Named after the elevated train tracks that encircle the central business district, the Downtown Chicago Loop is a hub of cultural, architectural, and culinary wonders. Whether you're a local looking for new experiences, a visitor searching for the best things to do in downtown Chicago, or a a foodie ready to join our Gateway to The West Loop Food Tour, here are 17 must-do activities in this iconic neighborhood.
Start your adventure in the heart of the Loop at Millennium Park, a 24.5-acre urban oasis that houses the world-famous Cloud Gate, affectionately known as "The Bean." Stroll through the lush gardens, admire public art installations, and if you're visiting during the summer, catch a free concert or movie at the Jay Pritzker Pavilion.
Chicago is world-renowned for its architecture—after all, we did invent the skyscraper! But it can be hard to navigate the urban maze to properly appreciate the skyline from ground level. It's best to have a guide. Enter Chicago Food & City Tours' premier offering: Buildings and Bites. This 2.5-hour stroll takes you through the Loop's main architectural corridor, covering the inside history of the Monadnock all the way to Willis Tower. The best part? It’s the only architecture tour that stops for a tasty, sit-down lunch!
Art lovers won't want to miss the renowned Art Institute of Chicago, home to masterpieces by Van Gogh, Monet, and Picasso. Don’t forget to dip down to the lower level for the Thorne Miniature Rooms. This amazing collection features 68 shoe-box-sized rooms reflecting historical settings from across the globe.
Discover the city's rich heritage aboard a relaxing river cruise. Knowledgeable guides will regale you with stories about Chicago's most famous buildings, including the Willis Tower and the St. Regis. At only 90 minutes long, it’s one of the essential things to do in downtown Chicago for any first-time visitor.
Most cities are known for a single dish. Chicago has a Mount Rushmore of invented eats: Deep Dish Pizza, Italian Beef, Chicago-style Hot Dogs, and Garrett Popcorn. Want to taste them all in one afternoon? Chicago Food & City Tours has you covered with the Iconic Foods of Chicago Tour. You’ll eat the whole Mount Rushmore of Chicago foods in one outing, with a bonus classic for dessert!
Learn more about the best pizza in Chicago from deep dish, to thin crust and more.
For an adrenaline-pumping experience, head to the Skydeck in the Willis Tower. Step onto "The Ledge," a glass balcony extending from the 103rd floor. Even if heights make you nervous, the 360-degree views of the sprawling Second City are worth the admission alone.
Admire the stunning architecture of the Chicago Cultural Center, which hosts free art exhibitions and concerts. Be sure to head to the top floor to see the Tiffany Dome, the largest Tiffany stained-glass dome in the world, restored to its original 1897 splendor.
Escape the hustle and bustle at Grant Park, known as Chicago's "front yard." Take a leisurely walk, have a picnic, and enjoy the water show at Buckingham Fountain, which remains one of the largest fountains in the world.
Explore the Chicago Riverwalk, a lively pedestrian path along the south bank of the river. You can dine at waterfront restaurants like Beat Kitchen or grab a local brew at Chicago Brewhouse. If you're feeling adventurous, you can even rent a kayak for a unique perspective of the skyscrapers.
Immerse yourself in classical music with a performance by the internationally acclaimed Chicago Symphony Orchestra at Symphony Center. Frequently named one of the best orchestras in the world, they deliver a world-class experience every time.
Catch a Broadway-quality show at the historic Chicago Theatre or the James M. Nederlander Theatre. Between massive touring productions and local premieres, the "Broadway in Chicago" scene is always buzzing with talent.
Perfect for families, Maggie Daley Park offers a rock-climbing wall, mini-golf, and a whimsical playground. In the winter, the Skating Ribbon is a top-tier activity, winding through the park's snowy landscape.
Explore the diverse array of art galleries along the Riverwalk, showcasing works by local artists and photographers. One piece, The Radiance of Being, sheds light on the city's art deco architectural past. And if the Riverwalk isn't enough art for ya, check out the scene in nearby River North, the neighborhood with the densest collection of art galleries in the U.S. outside of Manhattan. Plus, it is a great place to cap off the night with a cocktail! Check out our guide to the best bars in River North to learn more.
For a unique art experience, head to the Riverwalk at night to see ART on THE MART. This is the largest permanent digital art projection in the world, using the 2.5-acre facade of the Merchandise Mart as its canvas. It’s a spectacular, free way to enjoy the downtown atmosphere.
Discover the hidden underground walkway system known as the Pedway. Connecting dozens of buildings in the Loop, it's the best way to navigate downtown during inclement weather. Many visitors (and locals!) don't even know it exists, making it a true hidden gem activity.
While located just north of the Loop in Lincoln Park, this museum offers the best insights into how Chicago became the powerhouse it is today.
Pro Tip: After learning the history, head back downtown to join a Chicago Food & City Tours walk to see that history in person! Check available tour dates.
Experience the skyline from water level. Embarking on a guided kayak tour allows you to paddle through the heart of the city while learning about the engineering marvels that reversed the Chicago River.
The Downtown Chicago Loop is a treasure trove of activities and attractions, catering to every interest and taste. Whether you're into art, architecture, culture, or simply want to soak in the vibrant atmosphere of the Windy City, these 15 activities are bound to create lasting memories of your visit to this iconic neighborhood.
One of the newest and most immersive things to do in downtown Chicago is Flyover. Located right on Navy Pier, this multi-sensory flight attraction uses a massive 65-foot spherical screen and flight-motion seats to let you soar over the city. You’ll dive through skyscrapers, skim the surface of Lake Michigan, and experience the city’s iconic festivals and neighborhoods from a bird’s-eye view. It’s a high-tech way to see the architecture you learned about on your Chicago Food & City Tours walk from a completely different perspective!
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