Are you looking for the best things to do in Chicago at night? Well, you’ve come to the right place!

If you’re searching for fun and interesting evening activities in Chiacgo, then keep reading because I’ve got some amazing ideas for you.

As the sun dips below the iconic skyline of the Windy City, it becomes alive with a vibrant energy, offering a myriad of exciting experiences for night owls and adventurers alike.

Whether you’re a local seeking to explore your city’s after-hours magic or a visitor eager to discover the hidden gems that glitter in the night, Chicago has something for everyone.

From world-class dining and electrifying entertainment to moonlit strolls along the lakefront and speakeasy-style cocktail bars, the nocturnal pulse of Chicago is undeniable, and there are so many fantastic things to do at night in Chicago to get involved with.

Join me on a journey through the enchanting nocturnal landscape of Chicago, where we’ll unveil the most captivating evening plans in Chicago, ensuring that your nights in this remarkable metropolis are as unforgettable as your days.

Now, let’s get into it!

Here are my favorite things to do in Chicago at night!

Enjoy some jazz music

To kick off our list, we’ve got a few of the city’s most famous jazz clubs!

Chicago has a rich history of jazz music, and there are several jazz clubs in the city where you can enjoy live performances.

There are so many wonderful jazz bars in Chicago, and we’ve listed a few of them below for you!

My personal favorites have to be Andy’s Jazz Club & Restaurant or Winter’s Jazz Club, but there are so many choices for jazz in Chicago, it only seemed right to list out a few more options on top of those!

  1. Jazz Showcase
  2. Constellation
  3. The California Clipper
  4. Fitzgerald’s Nightclub

Head on a sunset river cruise

There are so many river cruises in the city, and they all deserve a spot on this list of the best things to do in Chicago in the evening.

This 90-Minute River and Lakefront Cruise is one of our favorites, as it takes you past all of Chicago’s finest skyscrapers.

To make things even better, you’ll pass Buckingham Fountain’s light display while an expert guide tells you everything you need to know about the city.

Considering how much the tour covers, it’s an absolute bargain and is definitely one of the best nighttime activities in Chicago.

See the city from above

Our next pick for the best things to do in Chicago at night is seeing the city from above!

The Skydeck at Willis Tower is probably the most popular place to visit for excellent views, but 360 Chicago which is home to BAR 94 also offers incredible vistas over the city.

Wherever you choose to visit, make sure you take a few photographs to jazz up your Instagram grid!

Watch some live comedy

If you fancy a few belly laughs while you’re in Chi-Town, why not add a few comedy gigs to your list of evening plans?

Second City is probably the best place to visit for excellent comedy as it started the careers of stars like Eugene Levy, Bill Murray, and Steve Carrell.

And really, what could be better than that?

Explore the Chicago Riverwalk

If you’re on the hunt for things to do in Chicago at night, then you’ll want to add the Chicago Riverwalk to your list.

It’s a 1.25-mile stretch of pathway that takes you right along the Chicago River, and there are so many gorgeous views and skyscrapers to see along the way.

But it’s not just a gorgeous walk – it’s home to bars, outdoor performances, restaurants, and much more.

And plenty of places to stop for a photo too!

Not only will you be able to check out the amazing city lights, but you’ll be able to stop for a few cocktails as you “drink” it all in (pun intended!).

Read more about Chicago: 20 festive things to do in Chicago at Christmas time

Visit Lincoln Park Zoo

You might want to head to Lincoln Park Zoo while it’s still light out, but it also happens to be one of the best things to do at night in this amazing city.

You’ll have to plan your visit during the summertime, as this is when the zoo opens late on Fridays for craft brew tastings and late-night exhibits.

Go shopping at the Magnificent Mile

The Magnificent Mile is one of the most impressive shopping areas in the city and certainly deserves a spot on our list!

This enormous region includes more than 450 stores, so you can easily spend an entire day (and night!) indulging in a spot of retail therapy.

Although many of the stores close around 9 pm, there are a few shops that hang on until 10 pm during weekends and holidays!

Read more about shopping in Chicago: Where to find the best toy stores in Chicago

Visit one of the many rooftop bars

If you’re looking for things to do in Chicago at night, then you’ll totally want to swing by a few rooftop bars.

Cindy’s is one of the best spots to visit for views of Millennium Park, but Château Carbide and Nobu Chicago are the perfect pitstops for couples.

Failing that, swing by Z Bar for great drinks and even better views!

And remember – in the summer months, it stays light well into the evening, so you’ll be able to enjoy views way into the night!

Read more travel ideas: 15 best places to travel in your 20s, in the USA

Try and get out of an Escape Room

Is there anything more radical than an Escape Room? 

We don’t think so, which is why we’ve included one on our list of the best things to do in Chicago at night!

Although there are a few options dotted around Chicago, we suggest heading to Redline’s Virtual Reality Escape Rooms as they’re just so unique.

You’ll receive a headset for an hour and be able to choose between several different experiences.

And once you’re done, you’ll be able to hit the bar for a few pours!

Ride the Centennial Wheel

The Centennial Wheel is one of the most impressive attractions in the city, so it certainly deserves a place on our list of things to do in Chicago in the evening!

The wheel is an amazing 200 feet tall and it offers unbeatable views over the skyline and beautiful Lake Michigan.

The wheel is open during the day, but you can ride until 8 pm between Sunday and Thursday, and until 10 pm on Fridays and Saturdays.

Read more about Chicago: 28 fun things to do alone in Chicago

Head to the Alder Planetarium

The Alder Planetarium is tucked away in Chicago’s Museum Campus and it’s one of our all-time favorite things to do in Chicago at night.

Realistically, who doesn’t love stars?

The Planetarium is open throughout the day and usually shuts around 4 pm, but you can hang around until 10 pm on Wednesdays when Alder at Night runs! I suggest grabbing a ticket in advance as queues can get gnarly.

Head to a Bears game

Whether you’re a true-blue Bears fan or just want a taste of the Windy City’s sports culture, you’re bound to agree that heading to a Bears game is one of the best things to do in Chicago at night!

Getting a ticket for Soldier Field during peak periods (between August and September) can be tricky. 

But if you’re visiting during the cooler months, you should be able to nab a ticket.

Oh, and make sure you pick up a couple of beers and a few snacks while you’re taking in the atmosphere!


Next up, it’s a nighttime kayaking tour!

This is such a fun and unique way to spend the evening, and seeing the city’s skyscrapers from the water is so unique and different!

It’s a gorgeous way to spend the evening and such a great choice for spending an evening in Chicago!

Check out Buckingham Fountain

Next on my list of things to do in Chicago at night, is checking out the beautiful Buckingham Fountain.

Nestled in the heart of Grant Park, Chicago, the Buckingham Fountain is an iconic landmark that captivates both locals and tourists alike.

Known for its impressive water displays, the fountain takes on a whole new level of grandeur when the sun sets.

The nighttime shows at Buckingham Fountain are nothing short of magical, offering a mesmerizing experience that showcases the beauty of art and engineering combined.

Go ice skating

Next on our list of things to do in Chicago at night, it’s ice skating!

Although this is one of thethings one this list only open during the wintertime, you can usually sneak in a cheeky skate as late as March.

There are several skating rinks open throughout the city, but we suggest heading to Winterland at Gallagher Way or Light Up the Lake at Navy Pier for the best experience.

Check out Navy Pier

Speaking of Navy Pier, it takes the next spot on our list of the best things to do in Chicago at night!

In addition to an incredible range of bars and restaurants, you’ll be able to ride the Centennial Wheel, head on a classic carousel, and even catch a firework show if you’re visiting at the right time.

It spans an impressive 3,300 feet, so there’s plenty to enjoy along the pier up to 9 pm on weeknights and 10 pm on Fridays and Saturdays!

Read more about Chicago: Where to find the best desserts in Chicago

Watch the Chicago Symphony Orchestra

We love a bit of classical music over here, which is why we had to include a trip to the Chicago Symphony Orchestra on our list.

You’ll want to grab a bite to eat before taking your seat, but an average show should keep you occupied for at least a couple of hours from 7:30 pm.

The orchestra runs an incredible number of performances each year (over 120!), meaning you should be able to catch something during your visit.

Grab a few craft brews

We couldn’t write a list of the best things to do in Chicago at night without mentioning a bar crawl!

Bordel in Wicker Park is a fabulous place to visit for a few craft cocktails and pours, but you can also check out Crushed by Giants, Dovetail Brewery, or Pilot Project Brewing if you’re strictly on a beer run.

See the Bean at night time

Next on my list of things to do in Chicago at night, it’s seeing the iconic Bean.

This huge sculpture is a classic location in Chicago, but most people head over to it in the daytime, rather night.

But it’s so magical at nighttime too – so make sure you see it at both times of day.

Hop on the Chicago Night Crimes Bus Tour

Next on our list of things to do in Chicago at night, it’s the Chicago Night Crimes Bus Tour!

This is one of the more unique evening activities in Chicago, as it essentially takes you through the city as you uncover its spooky and crime-ridden past.

You’ll learn about famous characters like Al Capone and Bugs Moran, but you’ll also cover a few local massacres and haunted buildings as you move through the city.

The Green Mill Cocktail Lounge

Next on my list of things to do in Chicago at night, it’s some more jazz. Experience live jazz in a historic setting, and visit the Green Mill Cocktail Lounge.

The Green Mill Cocktail Lounge, is nestled in one of Chicago’s Uptown neighborhoods, and it is a timeless gem that has been enchanting patrons for over a century.

Stepping into this historic jazz club feels like a journey back in time, with its vintage decor, dimly lit ambiance, and an air of speakeasy mystique.

Known for its rich musical heritage, the Green Mill has hosted legendary jazz performers like Al Capone’s favorite, Joe E. Lewis, and contemporary artists who continue to serenade audiences with soulful melodies.

It’s a great choice for things to do at night in Chicago.

Grab food at Portillo’s

Next on my list of things to do in Chicago at night, it’s the famous Portillo’s!

Why am I recommending Portillos to you? Well, this little food court is home to TWO of my all-time favorite food items.

First of all, the best chocolate cake I have ever eaten. Ever. Apparently the secret ingredient is mayonnaise, but don’t let that put you off!

Portillo’s is also home to my favorite hotdog in the world too!

Museum of Science and Industry

The Museum of Science and Industry in Chicago is not just a place for daytime exploration; it truly comes alive during its special evening events featuring interactive exhibits. Which makes it a great choice for things to do in Chicago at night.

As the sun sets over the city, the museum transforms into a captivating playground of science and wonder, and it’s such a fun choice for things to do at night in Chicago.

These unique events allow visitors to engage with science in a whole new way, often featuring hands-on experiments, immersive displays, and interactive demonstrations that spark curiosity and ignite the imagination.

It’s a perfect blend of education and entertainment that appeals to both the young and the young at heart.

Chicago Botanic Garden

Next on my list of fun things to do in Chicago at night, is enjoying evening garden walks at the Botanic garden.

Many people don’t even realise the Botanic garden is open past sunset, so this might come as a pleasant surprise!

As twilight descends over the meticulously manicured gardens, the garden’s allure takes on a whole new dimension, and exploring at night (only during the warmer months) gives the gardens even more appeal.

From late spring to early fall, visitors can partake in a variety of evening events that showcase the garden’s natural beauty and serenity under the moon and stars.

Go for deep-dish pizza

Chicago is renowned for its deep-dish pizza, so that’s my next suggestion!

Find yourself a pizzeria and dig in!

There are several iconic pizzerias in the city that serve up this delicious, hearty dish that Chicago is so famous for! Here’s a short list of some of the best places to enjoy deep-dish pizza in Chicago:

  1. Lou Malnati’s: A Chicago institution, Lou Malnati’s is famous for its buttery, flaky crust, tangy tomato sauce, and generous cheese toppings. Their “Lou Malnati’s Special” is a must-try.
  2. Giordano’s: Known for its stuffed deep-dish pizza, Giordano’s offers a thick layer of cheese encased in buttery crust and topped with a chunky tomato sauce. It’s a cheese lover’s dream.
  3. Pequod’s Pizza: What sets Pequod’s apart is its caramelized crust, which forms a deliciously crispy edge.
  4. Art of Pizza: This pizzeria offers a variety of deep-dish options, from classic to creative. Their stuffed spinach and mushroom pizza is a favorite among locals.
  5. My Pi Pizza: My Pi Pizza specializes in “authentic Chicago-style pizza,” offering a dough recipe that originated in the 1950s. A perfect choice for things to do in Chicago at night!

Read more about Chicago: 13 of the best places to get pizza in Chicago

Late-night bowling

Next up on my list of fun things to do in Chicago in the evening, it’s nighttime bowling! Who doesn’t love a game or two?

This is one of my personal recommendations and favorites, because I love visiting a bowling alley like Lucky Strike, and have a few games of bowling during the evening!

During a busy sight-seeing vacation, a game or two of bowling can be a nice change of pace too!

Late-night food trucks

Next in my list of things to do in Chicago at night, it’s one for the foodies!

Satisfy your cravings for tacos, pierogies, and more… and head to one of Chicago’s many famed late-night food trucks.

Maybe you didn’t know, but this city is kind of famous for their late-night food truck scene, and you can get some seriously incredible eats this way!

Some great food trucks to look out for are:

  • The Fat Shallot
  • 5411 Empanadas
  • Chicago Pizza Boss
  • The Roost Carolina Kitchen
  • Aztec Dave’s Food Truck
  • Yum Dum Truck

Late-night karaoke

Next on my list of nighttime activities in Chicago, it’s sing your heart out at a karaoke bar.

Whether you’re sober (or not), karaoke is one of those night-time activities that is fun, breaks the ice, and gets everyone in a great mood.

Lucky for you, Chicago has some fantastic Karaoke bars right in the heart of the city too!

  1. Brando’s Speakeasy – Located in the Lakeview neighborhood, Brando’s Speakeasy offers private karaoke rooms in addition to the main bar area. It’s a popular spot for both casual karaoke nights and special occasions.
  2. Lincoln Karaoke – Situated in Lincoln Park, Lincoln Karaoke is a spacious karaoke lounge with a vast song selection and private rooms for groups of various sizes. They also serve drinks and Korean cuisine.
  3. The Globe Pub – This North Center sports bar hosts karaoke nights that are beloved by locals. It’s a friendly, neighborhood spot with a wide range of songs to choose from and a welcoming atmosphere.
  4. Blue Frog’s Local 22 – Located in the River North neighborhood, Blue Frog’s Local 22 offers karaoke along with a menu of bar food and a diverse drink selection. It’s a lively place for both singing and socializing.
  5. Beauty Bar – Nestled in the West Town neighborhood, Beauty Bar is a unique venue that combines a beauty salon and a bar. They often host karaoke nights, adding an extra layer of fun to your evening out.

Remember to check the specific days and times for karaoke events at these venues, as they may vary.

Take a swing at Topgolf Chicago

To round off our list, we have Topgolf Chicago which is always a huge crowd-pleaser!

Although it’s a small trek from the center of Chicago, it’s well worth the extra time.

This impressive complex boasts over 200 enormous TVs for watching sports, firepits for cozy catchups, and of course, plenty of competitive golf games!

Whether you choose to take a swing or take it easy at the bar, this is so much fun!

I hope this list of things to do in Chicago at night was useful!

Which of these activities are you most excited for?

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