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.
No matter what time of year, there’s a game going on somewhere!
Be part of the Crosstown Classic, where Northsiders cheer on the Cubs at Wrigley Field and Southsiders root for the White Sox at U.S. Cellular Field.
Is 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?
6. Experience Live Music
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:
For more classical music, The Grant Park Music Festival is the nation’s only free outdoor music series of its kind, hosted at Millennium Park’s Jay Pritzker Pavilion every year!
7. Stay After Hours at a Museum
Many of the top museums in Chicago offer after-hours, adults-only events with cocktails, special tours, and smaller crowds at the exhibits.
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.
9. Laugh at a Comedy Show
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!
Don’t leave Chicago without going to a night show at Second City, iO, or Annoyance Theater, which all offer extremely affordable tickets!
You’re likely to recognize some celebrities, and may even catch them performing!
Escape rooms are one of the most popular forms of group entertainment and The Escape Game has great themed rooms: Special Ops, The Heist, Gold Rush, and Prison Break.
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!
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.
Nights Out In a Park
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.
One of the nation’s largest and most impressive libraries is located in downtown Chicago and is open until 9 pm.
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 are usually 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.
Free Music Mondays at Empty Bottle
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 the calendar of events at emptybottle.com.
Summer Festivals
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 a 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
Ice Skating in the Winter
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.
Head to Logan Square for Free Music, Comedy, or DJs
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.
Ed Paschke Art Center
The work of legendary Chicago painter Ed Paschke is preserved at this Jefferson Park art center, and is open until 7 pm 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.
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.
Acoustic Music at Coffeehouses
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!
Get Free Access to Popular Attractions
OK. Admittedly purchasing a tourist discount pass isn't free, in fact, these passes can seem expensive.
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.
FAMILY-FRIENDLY NIGHT ACTIVITIES
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.
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!
Spend the Night at Museum
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!
Family-Friendly Improv Comedy
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 8 pm Thursdays and Fridays, and 6 pm and 10 pm Saturdays.
ComedySportz 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!
See a Play
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.
Barrel of Monkey’s performs a family-friendly show called “That’s Weird Grandma” every Monday night that will get everyone to giggle.
If your kiddos are very young, try Emerald City Theatre Company or the Chicago Children’s Theatre.
Cosmic Bowling
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 1 am during the week, and 3 am on weekends.
With snacks and dinner options at Alley Dogs, the family can spend the whole evening eating and bowling under black lights!
Waveland Bowl 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.
Paint your Own Pottery
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!
Glazed Expressions 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!
Dinner at a Kid-Friendly Restaurant
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.
SafeHouse Chicago 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.
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.
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.
Navy Pier Centennial Wheel & Ride (hours vary by season)
Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
