Chicago River are just some of the great nighttime tours that you could take.
Free Tours By Foot offers this pay what you like walking tour seasonally, so check out the calendar and see what other tours we have!
If we don’t offer an evening guided tour, our self guided and audio tours can be taken at any time.
The Chicago Theatre District offers a variety of live performances at renowned venues.
The Chicago Theatre presents top-billing shows and concerts.
Here are a few other theatres you might want to consider while in Chicago:
In the mood for dining and a show? Check out Tommy Gun’s Garage Dinner and Show to be transported back to the roaring 20s.
Tip: On a budget and looking to save on ticket prices? Groupon offers discounts on the hottest shows in town!
The Goodman offers half-price tickets in the mezzanine day of the performance! All discounts subject to availability.
See the Chicago skyline from a birds-eye view and marvel at the architecture as the city lights up.
The main Observation Decks in Chicago are:
All three are included for free on at least a few of the tourist discount passes.
If you aren’t sure which of the three to visit, we’ve put together a list of the pros and cons of each of them.
There are several tour companies in the Chicago area that offer cruises throughout and around the city.
Some of these cruises are held after dark or at sunset, allowing you to see the city skyline from a unique perspective as all the buildings begin to light up the night sky.
There are also dinner cruises available which include either a 3-course meal or a buffet, music, dancing, and of course a cruise after dark.
For more details about this activity, please check our post covering Chicago Boat Tours & Cruises.
No matter what time of year, there’s a game going on somewhere!
Baseball not in season? The Blackhawks hit the ice at the United Center fighting for another Stanley Cup!
And who can deny a chance to see the Chicago Bears play at Soldier Field?
There are endless choices for live music in a city as large as Chicago, from local bands at hundreds of bars and restaurants to the Chicago Symphony Orchestra, one of the most renowned symphonies in the world.
You can also see concerts from some of the biggest names in the music industry at some of the following venues:
Many of the top museums in Chicago offer after-hours, adults-only events with cocktails, special tours, and smaller crowds at the exhibits.
What else should you do when visiting a new city? If nothing else, make sure you try some of the famous Chicago Style Deep Dish Pizza.
But, if you’re still hungry, sample your way with these self-guided food tours of Chicago neighborhoods that can be taken day or night.
Or if you’re looking for something a little stronger…
In our Guide to Chicago Bars you can find out about historic bars, game bars, and where to have a pint while playing some trivia.
If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.
The Windy City is famous for generating some of the biggest legends of comedy: Steve Carell, Jim Belushi, Steven Colbert, Tina Fey, Amy Poehler, Bill Murray…the list goes on!
You’re likely to recognize some celebrities, and may even catch them performing!
No, really! The Chicago Riverwalk is a hidden gem of Chicago Downtown.
Open 24 hours, you can stroll along six blocks of a continuously landscaped path along the Chicago River any time of night.
From State Street to Lake Street, each block has its own identity, separated by overhead bridges.
If you want a romantic spot to take in the twinkling city, you’ll find it at the Riverwalk!
Join us from April through October on our free Chicago Riverwalk Tour.
Play the Escape Game
You and your friends or family must work together to find clues and solve puzzles in a set amount of time. If you succeed, you get the ‘keys’ to get out of the room.
If you fail, well, they still let you out and you will have had a great experience! Better still, The Escape Game experience is included in some tourist passes like the Chicago GoCity Card.
Many of the activities included above in our top 10 section are free, such as walking down the Magnificent Mile or taking a free walking tour. But there is so much more!
Be sure to read our posts on free things to do, both of which include items that are free.
Below are some suggestions on how to spend your evening in Chicago for free.
Wherever you might be in the city, you are not far from a local park that is hosting a neighborhood event.
Chicago holds over 2000 unique events at 77 different neighborhood parks throughout the year, and many are free.
You may find a movie showing, a community bonfire, a seasonally-themed party for the whole family, and even a service project.
Info: For the schedule of events, go to www.chicagoparkdistrict.com/night-out-in-the-parks
One of the nation’s largest and most impressive libraries is located in downtown Chicago and open until 9pm.
Be sure to take in the architecture on the outside and inside of the building, as well as the glass roof of the Winter Garden on the 9th floor.
You can also create some art for free in the Maker Lab on the 3rd floor, and there is usually a free art exhibits for the adults and storytimes in the Children’s Library.
Info: Harold Washington Library is located at 400 S. State St. Check out www.chipublib.org/locations/34/ for events and visitor info.
One of Chicago’s top locations for indie music is the Empty Bottle, located in the Ukrainian Village neighborhood.
There is music every night of the week, and Monday nights are usually free, featuring local and national musical acts.
Info: Empty Bottle is located at 1035 N Western Ave, see calendar of events at emptybottle.com.
Chicago is famous for its free summer festivals. Throughout the summer, you can find the House Music Festival, Gospel Fest, Blues Fest, the Taste of Chicago, Jazz Fest, and World Music Festival.
Music goes well into the night and features some of the top acts in each genre, taking place on the biggest outdoor stages in downtown Chicago.
On the smaller scale, most of Chicago’s neighborhoods host a local street festival throughout the warmer months, some of which are free admission.
Info: www.cityofchicago.org/ for details about upcoming summer events and festivals throughout the city
From mid-November to mid-March, whenever the weather permits, Millennium Park hosts the McCormick Tribune Ice Rink, free and open to the public.
If you bring your own skates, you won’t have to spend a dime to skate outdoors, well into the night in the beautiful downtown under the lights.
The Logan Square neighborhood is a trendy scene for nightlife, and two bars in particular have no-cover events almost nightly.
Cole’s Bar is always free and hosts comedy, DJs, and live music.
Just down the street is the Whistler, which also hosts DJs and music that often caters to the jazz crowd.
Info: Cole’s Bar is located at 2338 N Milwaukee Ave. Visit www.colesbarchicago.com for more details. The Whistler is located at 2421 N Milwaukee Ave. Visit whistlerchicago.com for more.
The work of legendary Chicago painter Ed Paschke is preserved at this Jefferson Park art center, and is open until 7pm every night.
Visitors can take either a staff-led tour or can check out an iPod and take a self-guided tour of the gallery.
You can find works from every period of Paschke’s artistic career, and even a re-creation of his Howard Street studio including unfinished works of art left after his death in 2004.
Info: The gallery is located at 5415 W Higgins. Details can be found at http://www.edpaschkeartcenter.org/
Bookstores, libraries, and cafes in Chicago often host a number of literary events.
Book release parties, book readings, and author readings with local (and even nationally-known) writers are great ways to get to know an author or literary work in an intimate setting.
One unique bookstore to check out is City Lit Books in Logan Square, which hosts these events plus open mic nights.
Info: City Lit Books can be found at 2523 N Kedzie Blvd, and details are at www.citylitbooks.com.
If you would rather hear music at quieter volumes, many of Chicago’s cafes and coffee shops have acoustic music performed live in the evenings.
Whether it is a small jazz trio or a singer-songwriter with an acoustic guitar, you can discover new local talent almost every night in Chicago.
Check out the coffee and wine bar Drunken Bean for a relaxing atmosphere of jazz, or Café Mustache for an eclectic mix of beats, karaoke, and live music.
There is so much architecture and unique landscape to see downtown.
The Bean and nearby Crown Fountain in Millennium Park may be the most well-known attraction, and you can also stroll through Lurie Garden and Maggie Daley Park.
Head south a few blocks and visit one of the world’s largest fountains, Buckingham Fountain, in Grant Park.
If you are at or near Navy Pier, you can also enjoy a fireworks display every Wednesday and Saturday night all throughout the summer, and right on the lake!
OK. Admittedly purchasing a tourist discount pass isn’t free, in fact, these passes can seem expensive.
However, the all-inclusive tourist passes include most of the city’s popular tourist attractions and tours, including hop-on-hop-off bus tours and boat cruises.
In fact, they usually offer over 80 options to choose from.
The object of these all-inclusive passes is to experience as many things in a day as you have time for.
These passes are sold in increments of days, and the longer the pass the less the daily cost is.
So, if you plan efficiently, you will end up getting free access to several tours and attractions.
Many suggestions already made in the previous sections are appropriate for families, but there are lots more fun things for kids in Chicago at night.
Many of these attractions are conveniently located in the Loop and are perfect for families and, at the same time, great for night owls.
For family-friendly ideas at any time of the day, check out our guide on things to do with kids in Chicago.
The Blue Man Group mixes music, humor, and technology to create an electric experience that has captured audiences of all ages worldwide for over 25 years!
Conveniently located at the Briar Street Theatre at 3313 N. Halsted, you and your family/friends can have a wild night you’ll never forget!
Tip: Book early and reserve the Splash Zone seats. Get ready to be covered in neon colors as the group sends paint splattering out of one-of-a-kind instruments while you and your friends dance and shout!
Many of the museums offer special events where the kids can spend the night amongst the exhibits – whether it is dinosaurs or butterflies depends on the museum.
They offer kid-friendly activities and tours of the museums and an unforgettable way to experience some of the iconic sites of Chicago.
Escape rooms have become very popular group activities recently.
Guests enter into pulse-pounding environments and will work together to find clues to escape the room within a certain period of time.
Room Escape Adventures
410 S. Michigan Ave
Closest L stop: State/Van Buren Brown Line
Recommended ages 8 and up
Games at Room Escape Adventures include escaping a room with a zombie, and cracking a code on New Year’s Eve 1999 before Y2K hits!
Tip: Book your spots at their website, and Free Tours By Foot customers can enter the code FREEFOOT for $5 off their booking!
Chicago is a popular destination for comedy lovers, and it is double the fun when the comedy is made up on the spot!
One of Chicago’s top improv comedy options is ComedySportz, in which two comedy teams “compete” for laughs, encouraging the audience’s participation and suggestions.
The comedy is safe for the whole family; in fact, the comedy teams are penalized in their competition if they accidentally say anything naughty!
Shows are 8pm Thursdays and Fridays, and 6pm and 10pm Saturdays.
929 W. Belmont Ave
Closest L stop: Belmont Red/Brown line
All Ages Welcome
Tip: the comedians will ask for suggestions from the audience before most skits; be ready to shout out something that will make their next skit crazy!
There are many touring shows in and out of Chicago through Broadway in Chicago or a Hot Tix Booth.
You never know when there will be a hit musical or family-friendly show! There are a few fantastic local shows that are consistently here in Chicago.
Bowling is always a great option for a family outing, and it is even more fun when the alley goes dark!
When a bowling alley goes “cosmic”, the lights go down, black lights glow, and the music gets everyone dancing in between their turns.
Waveland Bowl has cosmic bowling every night Thursday-Monday at different hours. The alley is open until 1am during the week, and 3am on weekends.
With snacks and dinner options at Alley Dogs, the family can spent the whole evening eating and bowling under black lights!
3700 N. Western Ave
Closest L stop: Addison Brown Line
All Ages Welcome
Check out this Yelp review from one recent guest: “Love this Chicago institution! Love the staff, the owners, the facilities. The location is great too.”
Tip: Save money on the kids’ admission by registering at kidsbowlfree.com, and kids 14 and under bowl two games free! This is good from May 1 through October 1.
Young artists will love the opportunity to paint and decorate a piece of pottery.
At Glazed Expressions in Lincoln Park kids and adults can select pottery to paint and explore their artistic sides until their work is perfect for them!
Stop by after taking our Lincoln Park walking tour.
717 W. Armitage Ave
Closest L stop: Armitage Brown Line
Painters of All Ages (who are careful with breakable pottery) are welcome
Tip: Your artwork will not be ready to take home that night! It will be glazed and heated in the kiln after you are finished.
It will be ready to be picked up after 7 days, and you must pick it up after a week, but before a month later. Plan accordingly!
Chicago needs no introduction when it comes to food, and some restaurants have created an entire experience for the whole family.
A fun option for the entire night is SafeHouse Chicago, a spy-themed restaurant that lets kids explore secret passageways while they are waiting for their food.
After dinner, another popular escape room, EscapeHouse Chicago, is right next door, with 2 experiences to choose from: escaping the White House, or escaping the Safe House.
60 E. Ontario St.
Closest L stop: Grand/State Red line
EscapeHouse recommends ages 14 and up, but younger children can participate
Tip: Spend the whole afternoon and evening on the Mag Mile! Book our Magnificent Mile walking tour for the afternoon, and then enjoy some shopping, prior to dinner and the escape room at night.
Enjoy a Musical performance
There are a lot of options to see and hear some live music in Chicago.
If you want to bring the kids out in the evening, the Old Town School of Folk Music is kid-friendly, as it is also a music education center.
It has concerts that have reasonable start times. Be on the lookout for Kid Concerts and the frequent Teen Open Mic nights!
Old Town School of Folk Music
4544 N. Lincoln Ave
Closest L stop: Western Brown Line
Recommended ages 12 and up, all ages for Kid Concerts
There is not a bad seat in the house.
Watch Loyola Basketball
Everyone knows about Chicago’s major sports teams: the Bears, Bulls, Cubs, White Sox, and Blackhawks.
Why not try a different atmosphere? This is a budget-friendly experience!
The Loyola University Ramblers basketball men’s and women’s teams are sure to make Gentile Arena on the city’s far north side an exciting place to be this upcoming season.
Loyola Ramblers basketball
Gentile Arena 6525 N. Sheridan Ave
Closest L stop: Loyola Red Line
School spirit is sure to be at an all-time high! Purchase tickets for upcoming games through the Loyola Ramblers website for games that begin in November.
Family Fun at Navy Pier
No list of evening activities for the whole family would be complete without highlighting Navy Pier.
One of the most visible images along Chicago’s lakeshore is the Centennial Wheel, a giant Ferris wheel in Pier Park that gives an incredible view of the city- especially with the glittering lights at night.
Navy Pier hosts the Chicago Children’s Museum, which has extended hours on Thursdays, open until 8 pm, and is free admission from 5-8 pm.
And finally, the entire family can enjoy a movie at the IMAX or a show at the Chicago Shakespeare Theater.
During the summertime- stick around for the fireworks that are on Wednesdays and Saturdays.
Tip: Admission into Navy Pier is free; each ride will require paid tickets. Parking can be pricey, so be on the lookout for the seasonally-operated Free Navy Pier Trolley Service, which stops at the Grand/State Red Line stop.
As we mentioned above in the FREE section, getting a tourist attraction discount pass can save you considerable money, especially when it comes to night activities.
Be sure to read our post comparing the different tourist discount passes.
All passes include night attractions and activities, though some passes have more than others.
In general, tourist passes include at least a few, if not nearly all, of these Top Ten nighttime attractions that stay open daily until at least 9 or 10 pm, if not later.
To find out about tourist passes and to decide if buying one is right for you, see our post, Chicago Attraction Passes: Which One Is the Best to Buy.