Chicago, the Windy City, is a dynamic destination brimming with culture, history, and stunning architecture. Whether you’re an art lover, foodie, or adventure seeker, this city offers an endless array of attractions. To make the most of your first visit, here’s a detailed guide to 12 must-do activities in Chicago that will leave you in awe of this vibrant metropolis.
1. Stroll Along the Chicago Riverwalk
The Chicago Riverwalk is a scenic oasis that stretches along the Chicago River, offering breathtaking views of the city’s world-renowned architecture. This pedestrian-friendly walkway is perfect for a relaxing morning or afternoon stroll. Stop by the waterfront cafes, take a kayak out on the river, or simply enjoy people-watching as the city bustles around you. Don’t forget to snap photos of iconic buildings like the Marina City Towers and the Wrigley Building while you’re here.
2. Take an Architecture Boat Tour
No trip to Chicago is complete without an architecture boat tour. Chicago is celebrated as the birthplace of the skyscraper, and the best way to admire its towering structures is from the water. Expert guides will walk you through the stories behind landmarks like the Willis Tower and Tribune Tower, sharing the history and innovation that shaped this urban landscape. Whether you take a daytime cruise or a sunset tour, this is one experience you won’t want to miss.
3. Wander Through Millennium Park
Millennium Park is much more than just the home of “The Bean” (officially named Cloud Gate). This expansive park is a cultural hub, featuring impressive public art, beautifully manicured gardens, and lively events. Take a leisurely walk through the Lurie Garden, enjoy the whimsical Crown Fountain, or catch a free outdoor concert at the Jay Pritzker Pavilion during the summer months. It’s a vibrant spot to soak in the city’s artistic spirit.
4. Marvel at the Art Institute of Chicago
Ranked among the best art museums in the world, the Art Institute of Chicago is a treasure trove of masterpieces. It boasts an impressive collection of works from every corner of the globe, including van Gogh’s The Bedroom and Georges Seurat’s A Sunday on La Grande Jatte. Be sure to explore its modern wing, designed by Renzo Piano, which features contemporary works and offers stunning views of Millennium Park. Allocate at least a few hours here to truly appreciate its vast collections.
5. Soak in Skyline Views at Skydeck Chicago
Skydeck Chicago, located on the 103rd floor of the Willis Tower, is a must-visit for breathtaking city views. The star attraction here is The Ledge, a glass-floored balcony that extends four feet outside the building, offering a thrilling perspective of the bustling streets below. On a clear day, you can see up to four states from this vantage point. It’s a fantastic spot for photos and an adrenaline-pumping experience that’s uniquely Chicago.
6. Try Chicago’s Famous Deep-Dish Pizza
When in Chicago, indulging in deep-dish pizza is non-negotiable. This hearty, cheesy dish is a local staple that has gained international fame. Head to iconic spots like Lou Malnati’s, Giordano’s, or Pequod’s to savor this gooey delight. With its buttery crust, generous layers of cheese, and rich tomato sauce, one slice is often a meal in itself. Pro tip: pair your pizza with a crisp local beer for the ultimate Chicago food experience.
7. Explore Navy Pier
Navy Pier is a family-friendly destination that combines entertainment, dining, and stunning views of Lake Michigan. Originally a shipping facility, this iconic landmark now features attractions like the Centennial Wheel, the Chicago Shakespeare Theater, and the Crystal Gardens. Take a leisurely ride on the Ferris wheel for panoramic views of the lake and city skyline, or enjoy a lakeside meal at one of its many restaurants. It’s the perfect spot to spend an afternoon.
8. Take in a Show at The Chicago Theatre
The Chicago Theatre is more than just a stunning photo op with its iconic marquee; it’s a cultural gem that offers an unforgettable entertainment experience. This historic venue has hosted legendary performers and features a grand, French Baroque-style interior that will leave you in awe. Check their schedule ahead of your visit for concerts, comedy shows, or theatrical performances. Even if you don’t attend a show, a guided tour of the theater is well worth it.
9. Visit the Museum of Science and Industry
The Museum of Science and Industry is one of the largest science museums in the world, making it a must-visit for families and curious minds. Interactive exhibits like the Science Storms gallery and a real German U-Boat offer a hands-on learning experience. Don’t miss the model train that spans a detailed mini-version of the U.S. or the underground coal mine tour for a fascinating look into industrial history.
10. Spend a Day at Lincoln Park Zoo
Nestled in the heart of one of Chicago’s most beautiful neighborhoods, Lincoln Park Zoo is a free attraction that’s perfect for animal lovers. Home to species from around the globe, including polar bears, zebras, and gorillas, the zoo also boasts gorgeous landscaping and views of the Chicago skyline. It’s an excellent place to spend a leisurely afternoon without spending a dime.
11. Catch the View from 360 Chicago Observation Deck
Located on the 94th floor of the John Hancock Center, the 360 Chicago Observation Deck offers jaw-dropping views of the city and Lake Michigan. Thrill-seekers can experience Tilt, a moving platform that tilts you outward for a unique, heart-pounding perspective. The observation deck is particularly magical at night when the city’s lights create a sparkling canvas beneath you.
12. Walk Along the Lakefront Trail
The Lakefront Trail is an 18-mile stretch of pure bliss for walkers, bikers, and joggers. This path offers unparalleled views of both the city skyline and the shimmering waters of Lake Michigan. Start at North Avenue Beach and make your way south to soak in some of the city’s most picturesque spots, including Grant Park and the Museum Campus. The fresh breeze off the lake makes this an invigorating way to experience Chicago’s natural beauty.
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Final Thoughts
Chicago is a city that offers a perfect blend of culture, history, and modern energy. By hitting these 12 must-see attractions, you’ll experience everything that makes the Windy City so unique. From the architectural wonders to the culinary delights, Chicago guarantees memories that will last a lifetime. So lace up your walking shoes, pack your appetite, and get ready to explore one of America’s greatest cities. Safe travels!
