Local experts share 13 unique things to do in Chicago that are guaranteed to help you get to know the real Windy City.
Chicago is well-known for many things from iconic foods, to the famous Cloud Gate (aka “The Bean”), to local art and culture. Whether you’re in the market for a home in Chicago, an apartment with a view, or a rental house in one of the many neighborhoods, The Windy City is ready to dazzle you with all it has to offer.
The Chicago Water Taxi comes recommended from local photographer Saverio Truglia Photography. “Perhaps one of the most unique and affordable ways to see Chicago. This unguided commute through the heart of the city offers breathtaking views of Chicago's skyline from a different perspective. Take it round trip or just one way.”
“It is a tradition for my team to grab an ice cream cone from Jeni’s Splendid Ice Creams after long wedding days. Not only do they make the craziest, most amazing flavors you could ever imagine, but they have mastered the classics,” shares Alyssa of Northwest Weddings, a Chicago-based wedding coordination and planning company. “We highly recommend heading to the Fulton Market location for great ice cream and great music in the heart of Chicago.”
One of the most unique things you can do in Chicago is simply strolling through the many neighborhoods of the city. Marissa, owner and wedding photographer at Marissa K Webb Photography says Chicago thrives on its neighborhoods, each corner of the city fostering its own vibrant community. “The West Loop, for instance, represents the perfect blend of the city's industrial past and its modern creative pulse. This is where spaces like the Little Goat Diner become more than just a restaurant—they transform into venues for celebration and connection.”
Photo courtesy of Bronzeville Winery
The Bronzeville Winery, known for its “cool vibe,” seamlessly blends art, culture, and community while offering an exceptional selection of food, cocktails, and wine accompanied by live entertainment. Whether you’re enjoying locally sourced food or sipping on wines highlighting the craft of female and minority winemakers, it’s a perfect spot to experience the rich history and vibrant future of Chicago.
Photo courtesy of Mirabella Italian Cuisine & Bar
Chef Arturo, originally from Ecuador, has called Chicago home since he was 20 years old. At his beloved restaurant, Mirabella Italian Cuisine & Bar, you’ll find family warmth, old-school Italian dishes, and the best-grilled calamari in town. Chef Arturo’s passion makes Mirabella a true Chicago gem.
There is something for every nature lover at The Peggy Notebaert Nature Museum. Located in the heart of Lincoln Park, Chicagoans of all ages can connect with the wonders of nature and science. Meet local turtles through animal encounters, experience the tropical free-flying butterflies and moths of the Judy Istock Butterfly Haven, and discover more amazing adventures the museum has to offer.
Make sure to check out New Book Joy “Booktique” and head to one of their monthly Mix + Mingle events for another unique activity to do in Chicago. Their gatherings provide a true taste of Chicagoland culture, from books and reading pairings to drinks, food, music, and more from small businesses. Swing by an open house to meet new people in the community and get a taste of their featured local businesses such as lobster rolls from Une Année, Old Bay Chips from Snack Lab, mini fruit tarts from Bee My Honey Sweets + Treats, and summer wine tastings from Bottles & Cans. They even have some bookish events coming up for kids to enjoy, too.
For a quintessential Chicago experience, visit The Blackstone Hotel, famously known as the 'Hotel of Presidents.' Built in 1910 with stunning Beaux-Arts architecture, this historic landmark has hosted presidents and celebrities alike. Located in the heart of the arts and theater district, it’s the perfect spot to immerse yourself in Chicago’s history while exploring nearby Millennium Park.
Since opening in late summer 2018, Le Sud Mediterranean Kitchen has become a favorite with Roscoe Village neighbors and friends from across the city and suburbs. Their spacious sidewalk cafe becomes fully enclosed in the winter season, giving guests an iconic outdoor dining experience from them year-round.
If you're looking for a unique cocktail experience, check out Golden Years in Chicago. This West Town cocktail bar offers the feel-good Rock and Blues of the 70s, along with modern takes on the fun cocktails of the day. They also offer a daily happy hour and the best Toki Highball in the city.
Just a quick Metra ride outside the city, the small-but-mighty Elmhurst Art Museum has a rotating exhibition schedule that compares to world-class museums and is situated on the gorgeous Wilder Park in the Elmhurst neighborhood, a sprawling and walkable outdoor retreat. While you’re on the museum campus, check out the McCormick House, an idyllic 1950s home design by the iconic 20th century architect Mies van der Rohe.
Chicago Prime Italian is a must-visit in the suburbs of Schaumburg. This family-owned gem offers comfort Italian fare made with fresh organic ingredients, house-made sauces, and pastas, alongside prime steaks, fresh seafood, and an award winning wine list. With a beautiful patio for seasonal outdoor dining and a welcoming atmosphere, it’s an ideal spot for any occasion.
Miguel of MNPhotoStudios recommends these beautiful places to visit for little or no cost:
From open-ended wanderings to personalized experiences, life in Chicago offers something for everyone. The vibrant and inclusive community makes it a great place to explore or put down new roots. No matter what brings you to the Windy City, these 13 unique things to do in Chicago are just the tip of the iceberg when it comes to this city.
Kaitlyn is a Content Marketing Coordinator with Redfin. She lives in Seattle, WA, where she enjoys hiking, reading, and finding cozy coffee shops to write in. Her ideal home has an in-home library with big windows for natural lighting to read by.