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Chicago may be famous for its eye-catching skyline and iconic deep-dish pizza, but the city’s true charm lies off the tourist path. Whether you’re an adventurer, a crafty soul, a foodie, or simply looking to relax, there’s plenty of unique things to do in Chicago, IL..
Whether you’re in the market to buy a home in the city, have your eyes on an apartment, or looking to rent a house in the area, you’ll soon find there’s plenty of unique things to do in Chicago. First-time visitors, new residents, and lifelong locals alike will discover hidden gems that make you fall in love with the Windy City.
1. Unleash your creativity
Chicago is renowned for its rich artistic heritage and vibrant art scene. Whether you’re looking to enrich your skills or just enjoy a creative escape, the city offers endless possibilities to foster your creativity.
Express your artistic skills
If you’re looking to enhance your art skills or indulge in a creative escape, head to The Paintbrush, a beloved art studio nestled in Lincoln Park where they offer art classes and events for kids as well as their After Dark adults program which has featured events like “Art and Wine Night” or “Sip and Slime.”
Try your hand at street art
Always admired street art and wish you could try it yourself? Head to The Studio W.I.P in Uptown, where you can dive into the world of street art through their hands-on Spray Paint workshops. If you prefer to appreciate the art from afar, join a Chicago street art tour and explore the vibrant murals around the city. Gabby at The Studio W.I.P shares, “the perfect way to end your night is with some prime hole-in-the-wall pizza at Gigio’s Pizzeria.” Here, you can expect to satisfy your taste buds with classic and satisfying traditional pizzas.
Experiment with different mediums
Not an artistic person yourself but have a little one who wants to explore their creativity? Easel Art Studio, located in Ravenswood and Bucktown, offers all avenues of art including classes like Food Art, Printmaking, and Portfolio Lab. Each class is focused and led by talented instructors who ignite every child’s imagination and encourage artistic freedom.
2. Serving sports beyond the stadium
Chicago is a city that lives and breathes sports, but the action isn’t limited to just watching from the stands. For those eager to get in on the excitement, the city offers hands-on experiences that go beyond the ordinary, catering to both adrenaline seekers and casual enthusiasts.
Hit the slopes year-round
Check out Snowlike Studio, the only indoor ski and snowboard spot in the area. Located in Schaumburg, IL, this unique venue offers a chance to hit the slopes year-round, whether you’re a beginner or a pro, young or old.
Photo courtesy of Snowlike Studio
Eat, drink, and swing
For an unforgettable game night, head to The Barn Hockey Bar and savor a chef-driven menu with friends, sip on ice-cold beverages, and enjoy nonstop fun in a lively atmosphere. Need a break from the action? Swing by the “Gilmore Room” in the back, featuring two state-of-the-art golf simulators for some friendly competition between periods.
The pregame before the game
Start your pre-game adventure just a short walk away from the ballpark at Café Tola on Southport. You can enjoy Chicago’s best empanadas and horchata lattes in a vibrant setting that gets you ready for the exciting game ahead. This beloved café provides the perfect on-the-go snack before you make your way to Wrigleyville for a Cubs game.
3. Take your taste buds on an adventure
Chicago’s food culture is a colorful tapestry of flavors and experiences. The city blends diverse culinary traditions with local innovation, offering a dynamic array of dining options that cater to every palate and occasion.
Sip and savor with friends
Located in two Chicago locations, get a feel for the cool industrial energy at Fulton Market or the history charm meets modern artistic vibe at Logan Square when visiting Federales Bars for a bite to eat. “If you’re new to the city, you have to try Federales,” Tonia Rudny at Feed Media shares, “both locations offer tasty margaritas, handmade taquitos, Chicago’s best guacamole, and 15+ creative tacos. Plus, monthly specials, a great happy hour, and a weekend brunch you can’t sleep on.”
If a sports game and live music is more your speed, head to Joe’s Bar on Weed St. This six-time Academy of Country Music Award winner for Nightclub of the Year, has been the go-to place for both local and touring country acts for 27 years. Not only is it a music hotspot, Joe’s is also one of the city’s largest sports bars, featuring alumni and fan clubs for teams like the Carolina Panthers and the Pittsburgh Steelers.
Photo courtesy of Federales Bar
Experience global flavors
Satisfy your craving for a European vacation at Cafe Cremerie, where the flavors and ambiance of Europe come to life. This charming spot invites you to indulge in exquisite sweets, savory bites, rich, smooth coffee, and a curated selection of wines—all set within a warm, inviting atmosphere that transports you straight to the heart of Europe, no passport required.
Continue your global culinary journey at ROOH, one of Chicago’s top modern Indian restaurants. Known for blending authentic flavors with unexpected local ingredients, ROOH offers a dining experience that’s both innovative and true to its roots. Don’t miss their new tasting menu, crafted in collaboration with a Michelin-starred chef from the Netherlands, for a promising fusion of international tastes.
For a touch of Ireland without leaving the city, get up early on the weekend for a rugby or Premier League match at Mrs. Murphy’s. Enjoy a full Irish breakfast at this imported Irish bar, complete with an authentic pub experience. If you’re not into pints or whiskey, join the lively music session, sign the kids up for Irish music lessons, or pick up imported Irish chocolates, biscuits, and sausages from the shop.
Fine dining lovers
For an approachable fine-dining experience, Boka is a must-visit Michelin-starred restaurant located in the heart of Lincoln Park. With a stunning main dining room, a cozy patio, and a bar serving delicious handcrafted cocktails, Boka offers an elevated yet welcoming atmosphere that makes every visit special.
4. Feel the buzz of live entertainment
If you’re in need of a good laugh, KOVAL Comedy at Chicago Comedy Works delivers both top-notch stand-up and specialty cocktails. Each show features some of Chicago’s best comedians, and to make it even better, all proceeds benefit a local nonprofit partner for the night. Whether you’re rounding up friends or flying solo, it’s the perfect way to enjoy an evening of laughter and support the community.
5. Discover local treasures
Chicago is a shopper’s dream for finding unique and eclectic items. With its rich vintage scene, the city offers a range of opportunities to discover distinctive pieces, from rare antiques and one-of-a-kind home decor to hidden literary gems.
Time travel through vintage finds
For a rotating shopping adventure, check out the Vintage House Chicago pop-up, perfect for all your thrifting needs. Popping up twice a month at different city locations, Vintage House features a mix of vintage and handmade vendors, offering everything from 1920s pieces to Y2K styles.
If home decor for your new home is what you’re after, look no further than Vintage Grind House. Located in Chicago’s Irving Park area, explore one of the largest collections of truly eclectic vintage furniture including chairs, sofas, lighting, art and one-of-a-kind knick-knacks. Be prepared to spend hours browsing through turn of the century antiques, mid century modern, post modern, contemporary furnishings and everything in between.
Photo courtesy of Media Meade (@oppungo) | Vintage House Chicago
For the bookworms
For an intimate literary escape, visit Tangible Books at 3326 S. Halsted. This cozy shop caters to Chicago’s literati and book lovers, with owner Bob always on hand to chat and help you discover your next great read. Don’t miss their periodic events, like the poetry readings and open mic nights hosted by Vittorio Carli every first Saturday of the month. Plus, if you’re looking to declutter your bookshelves, Tangible Books offers a convenient way to recycle your reads.
6. Explore Chicago from every angle
Taste the history
While you’re exploring Chicago’s diverse neighborhoods and soaking in the local culture, taking a Chicago Foodways Tour is another great step to deepen your connection with the city. The tours highlight the stories of Chicago’s immigrant communities and the delicious cuisines they’ve brought with them, from the hidden gems of Andersonville to the vibrant flavors of Uptown and Lincoln Square. It’s a perfect way to experience the city’s global culinary landscape while learning about the people who shape Chicago’s cultural fabric.
Uncover the dark secrets
Dig into the dark side of Chicago’s history with the thrilling Gangsters and Ghosts Tour. This unique experience blends history and mystery as you walk through the same streets once ruled by notorious mobsters like Al Capone. Expert guides will share chilling stories of power, crime, and the supernatural while you visit haunted landmarks that vividly bring Chicago’s dark past to life.
7. Set sail
To truly experience life in Chicago, take it in from the other side of Lake Shore Drive with KnockOut Charters. Whether you’re cruising to Soldier Field for a Bears game, enjoying a sunset cruise after dinner on the river, exploring the skyline on a private architecture tour, or relaxing in the playpen with your friends, taking a ride on the water offers a unique and unforgettable way to explore the city.
Unique things to do in Chicago, IL: Final thoughts
Chicago is a city that thrives on its diversity, offering an array of experiences that go beyond the typical tourist stops. Whether you’re just in the beginning phases of thinking about moving to Chicago or you’re a lifelong resident, there’s something for everyone. you’re exploring local art scenes, trying new sports, indulging in the city’s culinary offerings, or unearthing vintage treasures, there’s always something unexpected to discover.
Source: rent.com