Things to do in Uptown, Chicago

UPDATED JULY 2024
By Dom Bewley
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.

Including

  • 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!

Dom Bewley
Go City Travel Expert

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Things to do in Gold Coast, Chicago

So, you've chosen your vacation destination. The Windy City. Chi-Town. The real-life Metropolis, minus the superheroes. Chicago is a fantastic getaway destination, full of great food, fun nights out, and plenty of top-level entertainment. But it's a big old town, with multiple districts and areas that crisscross throughout its gargantuan layout. With so many to choose from, which one is right for you? Well, don't let choice paralysis get the better of you! We've done all the research necessary, so you don't have to. Give Gold Coast a go. It's as simple as that. With a wealth of entertainment on offer, it's the perfect vacation spot. Here are our picks for the best things to do in Gold Coast, Chicago! Including: Oak Street Beach Playboy Mansion Broadway Playhouse Washington Square Park Drake Hotel Bar and more! Hit the Beach Why not ease into your trip with a spot of lounging? After all, you've got the rest of your vacation to go see the sights. Lucky for you, the Gold Coast lives up to its namesake. Head there, and you'll find Oak Street Beach. Of course, you'll find heaps of golden sand, clean sea, and (hopefully) glistening sun - that's what the beach is all about, after all. However, Oak Street Beach is also perfectly placed to visit at any time during the day, as it's just a stone's throw from the city itself. Take a dip in the ocean, go grab an ice cream for the kids - or yourself, who are you kidding - and then check out the nearby patio bar for a cool, refreshing drink. Easily one of the best things to do in the Gold Coast when you visit Chicago. Feel like a Playboy Yes, really. Though you probably know the Playboy Mansion as the once celebrity-laded party mansion near Beverly Hills, it wasn't always there. In fact, the original Playboy Mansion was bought right here on the Gold Coast back in the '50s. The rather less impressive original is well over 100 years old at this point, and has changed hands multiple times. First, Hefner donated it to the School of the Art Institute of Chicago when he moved into his legendary LA pad. Then, the institute sold it to a redevelopment firm, and it's now been converted into condos in a rather typical fashion. However, if you want to see a piece of 20th-century American history in the flesh, you owe it to yourself to go and bask in the extravagant opulence of the original Playboy Mansion. Just don't plan on buying one of the condos, unless you've got a few mill to spare. Broadway, baby! If the weather takes a turn, or you just want a couple of hours out of the sun, why not retreat to the bright lights and comfort of broadway? Yes, even in Chicago, you can get a taste of the New York performance mile thanks to Broadway Playhouse! A stone's throw from the coast, you'll find a host of great plays and musicals being shown throughout the year, from all-time classics to the new shows on the block. You might even stumble upon a one-man show, or local play before it gathers steam. Walk in the Park Are you a fan of the color green? Do you like walking? Is the prospect of breathing in fresh air, mingling with trees, shrubs, and grass appealing to you? Answer us these questions three, and we'll give you a place you want to be. At. A park, of course! Gold Coast has you covered in flowers and grass, thanks to Washington Square Park. Go there for the giant 19th-century fountain, stay for the delightful green spaces, picnic opportunities, or simply for a stroll. So, what are you waiting for? Get Risky When you're in Gold Coast, why not grab a drink at a Hollywood monument? Sort of, at least. Featured in the '80s Tom Cruise classic Risky Business, the Drake Hotel is one of Chicago's most recognizable landmarks! But we're not talking about the room service here. We're talking about the Hotel's bar, called the Coq d'Or. This lavish hotel lounge has been warming customers' cockles since the dark Prohibition days. Head inside and find a wealth of drinks, a menu to die for, and enough comfort you'll feel like a marshmallow. A pampered marshmallow. Best Pizza in town Wow, all that doing things, seeing things, and experiences must have made you hungry. Well, Chicago is famous for one thing in the food department, and that's deep dish. The Chicagoan take on the Italian classic is known worldwide for its deliciousness, thanks to its unusual sauce-over-cheese twist. So why not go get some and see if it lives up to its reputation? Lou Malnati's, right in Gold Coast, is arguably the best in town. The name is a staple of the Chicago style, having helped pioneer it in the early 20th century. So go grab a slice of delight and take your tastebuds to pizzatown. Or something. Go Shopping Let's end this list on a shopping, surely many of our readers' favorite pastimes. Thankfully, Gold Coast is full of shops of all shapes and sizes, so no matter what item you seek, you're sure to find it there. However, for those of you with expensive tastes, you'll be looking for The Magnificent Mile. Head there, and you'll find a shopper's paradise. Over 400 stores line the 'Mile', including the likes of Chanel, Louis Vitton, and Tiffany. So, if you're looking for some dear deals and have the cash to splash, you'll be right at home. On top of all that shopping, you'll also find a slew of gourmet restaurants, snug cafes, and much more. So, if that all sounds like heaven to you, go on down and see what's cracking! And that's our list of the best things to do in Gold Coast, Chicago! If you want to know about the other areas of Chicago, check out our thoughts here. Heading to Chicago at the tail end of winter? The beaches might be a no-go, but there's plenty more to do and see!
Dom Bewley
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Thanksgiving in Chicago

Spending time with friends and family in Chicago for Thanksgiving this year? Check out these suggestions for local activities and more seasonal things to do in November.
Katie Sagal
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Things to do in Pilsen, Chicago

Do you like your neighborhoods to have the perfect mix of cool, community, and culture? Then give Pilsen a go! This district of Chicago has some great and unique entertainment opportunities for travelers and locals alike. So, if you're visiting Chi-Town on vacation, these are the best things to do in Pilsen! Including Live music BBQ with a glamorous twist Some culture Parks Street art and more! Get live We begin today with music. Live music, to be exact! Nothing quite beats seeing a band jam in the flesh, and lucky for you, Pilsen has a few awesome venues to check out. One of Pilsen's oldest landmarks is Thalia Hall, which is over 120 years old and still going strong! This powerhouse of live entertainment hosts comedy greats like Dave Chappelle as well as huge bands like The Smashing Pumpkins, among many others. In recent years, the addition of several bars, restaurants, and alternative stages have grown Thalia Hall's entertainment opportunities. So go check out what's on when you're visiting Chicago. If you prefer your music noisier, your performance wilder, and your gigs more carefree, then check out The Dojo. Chicago's premier underground music venue hosts local noise bands, leftfield artists, and much more. Every weekend they have new and exciting alternative acts gracing the stage, so head down there and see what all the fuss is about! Carnival BBQ BBQ is the backbone of America. For decades, we've ventured out of our abodes, fired up the grill, and invited friends and family over for a cookout. Nothing brings the community together better than BBQ. And Pilsen has a quality BBQ joint with a musical twist. We're talking about Honkey Tonk BBQ, where hungry souls can go to fill their bellies and their minds, thanks to the jazz and blues parties they host most nights. Chow down on some delicious BBQ meat, and then work off the calories through the night. But one Saturday a month, they mix things up a bit, as the place is taken over by an improv burlesque quintet. They'll have you dancing and laughing in no time. Easily one of the best things to do in Pilsen when you visit Chicago! Get cultural Next, let's switch gears to something more cultural. If you're looking for some inspirational, mind-opening experiences, then Pilsen's got you covered. At the National Museum of Mexican Art, you'll find art from Mexicans both in the US and across the border. Chicago is known as the 'Mexico of the Midwest', and this museum is a testament to the artistry of many Mexicans who now call Chi-Town home. Wander through over 7000 pieces, and learn about the stories that helped create them. Or, if your tastes lie a little leftfield and you want something exclusive, then House of the Apocalypse might be just what you're looking for. Only open for four hours every month, this weird and wonderful collection of artwork is quite the sight. Featuring sci-fi and post-apocalypse influences, House of Apocalypse's collection is something you won't quite find anywhere else. Street art named desire If you prefer your artwork of the outdoor, urban variety, or simply want to peruse in the glow of the sun, then go check out the massive collection of street art on 16th Street. Brought together thanks to a collaboration between multiple local institutions, you'll find a wealth of works from global street artists. In fact, this collaboration has helped restore a lot of the area, which was once derelict and dirty. So, two birds with one stone then! At the same time, it's ensured that Pilsen remains true to its roots, and doesn't sway too far into the gentrification we've seen happening all over America and other parts of the world. Pilsen is community-first, and always should be. More eateries! And when all that activity brings on the hunger prangs, Pilsen's got some great restaurants to sate your grumbling tummy. Head to Barrio for some authentic Mexican cuisine and a whole menu dedicated to tequila-based cocktails! What some fresh, farm-to-table dishes at a reasonable price? Go check out Dusek's Tavern. Their fixed menu of exciting, New-American cuisine means you get delicious food and a great price. In the market for some delicious East-Asian delights? Give HaiSous Vietnamese Kitchen a look. With a mix of street food, fixed dishes, unique family recipes, and a fine line of cocktails to boot, it's a must-visit for anyone visiting Pilsen. Drinks After all of those activities and food, the next stop on your Pilsen journey should be one of its many watering holes. Thankfully, Pilsen is full of them, so you have the pick of the litter. Want some classic pub food, refreshing craft beer, and cool aesthetic on your night out? Skylark's the one. Want to try something a little kookier? How does a hidden basement bar with creative punches sound? That's Punch House, which has a whole menu full of fruity punches to try, as well as sandwiches, all rolled into a retro-vintage vibe. Doesn't get more Pilsen than that! Or, grab a slice of pizza and pick from any number of craft beers at The Green Room Tap. Whichever way you decide to go, you're bound to have a blast! Find a park-ing spot Let's end this list on a walk through some of Chicago's green and pleasant land. Of course, we're talking about parks. And, of course, Pilsen's got its share of great ones! Firstly, there's Harrison Park, which has a gym, indoor pool, and even meeting rooms housed within the Fieldhouse. So, if you like to get active, you can do it inside or out. Beyond that, you'll find over 18 acres of sweet green space to go sit, have a jog, or prepare a picnic. Look out of the bust of Emiliano Zapata, one of the biggest names of the Mexican Revolution. Or, check out Dvorak Park, which boasts a baseball field, its own pool and unique water feature, soccer pitches, playgrounds, and a whole heap of comfortable, welcoming grass. You may even catch the odd performance there on the right day, as there's a big art scene that calls the park home. The playground is perfect for kids, if you're bringing the little ones. And that's our list of the best things to do in Pilsen, Chicago!
Dom Bewley

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