things to do in uptown chicago

Things to do in Uptown, Chicago

Heading to Chicago for your vacation? Why not check out Uptown? There's heaps of entertainment on offer, so make sure you see as much as possible! Here's our guide to all the best bits.


  • Eastern delights
  • Sun, sea, and sand
  • Street Art
  • A boozy visit
  • Starlit shows
  • and more!
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Argyle Street

Let's start things off with a shopping extravaganza. Uptown's got some fantastic spots, but we want to focus on one that's rather unique. Head to Argyle Street, and you'll feel like you've been transported to a completely different place. But why is that? Well, it's because countless Vietnamese, Thai, and Cambodian businesses call it home. Colloquially referred to as 'little Vietnam', this pedestrian-friendly area has tons to see and do. Take a stroll and find plenty of unique produce to whip up your own Asian masterpieces, or simply buy it from the experts at many of the food stalls and restaurants. Looking for some interesting pieces for your home, or accessories to adorn your body? There are a wide variety of clothing, plant, and knickknack joints that'll tickle your fancy and then some.

The beach

Sometimes, we all need a little sun, sand, and sea in our lives. Nothing quite lifts the spirits than a trip to the beach, especially when the sun is sizzling in all its glory. Well, Uptown's got you covered, thanks to Montrose Beach. It's Chicago's biggest beach at over 56,000ft squared, and you'll find plenty of food, drink, and fun within a stone's throw of your bathing spot. Hire some equipment and enjoy some watersports, relax under the sun (and plenty of sunblock), or go take your dog for a walk in the pup-friendly area. Easily one of the best things to do in Uptown if the weather's good.

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Street Art

If you're the kind of person who has their head turned by street art, you're in luck. Chicago is brimming with murals and pieces all over the city. And yes, while some are admittedly better than others, you don't even need to go looking. Instead, head to the Clifton Avenue Street Art Gallery, where you'll find a curated mix of pieces from all over the world, including some from Chicago natives. Ideal for those of you looking to increase your follower account. We know that's important to some of you.

Distill Chicago-style

Do you like spirits? Not ghosts, the other kind. The kind you sip with class, or slam down with reckless abandon. Yes? Yes, of course you do. Well, have you ever wondered where those spirits come from? Sure you have. If you want to see the process in action, especially for local craft brewers, head to Koval Distillery in Uptown. See how this local husband-and-wide duo, who've been crafting their own take on spiritual classics for nearly 15 years. You'll see how they've upped their production to serve a long list of customers both in Chicago and further afield, and how they've grown to accommodate gin, whiskey, and other liqueurs. Go tour the premises, pick up some for yourself, or stick around for a cocktail class.

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Nights out with style

If you're looking for a fun night out, Uptown has a lot on offer. There's tons of places to wet your whistle, but why not combine your night out with some great live music?

Carol's Pub is half a century old, and still going strong. It's a no-nonsense place where you grab a beer and a bite, or sample the revamped cocktail menu. However, every weekend they have three days of live music, with bands playing on Friday and Saturday, and a karaoke night on Sunday to help you end the week on a high before the Monday blues creep in.

Or, for a bit more of an upmarket vibe, check our Green Mill Cocktail Lounge. For over a century, it's been the city's go-to place for the Chicago jazz scene. Even infamous Chi-Town gangster Al Capone frequented it back in the dark Prohibition days. You can even grab his booth, if you're lucky. Inside, you'll sip fine cocktails and nod your head to a wide variety of live performers in the jazz community. They even host slam poetry nights, if that's your scene.

Looking for more modern music? Check out Riviera Theatre, an old cinema that now showcases an eclectic mix of indie rock, rap, and DIY punk acts throughout the year. Plenty of up-and-coming Chicago acts take the stage every week, so if you're looking for your next favorite song, head down and see what's cracking.

Whichever place you choose, your night out will be one of the best things to do in Uptown when you visit Chicago!

Catch a show or two

Looking for a spicier night out? Don't you worry, dear reader. We've got some spicy samples that are guaranteed to hit the spot.

Having recently moved across town from River North, the Baton Show Lounge now calls Uptown home. This hyped spot has hosted some of the biggest drag acts around, including Ru Paul and Madonna, among a long list of luminaries. Every night, you'll find a different act taking to the stage, giving it their all, and getting the crowd involved.

Or, for a more varied cast of acts, check out Kiss Kiss Cabaret. Every week, you'll find a great burlesque, vaudeville, or magic show unfurling before your very eyes. Grab a drink, take a seat, end drink it all in.

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Pay your respects

And finally, let's end this list with one of Uptown's most beautiful places. Graceland Cemetery might sound slightly morbid, but it's anything but. For approaching 200 years, it's been the final resting place of many of Chicago's most notable residents through time. Take a stroll and see if you can find the tomb of William Hulbert, who helped create the baseball National League, or famed film critic Roger Ebert. Alongside this monument to Chicagoans, you'll find plenty of trees and green space where you can go and relax after a long day, or bring a picnic during your vacation. A must-visit, and easily one of the best things to do in Uptown when you visit Chicago.

And that's our list of the best things to do in Uptown, Chicago!

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