As someone from the San Francisco Bay Area (a place that’s no slouch when it comes to nightlife), I thought I had a pretty good grasp on what a city could offer once the sun goes down.
But Chicago? Chicago blew me away. I’m talking blew-SF-out-of-the-water level impressed.
Sure, you’ll have no problem filling your days here — snapping pics at The Bean, devouring deep-dish pizza, hitting up iconic museums — but the real magic kicks in after dark. The city transforms, for the better!
You’ve got rooftop lounges with skyline views, jazz clubs tucked behind secret doors, world-class museums that play host to 21+ evening events, and immersive theater experiences that pop up all over the city.
Here are some of the most unique things to do in Chicago at night — from low-key hangs to unforgettable late-night adventures.
This post may contain affiliate links. You won’t be paying a cent more, but in the event of a sale, the small affiliate commission I receive will help keep this blog running/pumping out useful and free content. Thanks a lot!
Table of Contents
CHICAGO IN A NUTSHELL
Here’s a quick overview of all the useful info you need to plan an awesome trip!
When To Go: During the late spring, early summer, and early fall months: May, June, September, and October. Summers can be very hot and humid, but you’ll find plenty of outdoor events and festivals during this time.
Where To Stay: Near the center of all the action is best! I recommend The Westin Chicago River North or Pendry Chicago for more luxe vibes; Virgin Hotels Chicago for hip boutique hotel vibes at an affordable price!
Nearest Airport: O’Hare International Airport (ORD)
How to Get Around: Chicago is well-known for its convenient public transit system. It’s also a very walkable city! For longer distances, opt for rideshare before choosing to rent a car. Parking in downtown Chicago can be difficult and expensive — many hotels charge a daily fee for parking, and street parking can be limited and expensive.
Must-Do’s: See The Bean (Cloud Gate) at Millennium Park, take an architecture boat tour, visit Navy Pier, try a Chicago-style hotdog, and get a deep-dish pizza at Pequod’s (I recommend the spinach and garlic).
Before You Go: Pick up Go City’s Chicago Attraction Pass if you plan on sightseeing and going into museums. It’ll save you so much money on attraction tickets!
WHAT IS CHICAGO KNOWN FOR?
If you know nothing about Chicago, let’s start with the basics. Chicago is the third most populated city in the United States. It is a Midwest city that sits adjacent to Lake Michigan and is famed for its architecture.
Chicago is best known for the following:
- The Bean, which is officially known as Cloud Gate at Millennium Park
- Impressive architecture and skyscrapers
- Chicago deep-dish pizza
- Chicago-style hot dogs
- Navy Pier, one of Chicago’s most iconic landmarks
- Wrigley Field, home to the Chicago Cubs
- The Chicago Riverwalk, a pedestrian area lining the Chicago River
30 BEST THINGS TO DO IN CHICAGO AT NIGHT
Now that you have the download on Chicago’s most iconic attractions and features, let’s dive into the best things to do in Chicago at night!
1. SEE THE CITYSCAPE FROM ABOVE

Time to enjoy some quintessential cityscape views at a staple Chicago landmark! Chicago is one of the best places (if not the best place) in the USA to enjoy cityscape views. And nighttime is one of the best times to view the city’s twinkling lights from above!
The two most popular observation decks in Chicago are:
- SkyDeck Chicago – Located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower)
- CHICAGO 360 – From the top, you’ll be able to see Lake Michigan, Navy Pier, Soldier Field, and the Magnificent Mile.
Both feature spectacular views of Chicago’s skyline!
TWE RECOMMENDED
Save with Go City’s Chicago All-Inclusive Pass
Save up to 51% on tickets to Chicago’s most popular attractions, including Shedd Aquarium, CHICAGO 360, Skydeck Chicago, Shoreline Architecture River Cruise, Museum of Science and Industry, and more. You can choose from 25+ different attractions in total.
We explored Chicago with this pass and got to see a lot more than we usually do in big cities — while saving a ton of money!
Pro Tip: Don’t want to pay for views? For similar skyline views, head to The Signature Room at the 95th. This restaurant/lounge offers guests a dining experience with sweeping 360-degree views. All you have to do is pay for your meal or drinks!
2. SEE A LIVE PERFORMANCE

If you’re into Broadway shows, plays, and productions, Chicago’s got an entire area that’s made for just that. The Chicago Theatre District offers a variety of top-billing performances and concerts held across many renowned venues.
Take, for example, The Goodman Theatre. This venue is the largest and oldest non-profit theatre in Chicago, and if you find a show you like there, we highly recommend booking tickets!
Pro Tip: Looking to save on ticket costs? At 10 am each performance day, remaining mezzanine seats at The Goodman are available at half-price online!
Here are a few other theatres you might want to check the events calendar for:
3. TAKE A SUNSET RIVER CRUISE

Architecture river cruises in Chicago are an absolute must!
Not only will taking a river cruise help you get your bearings and help you better understand the layout of the city, but you’ll also learn so much about the city’s inspiring past (and learn about all the crazy stuff they did to prepare for the 1893 World’s Fair).
And did we mention that you’ll be an architecture pro after your cruise? Trust us, they are a lot of fun.
While most people opt for the daytime river cruise, evening river cruises are even more picturesque. You’ll get the added perk of seeing the city skyline lit up, from a really unique perspective!
4. TAKE THE GANGSTERS AND GHOST TOUR
Want to learn about Chicago’s dark past? With a historian as your guide on the Gangsters and Ghosts Tour, you’ll step back to the roaring 20s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone.
Not only will you get to hear about the wild stories of the past, but you’ll also visit previous gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
In our opinion, this is one of the most fun things to do in Chicago at night! This historic tour is a walking tour so be prepared to walk.
5. TAKE THE CHICAGO NIGHT CRIMES BUS TOUR
It’s no secret that Chicago has a colorful history related to crime. If you’re intrigued by all the crime history that’s tied to the city, then the Chicago Night Crimes Bus Tour is for you.
On this 2.5-hour tour, you’ll hop on a bus to discover the ‘dark side’ of the Windy City. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you learn about things like the St. Valentine’s Day Massacre and ‘The Enforcer’s Safe’ and stop by local watering holes.
In addition to learning about a super intriguing topic, you can expect your guide to be funny, informative, and engaging!
6. VISIT A MUSEUM AFTER HOURS

When a museum closes for the day, they don’t really always stay closed. Many of the top museums in Chicago offer adults-only after-hours events that run until 10pm!
These events are usually themed differently each week, featuring nighttime cocktails, tours, and special exhibits. Some even include dancing or game nights!
Here are just a few examples:
- Adler After Dark
- Art Institute After Dark
- Museum of Science and Industry After Hours
- Museum of Contemporary Art Prime Time
- Shedd After Hours
- Chicago History Museum Happy Hour
TWE RECOMMENDED
Save with Go City’s Chicago All-Inclusive Pass
Save up to 51% on Chicago’s most popular attractions, including Shedd Aquarium, CHICAGO 360, Skydeck Chicago, Shoreline Architecture River Cruise, Museum of Science and Industry, and more. You can choose from 25+ different attractions in total.
We explored Chicago with this pass and got to see a lot more than we usually do in big cities — while saving a ton of money!
7. DO THE CHICAGO RIVERWALK

Open 24/7, the Chicago Riverwalk is a really enjoyable activity in Chicago at night. Since it’s only about 1.25 miles, you can enjoy a peaceful, flat stroll along a beautifully manicured path along the Chicago River.
Grab a bite to eat at one of the many cafes, bistros, and restaurants that line the water. Stop for drinks or even for some souvenir shopping along the way!
8. SEE THE NAVY PIER FIREWORKS

Navy Pier stretches more than six city blocks and offers incredible views of the Chicago skyline, parks and Lake Michigan. One of the best things to do at Navy Pier is just to take a stroll through the whole thing!
If you happen to be traveling in the summertime, Navy Pier is not to be missed. There is a fireworks show that takes place on Wednesday and Saturday nights from Memorial Day weekend through Labor Day weekend.
Secondly, if you’re visiting Chicago during the holiday season, don’t miss Navy Pier’s holiday event, Light Up the Lake. This holiday event runs from late November to early January.
At the event, you can expect massive light sculptures, an ice rink, an authentic holiday beer garden, kiddie train rides, a gift market, and other family-friendly and date-night activities!
While there is no admission fee to enter Navy Pier, some of the rides and attractions within Navy Pier do cost extra. For example, the Ferris wheel costs $15 for adults. There are also other ride passes for sale.
Want to see the fireworks from the water on your own private boat? Check out this 2-hour boating excursion and enjoy the private sail ending with The Navy Pier Fireworks.
9. LINCOLN PARK ZOO
Similar to the museum after-hours events, the Lincoln Park Zoo also has its own adults-only program after dark!
Throughout the year, the Lincoln Park Zoo is open late on some Friday nights (during the summer, holidays, and other special events) for adults-only events that offer alcohol. These events typically include unique animal chats, educational entertainment, a live DJ, and multiple bars throughout the zoo.
While the zoo is normally free, tickets for nighttime events are usually required. Check their calendar for the latest nighttime events.
10. CATCH A COMEDY SHOW

You will easily find comedy shows dotted all throughout the city of Chicago. If you’re looking for a festive night out filled with laughter, you definitely can’t miss a comedy show in the city.
If you’re looking for pointers, on where to go, check out Laugh Factory Chicago, where you can enjoy laughs and cocktails 6 nights a week.
Second City, The Comedy Bar, and Annoyance Theater are all other great options that sell affordable tickets!
The comics will range from local headliners to up-and-comers to well-known comedy stars–and you never know, but celebrities tend to drop in for surprise performances a lot!
11. GO TO AN ICONIC JAZZ CLUB

Step back in time and visit one of the oldest clubs in the US! Green Mill is a classic Chicago establishment known for its jazzy live music and poetry performances, along with its connections to Chicago mob history (Al Capone used to frequent this spot back in the day).
Even today, you’ll still find this place maintaining its old-timey atmosphere, with jazz music straight from the 1930s and 1940s. It’s quite an authentic experience, meaning it can get crowded, smoky, and loud. But what’s not to love about that?
Pro Tip: Depending on the night you go, there could be a small cover charge for the nighttime jazz. It definitely gets busy, so we recommend getting there early as they do not take reservations. The place usually fills up before 11pm.
12. VISIT A SPEAKEASY OR ROOFTOP BAR
Chicago has its fair share of speakeasies, given its mobster history. It might take a little extra work to track down these “secret” Chicago bars, but once you find them, they’re so completely worth it!
Local favorites include Blind Barber in Fulton Market (fun bar behind an actual barbershop), Bordel in Wicker Park (craft cocktails and cabaret), Violet Hour in Wicker Park, and Chicago Magic Lounge in Andersonville.
In addition to the many speakeasies you can visit, be sure to check out a rooftop bar or two during the warmer seasons. Cabra, Rooftop at Nobu, Cabana Club, Cindy’s Rooftop, and Z Bar are all great options for good drinks and views!
13. DO AN ESCAPE ROOM WITH YOUR FRIENDS

Escape rooms have exploded in popularity these days. They make for some of the best indoor entertainment for groups, and one of the best features about them is the fact that they are open late.
One perk of being in a big city like Chicago? The sheer number of escape room brands to choose from.
Whether you’re into heist scenarios, haunted mansions, prison breaks, or sci-fi missions, Chicago’s escape room scene has you covered—with many companies winning national awards for story design, production value, and immersive special effects.
If you and your group are willing to flex those brain muscles, you should def test your out-of-the-box thinking in an escape room!
The Escape Game, one of the more popular chains, is included in some tourist passes like the Go City Chicago Attraction Pass.
👉 Pro Tip: We like to check Groupon before booking direct—almost every time we’ve done an escape room in Chicago, we’ve found deals for 30–40% off the regular price. Explore the escape room deals here.
14. GO DANCING AT A NIGHTCLUB

There is no shortage of nightclubs in Chicago for dancing the night away. A lot of these nightclubs not only feature energetic dancefloors but also spinning DJs and bottle service if that’s how you want to roll!
Depending on which neighborhood you’re staying in, you’ll want to check out the following:
- Smart Bar (Wrigleyville)
- Tao Chicago (River North)
- Electric Hotel (River North)
- Sound-Bar (River North)
- Disco (River North)
- PRYSM Nightclub (Lincoln Park)
- Beauty Bar (Chicago West)
- Le Nocturne (Uptown)
15. GO BAR HOPPING

Just as there is no shortage of nightclubs or speakeasies, there also is no shortage of bars in Chicago. One of the best times to visit these bars is after nightfall when the atmosphere picks up and the liveliness is at its peak!
For cool, hipster bars, check out Sparrow in the Near North Side area, Debonaire in Wicker Park, or Emporium Arcade Bar (has locations in Logan Square, Wicker Park, the Fulton Market District).
For brewery hopping, don’t miss Revolution Brewing in Logan Square, Goose Island in Lincoln Park, or Half Acre in Lincoln Square.
And when you’re done barhopping, end your night with a few Chicago-style hot dogs or a pan of late-night deep-dish pizza!
16. VISIT A KARAOKE BAR

For the ultimate judgment-free nighttime activity in Chicago, hit up a karaoke bar! Karaoke bars in Chicago come in all shapes and sizes, from dive bars where you perform in front of others to more intimate settings where you can sing in the comfort of your own karaoke room.
Alice’s Lounge, Trader Todd’s, and Brando’s Speakeasy will be great options if you want to belt out tunes in public, while Sakura Karaoke Lounge in Chinatown is the one if you’re looking to rent a private room.
If you want to switch between bowling, playing arcade games, and karaoke-ing, head straight for Punch Bowl Social (they offer 2 small, private karaoke rooms for rent by the hour).
17. ATTEND A SPORTING EVENT OR CONCERT

Because Chicago is a major metropolitan city, a lot of artists tend to do shows here. Aside from big stadium shows, popular music venues in Chicago include House Of Blues, The Empty Bottle, The Green Mill Cocktail Lounge, and Smartbar. You can do a quick Google search for ‘events in Chicago’ and usually the music events will pop up at the top of your search results.
And of course, Chicago is home to the Chicago Cubs! If you’re a baseball fan, catching a game at Wrigley Field is one of the most iconic things to do in Chicago. You can also catch a Chicago Bears football game at Soldier Field.
Since there won’t be a show or sporting event guaranteed every night, you will have to do some research while planning your trip for your best chances at catching a concert or game!
18. VISIT THE ADLER PLANETARIUM
Enjoy a live, guided tour of Chicago’s night sky in Chicago’s oldest planetarium! Every month, the Adler Planetarium hosts an after-hours event for adults 21+, inviting them to explore the Museum Campus while enjoying themed drinks and live entertainment.
Usually, the drinking is paired with music and featured vendors, all while guests learn about space, the future of deep space exploration, and a featured topic of the month.
With after-hours admission, you’ll get full access to museum exhibits and galleries, unlimited sky shows in their state-of-the-art theaters, access to special guest lectures, and hands-on educational activities.
19. SEE A DINNER AND MAGIC SHOW

In the mood for dinner, comedy, and a magic show? Then you’ll need to prioritize a visit to Chicago Magic Lounge, a true hidden gem in Chicago! This wonderful venue is dedicated to bringing back the classic magic-bar scene in Chicago.
There’s a lot that happens when you reserve a seat at the Chicago Magic Lounge. The first hour is for food, cocktails, and magic of course! The second hour is dedicated to enjoying the opening act and main act. The magic will be impressive, and you can expect acts to include fun card tricks, hypnotizing, and mind-reading.
If you want to get a good laugh in and have a very entertaining night, definitely do not miss this one!
20. TAKE A HISTORICAL GHOST TOUR

Embark on a ghost-themed walking tour through Northside Chicago! On the Ghosts of Lincoln Park Walking Tour, you’ll visit some of the city’s most chilling locations and learn about the ghosts of gangsters and serial killers who haunt the streets.
This one probably sounds more terrifying than it really is, but one thing is for sure–you will sure learn a lot about Chicago’s crime history!
21. ARGYLE NIGHT MARKET
Since 2013, the Argyle Night Market has been keeping locals entertained with music, culture and food!
This seasonal event is held on Thursdays from June to September and features a variety of food trucks, local vendors, and live entertainment. Visitors can enjoy street foods from around the world, shop for handmade goods, and listen to live music.
The market also has a beer garden, where visitors can relax with a cold drink in hand while enjoying the warm summer night. After a two-year hiatus due to the pandemic, it’s finally back!
The Argyle Night Market is free to enter.
22. EXPERIENCE THE CHICAGO SYMPHONY ORCHESTRA

A night out listening to the Chicago Symphony Orchestra is a perfect activity for music lovers in Chicago. The Chicago Symphony Orchestra is EASILY one of the best orchestras in the world, and their performances are renowned for their exceptional quality and artistry.
The Orchestra performs at Orchestra Hall, which is a beautiful venue with excellent acoustics. The building itself is an architectural masterpiece, with Art Deco design elements and a grand entrance that sets the tone for an unforgettable evening.
If you attend a performance, expect a truly immersive experience that engages all of the senses! We’re talking powerful and moving music where the Orchestra’s world-class musicians bring each piece to life with their skill and passion.
23. VISIT BUCKINGHAM FOUNTAIN IN GRANT PARK

As one of the largest fountains in the world, the water action that Buckingham Fountain produces from early May to mid-October (when temperatures are above freezing) is a must-see.
Every 20 minutes until 11:00 PM, the fountain puts on an amazing water display that is free of charge to watch.
At dusk, the fountain show is especially nice! Lights and music accompany the 150 feet water jets, making it a must-do if you’re even remotely in the area.
In addition to the fountain itself, Grant Park is a beautiful and expansive green space that offers a variety of activities for visitors. The park is known as “Chicago’s Front Yard” and is home to many iconic landmarks, including the Art Institute of Chicago, Millennium Park, and the Museum Campus. Visitors can take a leisurely walk through the park either before or after the fountain show and enjoy the beautiful scenery!
If you’re looking for something to eat or drink, there are plenty of options in the area. The nearby neighborhoods of South Loop and Printer’s Row offer a variety of restaurants, cafes, and bars that cater to a range of tastes and budgets.
24. PLAY A ROUND OF GOLF AT TOPGOLF CHICAGO

Topgolf Chicago is a fun and unique activity to enjoy in Chicago at night — no matter if you’re traveling solo or with a large group. Located slightly out of the way in Schaumburg, Topgolf is a golfing range with a twist.
Instead of hitting balls into a traditional range, players aim for targets that are spread out across the range. Players score points based on how close they get to the targets, making for a fun and competitive experience.
Topgolf Chicago is open late, making it a great option for a night out. The venue is open until 11pm on weekdays and midnight on weekends.
In addition to the driving range, Topgolf also features a full-service restaurant and bar, making it a great spot to grab a drink or a bite to eat while enjoying the game.
25. GO ICE SKATING IN THE WINTER
If you’re visiting Chicago in the winter, one of the most fun things to do at night is to enjoy one of Chicago’s many seasonal ice skating rinks.
During the winter season, the city has several outdoor ice skating rinks that are open during the winter months, providing a fun and festive atmosphere for visitors and locals alike. A few to check out include:
- The McCormick Tribune Ice Rink in Millennium Park – Located in the heart of downtown, this rink is surrounded by cool architecture and offers beautiful views of the city skyline. The rink is typically open from mid-November to mid-March and offers free admission.
- Maggie Daley Park Skating Ribbon – This unique rink is shaped like a winding ribbon and offers a fun and challenging skating experience. The rink is open from mid-November to mid-March and offers skate rentals for a fee.
- Lincoln Park Zoo – The zoo also offers an ice skating rink during the winter months. The rink is located in the zoo’s Farm-in-the-Zoo area and is open from late November to late February.
26. ATTEND AN INTIMATE CANDLELIGHT CONCERT
Candlelight Concerts is a series of special classical music concerts that take place in beautiful, intimate venues bathed in candlelight. Chicago is home to a bunch of them!
Previous offerings include all sorts of themes such as “A Tribute To Taylor Swift”, “The Best of Hans Zimmer”, “Bach to The Beatles”, “A Tribute To Adele”, and so much more. Some of our favorites? The Halloween-themed specials!
If you see a themed show you like, you’ll want to book as soon as possible, as there are limited tickets available for Candlelight shows.
Click here to see all the candlelight concerts offered at this moment.
27. EXPERIENCE A DRUNK SHAKESPEARE SHOW
Looking for a unique and hilarious way to watch Shakespeare? Then get tickets to Drunk Shakespeare Chicago!
This magical stage where great things happen is set in a hidden speakeasy located behind the Chicago Theater. Guests enter to find a glam cocktail bar and library with over 10,000 books.
Five classically-trained actors meet as members of “The Drunk Shakespeare Society”. One of them has AT LEAST five shots of whiskey, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Hilarity and mayhem will ensue while the four sober actors try and keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
28. CHICAGO MYSTERY WALK
This self-guided mystery walk through Chicago’s North Loop is part puzzle game, part walking tour, and part pub crawl—and it’s a fun way to explore the city with friends.
You’ll follow clues on your phone that lead you past art installations, historic architecture, and tucked-away cafes and bars, all while solving a citywide mystery. There are slots available during the day, but honestly? Pub stops just hit better at night.
Start after sundown when the neighborhood is glowing, the bars are buzzing, and the whole experience feels more like a real-life detective story.
29. SPRAY PAINT + SIP WORKSHOP
Ready to channel your inner Banksy? This hands-on graffiti and street art workshop at Studio W.I.P. in Uptown lets you create your own mural-style canvas using spray paint and stencils—just like the pros.
No experience? No problem. A private instructor will walk you through the process step by step, so you’ll leave with something you’re proud to show off.
It’s BYOB, so feel free to bring your favorite drink and make it a chill paint n’ sip night with friends.
30. HAVE GAME NIGHT AT MIDLANE
Fancy a game night with your date, friends, or family members? Call up your favorite gamer friends and head on down to Midlane Esports for a night of fun!
At Midlane Esports, you pay by the hour so you can play unlimited games. Yes, unlimited!
Whether you are a casual gamer or take gaming seriously – there will be something here for you! With the Wombo Combo, you get two hours of gaming along with a game-themed cocktail, or bottomless soda and an appetizer – the choice is all yours.
Have a night of Nintendo nostalgia or a mainstream Fortnite party on the PS5 at the click of a button. They also have tabletop games too!
SAVE MONEY WITH GO CITY’S ATTRACTION PASS
On my last trip to Chicago, I used Go City’s Chicago All-Inclusive Pass. This easy-to-use mobile attraction pass really helped us see a lot of Chicago in a really short amount of time, and it helped us save a ton of money!
The Go City Chicago Pass is a digital attraction pass that provides easy access and admission to some of Chicago’s most popular museums and excursions. With certain excursions, you’re even able to skip the line, saving you both money and time.
There are two types of passes–the All-Inclusive Pass and the Explorer Pass.
The Go City All-Inclusive Pass is really great for travelers who want to see as much as possible while they’re in Chicago. With the All-Inclusive Pass, you can choose between a 1, 2, 3, 5, 6 or 7-day pass that will give you free admission to 25+ museums and attractions throughout Chicago.
The pass includes admission to the following heavy-hitters:
- Architecture River Cruise
- Skydeck Chicago
- 360 Chicago
- Shedd Aquarium
- Field Museum
- Museum Of Science And Industry
- Adler Planetarium
- Skyline Lake Tour
If you don’t plan on visiting a ton of different attractions, Go City also has an Explorer Pass which will still save you a lot of money. With the Explorer Pass, you’ll pay one flat fee for a 2, 3, 4, 5, 6, or 7-choice pass.
You’ll then have 60 days to use the Explorer Pass on whichever attractions you’d like. There is also no need to pick attractions ahead of time, so you’ll have the flexibility to choose attractions as you go.
You can buy the pass online here. Be sure to use a promo code before buying!
DEAL ALERT: For a limited time, use the above link + the promo code AFFGOALL for an additional 5% off your Go City pass. This code is valid for any Go City pass in any destination!
OTHER POPULAR ACTIVITIES IN CHICAGO
- Chicago Pizza Tour: Chicago’s only bus guided neighborhood pizza tour, includes 4 stops in different neighborhoods.
- Bikes, Bites, and Brews – Chicago’s Signature Dishes Bike Tour: Half-day bike tour featuring classic eats like Chicago dogs, deep-dish pizza, cupcakes and craft beer!
- Chicago Architecture River Cruise: A must-do for first timers! We did this tour and loved every minute of the cityscape views and the storytelling our guide used to teach us the history of Chicago.
- Chicago Crime and Mob Bus Tour: Explore Chicago while hearing stories about Chicago’s most notorious criminals and mobsters including Al Capone and John Dillinger.
ANNUAL EVENTS IN CHICAGO
If your travel dates fall within the dates of a festival or event, try to work it into your 4-day Chicago itinerary! Some of our favorite memories of travel destinations are from special local events that we happened to just stumble upon.
- SoxFest (Jan) – celebrating all things baseball
- Winter Brew (Jan) – beer festival
- Chicago Ale Fest (Feb) – beer festival
- Chicago Auto Show (Feb)
- Chicago Theatre Week (Feb)
- St. Patrick’s Day (March) – includes an annual dyeing of the Chicago River and huge parade
- Windy City BREWHAHA (March) – beer festival
- Chicago Restaurant Week (March)
- Chicago Comic and Entertainment Expo (April) – largest pop culture convention in the Midwest
- Chicago Memorial Day Parade (May)
- Maifest Chicago (May) – honors German heritage and the start of spring
- Gay Pride Chicago (June)
- Chicago Blues Festival (June)
- Taste of Chicago (July) – the world’s largest free-admission food festival
- Pitchfork Music Festival (July)
- Air and Water Show (August)
- Lollapalooza (August)
- Chicago Jazz Festival (September)
- Hyde Park Jazz Festival (September)
- Oktoberfest Chicago (September) – beer festival
- Chicago International Film Festival (October)
- Chicago Marathon (October)
- The Magnificent Mile Lights Festival (November)
- McDonald’s Thanksgiving Parade (November) – free parade featuring large marching bands, inflatable floats, and performance acts
- Christkindlmarket (December) – inspired by the epic German market in Nuremberg
- Fifth Third Bank Winter Wonderfest (December)
And there you have it–our top recommended things to do in Chicago at night! We hope this post helped you discover a new thing or two about Chicago’s nightlife scene. Happy traveling and adventuring!
You might also like:
4 Days In Chicago: Itinerary For An Epic Long Weekend
1 Day Chicago Itinerary For First Timers: The Must-Do Highlights
The Ultimate Lollapalooza Packing List: 21 Festival Essentials To Bring
Other Posts You’ll Love:
12 Epic Summer Festivals And Events Worth Traveling For
When summer rolls around, it’s easy to fall into the usual routine near home—long days…
15 Detour Destinations To Help You Get Off The Beaten Track
Big-name cities get all the attention — and all the inflated prices to go along…
Skip the Flight to Africa—These 12 Safaris in the USA Bring the Wildlife to You
I’ll be honest—I didn’t fully “get” the magic of safaris until I went to Safari…
Safari West: Experience A Slice Of Africa In California
Taking a trip to Northern California’s Sonoma County? If so, I’ve got an absolute must-do…
Got Plans This Fall? 10 Immersive Experiences Worth Traveling For
Fall is one of my favorite times to plan trips—not just for the crisp air…
23 Fun Things To Do In San Francisco At Night
The world has known San Francisco for its glory days. Cable cars, Golden Gate views,…