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Whilst synonymous with the blues, Chicago is one of the best cities in the USA not only for live music, but also for a fantastic night out too. In fact, you should never underestimate Chicago nightlife. It knows how to get the party started and how to keep it going. As the birthplace of house music too, if you are looking to kick up your heels on the dance floor, you won’t be disappointed.  

Music aside, there’s plenty of things to do when it comes to exploring the Chicago nightlife. As well as the thousands of incredible restaurants, there’s comedy clubs, burlesque and drag shows, all-season rooftop bars, distillery tours and more. Heck, why not even throw a mobs and molls tour into the mix too?! 

Read ahead for our guide to exploring the best that Chicago has to offer when it comes to nightlife, so you can plan your ultimate night out before you’ve even boarded the plane.

I guess that’s why they call it the blues

No one ‘does’ the blues quite like Chicago. It’s the sound of the city and there’s no better place to listen to that distinct sound than in the city where it was born. There are throwbacks to the fathers of blues all over the city which includes a massive mural of blues legend Muddy Waters on the side of a building at 17 North State Street, at the corner of State and Washington Streets. 

Today’s blues artists perform all over the city and a night out seeing blues is definitely one for the bucket list when it comes to Chicago nightlife. Head over to Buddy Guy’s Legends for seeing some of the best talent in town. This nifty nightclub has hosted an array of music stars from Bowie to Clapton and everyone in-between and get ready to get your blues on. 

blues club chicago
Instagram @buddyguys
ghost tour chicago
Facebook @GangstersandGhosts

Moll it over

Chicago’s reputation with Prohibition-era organised crime is notorious. If the streets of Chicago could talk, they probably would have some very interesting stories to tell. However, if you do want to dip your toe into the gangsters and molls of Chicago, then why not explore this rather grisly yet intriguing history on a Chicago crime tour. One of the most interesting tours that you can take part in as part of the colourful Chicago nightlife is a ‘Gangsters and Ghosts’ guided tour. They also run during the day, but make sure you opt for the 8pm one as ghost tours can only really be fully embraced at night don’t you think? 

Have a laugh

A huge part of Chicago nightlife is visiting a comedy club. Did you know that the Windy City is the birthplace of Improv? Chicago’s reputation as a comedy town is thoroughly well-deserved and has launched the careers of many top-notch comedians. 

From the historic The Second City in the old town that has helped launch the careers of many world-renowned comedians such as Tina Fey, Steve Carell and Bill Murray to the quirky and unconventional Annoyance Theatre there’s bound to be a laugh a minute.

stand up comedy chicago
Instagram @thesecondcity
night at chicago museum

Visit a museum after hours

Chicago’s museums are chock-full of the most amazing and immersive exhibitions that cover every genre and topic imaginable. The fun doesn’t have to stop when the sun goes down and day turns to night. As well as gazing upon the exhibits, there are also several events that you can enjoy as part of the Chicago nightlife scene.  

From concerts and cocktail parties to kids sleepovers and film screenings, take your pick from the nocturnal offerings across the city’s museums. From the Art Institute After Dark to the Museum of Science and Industry, there’s bound to be a museum for all tastes and interests.

Observe the city

From nocturnal drinks at rooftop bars to taking a ride on the Centennial Wheel at Navy Pier where you can soar to heights of nearly 200 feet, if you do just one thing when in Chicago at night, it has to include observing the incredible skyline after dark. Sure, there is more to the Chicago nightlife than just being sedentary, but sometimes you just have to sit and admire the striking cityscape that’s right in front of you. Weekend nights are the best time to visit the wheel as it’s open until 10pm and there are firework displays that add another level to the aesthetics of the skyline at night on Saturday evenings. If you prefer not to go round and round, why not head to one of Chicago’s rooftop bars or at the Chicago 360 or the SkyDeck, one of the top things to do in Chicago. 

view of chicago from skydeck
chicago night cruise

Take an architectural cruise

One of the highlights of Chicago is the architecture. Whilst you can walk the streets by day and head up to lofty heights to gaze upon the city, there is another way to explore the cityscape and a river cruise taking in the architecture is one of the most interesting parts of Chicago nightlife.  

You can tick off so many wins by taking an architectural river cruise. From helping you get your bearings, enhance your knowledge of the history of the city as well as getting some incredible photos of the buildings at night as the sun goes down. 

Trip the light fantastic in Chicago. From drinks in elegant bars to dancing the night away in one of the city’s nightclubs, download the Orbzii app today to Dream, Plan, and Book your holiday in Chicago today.