Chicago‘s neighborhoods offer late-night entertainment far beyond the city’s skyscrapers, including secret magic shows, small-group improv performances, and pub crawls. Feeling interested? Here are the best things to do at night in Chicago that will make you fall in love with this city.
Cruise the Chicago river
If you’re not in a rush, spend a whole evening on the Chicago River cruise enjoying meals, beautiful vistas, DJ entertainment, and dancing as you take a dinner cruise.
You can savor chef-prepared plated dinners, inventive beverages, exemplary service, and spectacular views of Chicago’s skyline and landmarks from the open-air outdoor deck while onboard.
- Chicago Architecture river cruise
- Chicago sunset cruise
- Chicago dinner cruise
- Lake Michigan sightseeing cruise
The dinner cruises are the ideal way to enhance any occasion and view Chicago from the water, whether for a special supper for two or a romantic evening with friends and family.
Join the Gangster and ghost tour
Chicago can be seen through mystery criminals and ghosts if you choose.
Do you want to learn about this magnificent American city’s history from the beginning, starting with the original sites?
With many 2-in-1 historical guided tours of Chicago’s gangsters and ghost stories, starting from the renowned Chicago Loop Vice District, you may get the best of both worlds!
Since the 1920s and 1930s, when there was murder and mayhem down every alleyway, Chicago has had a colorful gangster history that is well-known worldwide.
With your tour guide, you’ll travel back in time to the Roaring Twenties, when the Chicago Loop was home to speakeasies, bootleggers, and notorious gangsters like Al Capone.
Visit eerie locations, including Death Alley, the Congress Hotel, and the Palmer House, which were once mafia hangouts, or discover the dark past of the Loop, one of Chicago’s most popular neighborhoods.
Get hands-on with Paint’ n’ Sip
Looking for a creative outlet that’s entertaining and original? With Paint ‘n’ Sip workshops, you can let your inner street artist go.
What is your favorite beverage? Bring it with you and cheer while enjoying your painting session.
Get ready to pick up some spray paint and make a unique item during this interactive workshop. Also, you’ll learn the tricks of the trade for using stencils.
Not the most artistically inclined individual? Fear not! Artists and staff from the studio will be curating this session. You get to take your canvas home once the workshop is over!
Try indoor skydiving
Nothing else compares to the sensation of indoor skydiving, and there’s no better option than iFly.
The cutting-edge wind tunnels at iFLY are built to deliver a safe flight experience, lifelong memories, and a distinctive tale to share!
The age range for indoor skydivers is 3 to 103. People of all ages, sizes, and skill levels can fly and have a great time, from novices to seasoned pros. You don’t have to be an athlete or in excellent physical condition, so don’t be worried.
Admire Chicago from observatory decks
What can you see from the Observation Deck? Actually, let’s make this query: What cannot be seen from it?!
In a city known for its architecture and cityscape, you’ll want to discover what’s on the horizon at this must-see attraction.
John Hancock 360 Chicago Observation Deck
You can have astonishing views of downtown Chicago and Lake Michigan from the John Hancock Observation Center’s 49th floor.
The iconic Chicago, Illinois skyline is visible from every angle from John Hancock Center. When the skies are clear, you may see up to 80 kilometers and as far as four states with 360 Chicago Deck. There’re several events to check out, such as photography nights, guided tours, and musical evenings.
Willis Tower Skydeck
Willis Tower is a well-known structure and a fun Chicago trivia treasure trove. It stands 1,450 feet and 110 floors tall, making it the eighth-tallest structure in the world and the tallest in the Western Hemisphere.
The glass boxes of The Ledge, which are 1,353 feet above the ground and extend 4.3 feet from the skyscraper’s 103rd-floor Skydeck, offer never-before-seen views of the city. You don’t want to miss it, trust us!
Enjoy the shows
You can also have a fun night in Chicago with several amazing entertainment shows.
Drunk Shakespeare Performance
Each show at Drunk Shakespeare Performance is unique, depending on the audience’s drinking habits!
After downing five whiskey shots, a professional actor tries to act in a Shakespearean play. The four sober performers struggle to keep the script on track as chaos and humor take over.
Get your tickets now for Drunk Shakespeare if you’re a theater addict because it has a short run!
Trickery Chicago magic show
Every time you visit, you can expect a wonderful experience thanks to cocktails, enchantments, and surprises.
Chicago symphony orchestra
The Chicago Symphony Orchestra, founded in 1891, is frequently acknowledged as one of the world’s finest ensembles.
It has a wide variety of music, from Baroque to modern. The CSO’s brilliant players, who perform in over 150 concerts annually, are the heart and soul of the ensemble.
The Chicago Theatre
Chicago Theatre debuted in 1921 and was the country’s first opulent movie palace and home to the renowned, six-story-tall “C-H-I-C-A-G-O” marquee. This historical stage has hosted some of the biggest stars and most glitzy musicals in history.
Sample Chicago’s best eats
Regarding signature meals, Chicago is in a class by itself. Chicago is known for its four signature foods: deep-dish pizza, Chicago-style hot dogs, popcorn, and Italian beef sandwiches.
So whether you’re an experienced or a foodie novice, try them on your visit.
For the best experience, you can join food tours and explore the culinary scene with a guide:
Explore Navy Pier
You can’t skip the fascinating Navy Pier! The enormous indoor/outdoor facility on Lake Michigan’s beaches has long been a popular attraction in the Midwest.
Recent improvements have changed its status from a lovable tourist hub to a popular destination for local foodies and entertainment.
You want to make the most of the nearly 50 acres, right?
Navy Pier doesn’t have to feel as big as it appears, although it sometimes feels like a city within a city.
Here, at Navy Pier, there’re excursions, activities, gathering spots, dining establishments, and much more that you must not miss.
Solve puzzles in an escape room
Your team may interact in new ways by playing an escape game in Chicago.
It offers fantastic icebreaker opportunities and a mental shift that can help you hone your problem-solving skills. These challenging activities involve solving riddles and clues, and players may want to beat the clock.
Marvel at the Chicago skyline from a helicopter
On this 15-minute helicopter tour, you will see Chicago from above.
Don’t forget to take pictures of the beautiful cityscapes as you soar over Chicago’s downtown. View attractions like Soldier’s Field, Shedd Aquarium, and the Willis Tower (home of the Bears).
Be ready to take a seat in a roomy, comfortable helicopter and feel the rush of taking flight.
Listen to live music
Jazz – Green mill cocktail lounge
The Green Mill Cocktail Lounge, which has been around for more than a century, is the pride of Chicago’s Uptown district and the world’s greatest jazz venue.
You may unwind, sip martinis or Schlitz, and enjoy some of the best music available at Green Mill, featuring anything from swing orchestras to traditional jazz.
Every Sunday night, it even conducts the oldest poetry slam. The Green Mill, modeled after the Red Mill at the Moulin Rouge in Paris, has played host to many famous people, including Frank Sinatra and Bill Gates.
It was also a location for The Untouchables, High Fidelity, and the Crime Story TV series from the 1980s.
Blues – Kingston Mines
The oldest and biggest blues club in Chicago, Kingston Mines, was established in 1968.
Kingston Mines have received several awards for outstanding performances and passion over the years. Magic Slim, Koko Taylor, Billy Branch, Junior Wells, and numerous other musical legends have performed on its two stages.
Hop on the Chicago night crime bus tour
Throughout the generally two-and-a-half-hour Chicago crime bus tour, you will be able to discover Chicago’s “dark side.”
What is that? The bus delves into great detail into the lives of infamous organized crime figures, including Al Capone, Bugs Moran, and others.
Discover notorious crime scenes like the St. Valentine’s Day Massacre, discover “The Enforcer’s Safe,” and visit neighborhood bars.
Grab your camera for a drive-by shooting of famous historical and architectural monuments, and scout for crime locations, including the Biograph Theatre, Holy Name Cathedral, and St. Valentine’s Day Massacre, one of Chicago’s most infamous murder sites.
Following through the footsteps of notorious Chicago bandits John Dillinger and Hymie Weiss until their demise and exploring the criminal past of the Chicago neighborhoods might be an experience that you will never forget.
Stroll Chicago Riverwalk
Situated on the south bank of the Chicago River, the award-winning, pedestrian-friendly Chicago Riverwalk extends 1.25 miles from Lake Michigan to Lake Street.
Along the route, you’ll come across private coves, airy cafes, wineries, and pubs, as well as public artwork, monuments, museums, and a boatload of water trip options.
See Buckingham fountain at Grant park
Grant Park has something for everyone, including nature lovers, fans of public art, and architecture enthusiasts.
You shouldn’t miss its star, the magnificent Buckingham Fountain, situated in the middle of the park.
Buckingham Fountain comes to life at dusk with breathtaking light and music performances every hour.
Don’t miss the hourly, 20-minute water show, taking place during the day, and features the main jet of the fountain spewing water 150 feet into the air. From May through the middle of October, the fountain is operational.
Sip cocktails from rooftop bars
An outside drinking setting is something Chicagoans adore. The city has dozens of fantastic elevated options every year, including old faves and tantalizing debuts.
Take advantage of the cozy atmosphere, grab a drink, and choose one of Chicago’s best rooftop bars, including Avec, The Up Room, and Devereaux.
FAQs about things to do at night in Chicago
What is Chicago famous for?
Chicago is one of the most well-liked tourist attractions in the United States. It has a diverse reputation with its festivals, music, and culture. It would take weeks or perhaps months to see everything this city offers.
What is the nightlife like in Chicago?
Well, Chicago may not be as vibrant as other cities like San Francisco and New York, but it has a different charm after dark. Adventurous, mysterious, and romantic are what we think about this place.
What area of Chicago is best for nightlife?
Most of Chicago’s nightlife is centered in an area north and northwest of downtown. While there’re nightclubs in every neighborhood in the city, most of them are reserved for locals, so you may not feel at home there.
Hope that you get the idea of what to do in Chicago after reading our recommendation. We cannot wait until your trip to this beautiful city!