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13 Unmissable Things To Do In Chicago At Night

Published by: Bounce18 July, 2022

The first things that come to mind when people think of Chicago are Michael Jordan, deep-dish pizza, and The Bean. While these things all have their merits, there is so much more to Chicago. The Windy City is a world-class travel destination. Chicago parks are second-to-none, with Millennium Park, the Lincoln Park Zoo, and Grant Park all hosting thousands of tourists every summer. The Chicago restaurant scene is brimming with Michelin stars and celebrity chefs, and the nightlife is exceptional. Chicago museums also offer late-night events and programming that are all perfect for a night out in Chicago. 

With so much to choose from and explore, dropping your luggage off at a Bounce storage facility in Chicago is the perfect way you can conveniently cram everything into a short stay. Here are the best things to do in Chicago at night:

Visit A Museum During Their Nighttime Hours

While most museums tend to close up shop around 6 or 7 pm, there’s always the chance that your stay in Chicago coincides with one of the “after hours” events held at one of the world-class museums and institutes. Nearly every museum programs events and exhibits throughout the year that keep the facility open long into the night. And these aren’t stripped-down events either; some of the best exhibits happen after hours. 

Many of these are adults-only events, with full bars offering beverages or food so that the moms and dads (and anyone of drinking age) can enjoy a night out and learn a thing or two. One of the best features of these events is that the crowds are much smaller, so exploring and appreciating the exhibits is easier and more enjoyable. 

Some examples of the exciting nighttime events are Art Institute After Dark, Chicago History Museum Happy Hour, Adler After Dark, Museum of Science and Industry After Hours, Museum of Contemporary Art Prime Time, and Shedd After Hours. Check the museum calendars to find out when events are taking place and how to buy tickets. 

Take In A Show at a Theatre 

You don’t need to travel to Manhattan to see a Broadway show. Chicago has a number of classic theaters that showcase every type of performance. All of the blue-chip touring plays generally make a stop at Chicago’s Auditorium Theatre, and many of the best up-and-coming theater companies are promoted by The Goodman Theatre, CIBC Theatre, Studebaker Theatre, and others. Most of these historic theaters are located in The Loop near the other must-visit attractions like Millennium Park, the Art Institute, and Michigan Avenue (the Magnificent Mile).  

If you want to experience a true Chicago institution, the Steppenwolf Theatre is your best bet. This long-running theater company has counted some of the best and brightest actors among its ranks, and the roster of alumni is truly impressive. Located in nearby Lincoln Park, Steppenwolf is a must-hit for theater lovers!

Hit Up One of Chicago’s Best Music Venues 

Chicago is a world-class live music city. Not only does the city host hundreds of thousands of music fans at festivals like Lollapalooza, Pitchfork, and Riot Fest, the sports stadiums like Wrigley Field host the largest touring acts in the world for unforgettable concert experiences. When you’re in Chicago during the colder months, there are still dozens of music venues across the city that host every type of musical act possible. From gritty rock clubs and jazz bars to historic opera houses, Chicago has it all. Here are the best music venues to catch a show at: 

The Chicago Theatre 

This historic downtown venue is famous for its iconic marquee and incredible baroque interior. It’s walkable from all the best that The Loop has to offer, so it’s perfect for a full night out on the town! Expect blue-chip rock and pop performers to perform here, along with the best standup comedians, at least the ones that aren’t selling out United Center. 

Empty Bottle  

If Blue Man Group and Chicago Symphony Orchestra aren't your things, then the Empty Bottle might be calling your name. This is the epicenter for Chicago hipsters. The garage rock-oriented roster and charmingly shabby decor add to the vibe. The cheap beers and slightly out-of-the-way location only add to the experience. Expect the best up-and-coming bands to play Empty Bottle, but they do get legacy acts, who would normally play larger venues, for special one-off performances! 

Thalia Hall 

Located in ultra-hip Pilsen, Thalia Hall is housed in what might be the coolest building in Chicago. Not only is historic Thalia Hall the premier indie music venue, but the popular Dusek’s Tavern and Punch House cocktail bar are both located downstairs. 

Metro 

One of the elder statesmen of Chicago’s music scene, The Metro is located down the street from Wrigley Field and hosts everything from indie rock to hip-hop to classic rock shows. 

Green Mill 

Located in the Uptown neighborhood, Green Mill is Chicago’s most iconic jazz club. On weekends, there’s a line out the door for groups pining for a table to watch all-night jazz sets. No tickets are required, but there’s a cover at the door.

Explore Chicago’s Mob History 

Whether it’s Al Capone’s status as a local icon or the prominent mob museum, Chicago proudly displays its sordid history of criminal activity. During Prohibition and the Roaring ’20s, the Windy City was a hotbed for bootleggers and gangsters. There were hundreds of speakeasies, casinos, and brothels throughout the city, all being operated by a truly colorful cast of characters. The larger-than-life Al Capone is still one of the most recognizable Chicago figures. 

Chicago’s near northside areas like River North and Gold Coast have some well-preserved historical buildings that housed the most notorious bootleggers, like the Congress Hotel and Palmer House. There is even a place called Death Alley that can be visited by historians and enthusiasts. There are a few companies that give walking guided tours of these areas, with knowledgeable guides that offer up both informative and chilling tales of Chicago gangster activity during this period. 

The Chicago Night Cromes Bus Tour is another way of seeing these sites and is a great way to get to know the near north side. You’ll see where the St. Valentine's Day Massacre took place and stop at hangouts where Capone, Johnny Torrio, Bugs Moran, Dean O’Bannion, and Frank Nitti all hung out and carried out their nefarious business. 

Enjoy Chicago’s Best Rooftop Dining 

The Chicago skyline is one of the most iconic visuals you can experience, and luckily, there are dozens of rooftop bars where you can sip on a cocktail and enjoy the view. If there is a bar, open air, and views, you can’t go wrong. But here are the best rooftop bars in Chicago: 

Most of the best rooftops are in The Loop, especially hotels located on the roof of LondonHouse, LH On 22 (Wacker Drive) and a number of premier bars on the Magnificent Mile. The Hotel Lincoln’s J Parker Bar is a popular destination for hip 20-somethings. The uber-stylish Cindy’s is the rooftop bar at The Chicago Athletic Association Hotel that has blown up in popularity in recent years. 

Another popular destination for rooftop cocktails is the ultra-trendy West Loop area, where dozens of buzz-worthy restaurants and bars open seemingly every day. The location allows for stunning skyline views, and these bars have some of the best cocktail menus in the city. 

Get Unforgettable Views (and Fireworks) at Navy Pier 

Navy Pier might seem like an obvious destination, but it's popular with tourists for a reason. Stretching more than six city blocks, Navy Pier juts out of downtown Chicago to offer stunning views of the skyline, Lake Michigan, and even the museum campus. 

There are hundreds of activities and attractions along the pier, including an IMAX Theater, a museum chronicling the history of Chicago, and an arcade. The most notable attraction has to be the massive Ferris Wheel that’s perched atop the pier. Given the location, it’s safe to say that the top of the wheel provides the absolute best vantage point of downtown Chicago. Even better, every summer, there are firework shows on Saturday nights and holiday weekends. Passes to the Ferris Wheel for adults are $15. Admission to the Pier is absolutely free, so it’s incredibly convenient to walk from a hotel in The Loop or from the train. 

Take In An Improv Comedy Show 

Almost as quintessentially Chicago as deep-dish pizza and Bulls jerseys, improvised comedy is a beloved tradition. The Second City is a comedy company located in Old Town that focuses on teaching improv and also promoting comedy shows that showcase local and rising talent. Some of the most legendary names in comedy have come through Second City, including Bill Murray, Chris Farley, Tina Fey, and hundreds of others. Second City continues to be a feeder to current SNL casts, and future stars are currently training and performing there. Other improv and comedy shows to check out are Improv Olympics, Zanie’s, and Bye Bye Liver, all of which are the perfect group activity for a night out. 

Hit The Lincoln Park Zoo for Zoo Lights 

During the day, Lincoln Park Zoo is buzzing with families and groups of every sort enjoying the Lake Michigan breeze, sun, and hundreds of different animals. But a few times of the year, the zoo opens its gates for ticketed events at night. Zoo Lights is a popular adults-only event that brings bars, a DJ or a live band, and plenty of cool light fixtures. Check the calendar because this is one of the coolest things to do in Chicago at night every year!

Go Bar Hopping In Chicago’s Hottest Neighborhoods 

Chicago’s neighborhoods are the best way to experience the culture of the city. These are distinctive neighborhoods with their own vibe and character, so there’s something for everyone in Chicago. The city’s nightlife is very eclectic. There are nightclubs, sports bars, craft breweries, cocktail bars, barcades, dive bars, and everything else you can think of. 

If anyone has called you a hipster, head to Pilsen or Logan Square for trendy cocktail bars, incredible restaurants, and ironic and unironic dive bars. Looking to dance until the early hours? River North is the epicenter for luxury nightlife (bottle service included). Lincoln Park and Lakeview, especially Wrigleyville, are great for sports bars and stylish restaurants. 

Check out our neighborhood guide to find the best area to plan an epic night out, and it can also help you find where to stay in Chicago.

Enjoy The Chicago Riverwalk

While the Lake Michigan shoreline gets all the attention, don’t sleep on spending an afternoon kayaking down or strolling by the Chicago River. The Chicago River snakes through the northern neighborhoods, through downtown, and out to the southwest side. While in past decades, the river was largely industrialized, there has been great investment into the Riverwalk to make it one of the best features for travelers to enjoy. The mile-and-a-half stretch off the river near Michigan Avenue and Wacker Drive is bustling with bars, restaurants, and activities. Kayak rentals are popular, and you can even grab one at night, which makes it perfect for appreciating the incredible lit-up architecture. All the action is near the John Hancock Observatory, the Magnificent Mile, and the theatre district. Some of the best street food in Chicago is here, too, so grab a bite before or after your walk or kayak.

Hit Up a Neighborhood Street Festival 

Each summer, just about every Chicago neighborhood closes down its main street, sets up a few stages, and invites the best local businesses to set up tents and stalls to sell their art, food, crafts, and beverages to locals. Each street festival is free to attend, with a suggested donation benefiting the neighborhood chambers of commerce. This is the perfect opportunity to take a break from Millennium Park, Navy Pier, and the Willis Tower, and you'll truly see how locals live.

Local and national touring acts are booked to play these events, with headliners that are big enough to play the proper music festivals! This is a great way to explore the neighborhood, and if you want to see some happy locals, just people-watch at a street fest! Chicago’s best street vendors all open up stands or bring their food trucks to serve the tastiest bites in the city. 

Here are just a few of the best street festivals in Chicago: The Taste of Randolph, Wicker Park Fest, West Fest, Logan Square Arts Fest, and Square Roots.

Take In a Sporting Event 

In any given month, there are at least two sports teams playing in Chicago at night. The Chicago Cubs and White Sox play baseball in the summer, with 82 home games for each team. From spring to fall, there’s a great chance at least one of them will be playing during your stay in Chicago. You can head to the lakefront to see a Chicago Bears football game or Chicago Fire FC Soccer game. During the winter, The United Center hosts either the Chicago Bulls or Blackhawks for games basically every night. 

Chicago is a massive sports town. With passionate fans and iconic sports stadiums, these experiences are perfect for getting to know a city. And Wrigley Field looks pretty nice for that Instagram pic!


Hit The Magnificent Mile for a Nighttime Shopping Spree 

Chicago’s Michigan Avenue, better known as “The Mag Mile,” is one of the best stretches of luxury retailers in the entire country. The most prestigious global brands all have a presence either on Michigan Ave or at nearby John Hancock Center and Chicago Watertower Place. If you're visiting Chicago during the holiday season, this area lights up with gorgeous decorations, lights, and Christmas trees. The best way to experience this is to bundle up (because the breeze off of Lake Michigan is less friendly during the winter) and get all your holiday shopping done! After getting your retail therapy, head to Millennium Park for ice skating or see the lit-up Navy Pier.

Conclusion

Day or night, Windy City has so much to offer. The city is set up for locals and visitors to enjoy the Chicago River, Lake Michigan, and the Chicago skyline, even after the sun goes down. The nightlife, music, and dining scenes are all world-class as well. Even the historic museums and theatres are open and ready to entertain. So drop your luggage with Bounce so you can enjoy your night out in Chicago! 

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