20 Best Things To Do In Chicago At Night

The bustling urban city of Chicago is brimming with things to do in the daytime. I mean, it’s one of the best world-class cities in the United States–how could you be bored?

From taking selfies at The Bean in Millennium Park to munching on deep-dish pizzas to exploring large and epic museums all around town, visitors can easily fill their days up with exciting activities.

But what is there to do in Chicago at night exactly? Well, we’re here to tell you that Chicago at night is something else!

In a city as large and magical as Chicago, it’s easy to see why Chicago comes even more alive in the nighttime! From karaoke bars and rooftop bars to speakeasies and museums after dark, there is no shortage of nighttime activities in The Windy City! Here are the top things to do in Chicago at night.

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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
  • Being a very windy city, hence the nickname, “The Windy City”
  • Navy Pier, one of Chicago’s most famous landmarks and a popular tourist destination
  • Wrigley Field, home to the Chicago Cubs
  • The Chicago Riverwalk, a pedestrian area lining the Chicago River that features plenty of restaurants and resting spots to enjoy the river

20 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

Chicago 360 at night

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. Both are also included with the Go City Chicago Attraction Pass!

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

The Goodman Chicago - TravelsWithElle

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 while in Chicago:

  • Cadillac Palace Theatre
  • Briar Street Theatre
  • Steppenwolf Theatre
  • Auditorium Theatre

3. TAKE A SUNSET RIVER CRUISE

Chicago Sunset Cruise - Best Things To Do In Chicago At Night

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 did we mention you’re going to be an architecture pro after your cruise? Trust us, they are a lot of fun.

While a daytime river cruise is a fun activity, the architecture river cruises at night, held after dark or at sunset, are even more beautiful. You’ll get the added perk of seeing the city skyline lit up, from a really unique perspective!

There are also dinner cruises available which include either a 3-course meal or a buffet, music, drinks, and more.

4. TAKE THE GANGSTERS AND GHOST TOUR

Want to learn about Chicago from a truly unique perspective? With a historian as your guide on the Gangsters and Ghosts Tour, you’ll step back to the roaring 20’s, 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, the Gangsters and Ghosts Tour in Chicago 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

Museum of Science And Industry - 1 Day Chicago Itinerary

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 for example:

  • 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

7. DO THE CHICAGO RIVERWALK

Chicago Riverwalk - 4 Day Chicago Itinerary - TravelsWithElle

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 At Night Chicago Illinois

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.

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

Second City Comedy Chicago

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. Second City, Laugh Factory, The Comedy Bar, and Annoyance Theater are all 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

Green Mill - Best Things To Do In Chicago At Night

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

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. If you and your group are looking for things to do in Chicago at night and are willing to flex those brain muscles, you should definitely consider doing an escape room!

The Escape Game is the most popular escape room company in Chicago. You can pick from themed rooms such as Gold Rush, Mission Mars, Special Ops, The Heist, and Prison Break.

Once you arrive, you and your friends/family members must work together to find clues and solve puzzles in a set amount of time to ultimately escape!

Pro Tip: The Escape Game experience is included in some tourist passes like the Go City Chicago Card.

14. GO DANCING AT A NIGHTCLUB

Pool Party Spring Break - Cancun In March - TravelsWithElle

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

Nightlife in Chicago - 1 Day Chicago Itinerary For First Timers - Travels With Elle

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

Sakura Karaoke Bar Chicago IL

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

Wrigley Field Chicago

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, Adler Planetarium holds a 21-and-up after-hours event that invites adults 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 MAGIC SHOW

Chicago Magic Lounge - Best Things To Do In Chicago At Night

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

Lincoln Park Ghost Tour
Courtesy of GetYourGuide

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!


CONSIDER GETTING THE GO CITY CHICAGO 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.

Prices start at $95 for the All-Inclusive Pass and you can visit literally as many attractions as you can fit into each day!

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. Passes start at $59 for 2 choices.

You can buy the pass online here.

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!


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)

ESSENTIAL PACKING LIST: CHICAGO, ILLINOIS

  • Comfortable walking shoes | You’re going to be doing a lot of hill climbing, so bring comfortable walking shoes. My all-time favorite travel shoes these days are the tried and true Ecco Soft 7‘s (they’re stylish, comfortable, and have been raved about for decades since they were first created)! Lucky for us, they have them for both men and women.
  • Smartphone UV Sanitizer and Charger | Our phones gather all the grime and bacteria we touch throughout the day, and then they are stored in warm, dark places like purses and pockets, which make for great breeding grounds for bacteria to grow. They are the third hand we never wash, but should! Using a UV sanitizer such as PhoneSoap on a regular basis will help keep germs and illness at bay.
  • First Aid Kit | It’s always good to carry a first aid kit around with you when traveling. If you need to pack light, simply make one of your own (pain medications, bandaids, motion sickness pills, etc.)
  • Portable Umbrella | You’re going to be in The Windy City. If you’re going to bring an umbrella, make it a compact, wind-proof umbrella like this one!
  • Light Rain Jacket | A lightweight waterproof rain jacket is critical for any destination with unpredictable weather. Since these weigh virtually nothing and are so easily packable, I recommend you carry one with you whenever you head outdoors. Depending on the weather forecast and chance of precipitation, I’ll either go with a rain shell or a puffier windbreaker. I’m never without some sort of outer layer! My top recommendations are Marmot Men’s PreCip (for men) and The North Face Women’s Venture 2 Jacket (for women).
  • Puffy Jacket | If you’re traveling in the fall or wintertime, you’re going to need layers. You have a lot of options here, but I personally have the North Face Thermoball, and it’s kept me warm throughout my many years of adventuring!
  • Travel Daypack | I’m a huge fan of the Fjallraven Kanken Mini Backpack. It stylish and has ample room for all the snacks and water you’ll need, as well as for your camera and the safety essentials for a hike or just a regular day out.
  • Sunhat | Sun protection is key for any destination, anytime.
  • Sunscreen | Sunscreen is absolutely necessary. Even if it’s overcast or cloudy, the UV index can be very high, so be sure to apply whenever you’re outdoors. No matter where we go, we like a coral reef-safe brand, as traditional sunscreens contain chemicals that damage our environment. For the face, we are absolutely obsessed with the magical Supergoop! Unseen Sunscreen.
  • Hand Sanitizer Hand sanitizer gel or wipes are a must any time you’re going to be in contact with surfaces many other people have touched. Never leave your hotel room without it! And if you do happen to forget it, remember to wash your hands often, especially before eating or touching your face.
  • Body Wipes / Feminine Wipes | Feeling a bit gross after a hike or bike ride but don’t have the time to shower right in that instant? Just whip out one of these body wipes for a quick refresher. The feminine wipes I like are infused with cucumber and aloe. Trust me, you will feel and smell so much better. Always good to have a few handy in your travel bag.
  • Portable Power Bank | You’re probably going to be out all day, snapping away taking pictures… the last thing you want is to be driving along with no phone battery! A portable power bank is a must-have, and Anker’s ultra-light, ultra-portable power bank is tried and true by so many travelers! I never embark on a day of exploration without it.
  • Soft Hydration Flask | Stay hydrated throughout the day with a water bottle that can go anywhere with you—and fold up when not in use. I love the packability of these bottles!
  • Emergen-C packets or Liquid I.V. Hydration Packets | These are a great way to support your immune system and overall health on a trip. They are light, take up no space, and are very easy to pack!

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!

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