What’s your idea of a great night out? Dancing till the early hours, catching a new comedy act, or enjoying a classic cocktail in a retro bar? Wherever you’re thinking of stepping out, you can’t put a foot wrong in Chicago.

Discover the best of Chicago at night and indulge in the memorable nightlife with our guide…


Big names like Muddy Waters created a blues style that’s distinctly Chicagoan, and its memory lives on in the city’s blues clubs. One of the best streets to head for is Lincoln Park, where two blues clubs stand on opposite sides of the street. Kingston Mines hosts live music 7 days a week, and B.L.U.E.S. knows how to put on a great show too. Why not visit them both in one night?

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Craft beer has gained a cult of appreciators worldwide, so make sure you sample the delights of Chicago's craft beer scene yourself at the city's multitude of small, independent breweries. Located in Logan Square, Revolution Brewery is one of our favourite venues. A brewpub like no other you’ll find a warm and welcoming atmosphere, with mouth-watering charcuterie boards and around 20 great-tasting beers on tap.

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Chicago is the place where comedians Steve Carell, Tina Fey and John Belushi all launched their careers. So, as you can imagine, there’s a thriving comedy scene here. If you love improv and sketch comedy, then one of the best places to visit is The Second City. On most nights here the second act features scenes based on audience suggestions. So why not throw them some curveballs!

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Red Route, Stop: 360 Chicago


The Aragon has seen musical fashions come and go. Originally hosting big band music, the ballroom became famous as a venue for rock shows in the 60s and 70s, and then punk took over, with Nirvana, Green Day and The White Stripes all recording live albums here. Check out the local press when you arrive to see what bands are playing – you might just catch an awesome night.

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Orchestra Hall on Michigan Avenue has been home to the Chicago Symphony Orchestra since 1904. Thanks to the devoted hard work of sound engineers, the acoustics here are perfect – from every single seat. So, whether you’d like to hear the orchestra in full flight, or catch whoever’s playing while they’re in town, it’s worth booking in advance.

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Red Route, Stop: Art Institute of Chicago


Chicago is where the world first heard house music, and that legacy lives on in venues like Smart Bar. The world’s best DJs choose to come and play here. And it’s no wonder why when you hear the Funktion One sound system - the sound quality has got to be heard to be believed. If you’re a fan of house or techno, you’ll want to dance your socks off here. Or if you fancy something more lowkey, come along on a weekday night to catch an indie DJ at a bargain price.

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A big space for some big sounds. There are two stories here, and if you come at weekends you’ll be able to dance and drink on both of them. Weeknights are when just the main floor is in action. It’s in the Fulton Market area of town and can get very busy, so we recommend arriving early to grab your place in the line.

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Red Route, Stop: Willis Tower & Skydeck Chicago


Ever wondered what a prohibition jazz joint was really like? Well come along to North Broadway and find out. The Green Mill feels like it’s been preserved from another era. Al Capone used to drink here, and the paintings on the walls hark back to its gangster past. Now it’s a haunt for well-dressed sophisticates keen for a classy cocktail.

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Most of the best spots to spend an evening are in Logan Square, Uptown and Lincoln Park, so hop on our Big Bus tours during the day to see all the sights and Chicago landmarks before heading over there when the sun sets. And if you can’t get enough of Chicago at night, then make sure you check out our top picks for the Best Bars in Chicago too!