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 and places to see, 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 at one of the top places to see 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.
Millennium Park At a Glance
Step into Chicago's rich Chinese culinary heritage on a top-rated food and culture walk through Chinatown. Chicago Food & City Tours offers a 3-hour, guided Chinatown Adventure Food Tour where you'll feast at five authentic restaurants. Savor everything from Hong Kong dim sum and spicy Szechuan specialties to sweet milk egg tarts. As you wander through the vibrant streets and hidden alleys of both Old and New Chinatown, your expert local guide will share fascinating insider stories of the neighborhood's history, landmarks, and traditional dining customs. Come hungry and leave with a deeper appreciation for the rich culture and diverse regional flavors that define Chinese cuisine!
Chinatown Food Tour At a Glance
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.
Art Institute of Chicago At a Glance
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.
Chicago Architecture River Cruise At a Glance
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!
Iconic Foods of Chicago Tour At a Glance
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.
Skydeck Chicago At a Glance
Admire the stunning architecture of the Chicago Cultural Center, one of the most remarkable free places to see in the Loop, hosting 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.
Chicago Cultural Center At a Glance
If you're looking for iconic outdoor places to see in downtown Chicago, 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.
Grant Park & Buckingham Fountain At a Glance
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.
Chicago Riverwalk At a Glance
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.
Chicago Symphony Orchestra At a Glance
Catch a Broadway-quality show at the historic Chicago Theatre. Between massive touring productions and local premieres, the "Broadway in Chicago" scene is always buzzing with talent.
The Chicago Theatre At a Glance
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.
Maggie Daley Park At a Glance
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.
Chicago Riverwalk Art Galleries At a Glance
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.
The Pedway At a Glance
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.
Chicago History Museum At a Glance
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.
Wateriders Chicago River Kayak Tours and Rentals At a Glance
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!
Flyover Chicago At a Glance
You Might Also Like
Best Things to Do in Chinatown Chicago: 21 Restaurants & Attractions
18 Things to Do in Chicago's Gold Coast Neighborhood & Why You Must Visit
12 Romantic Things to Do in Chicago to Impress Your Better Half
