Things To Do in Chicago For A Memorable Trip

Are you ready to go beyond the deep-dish pizza and skyline selfies? If yes, then get ready to dive into things to do in Chicago that reveal the city's true heartbeat, like its hidden alleys, unforgettable experiences and many more. Imagine starting your day sipping rich coffee at Pilsen's colorful street-art district, then slipping into a tucked-away jazz club and many more. And this is just the tip of the iceberg when it comes to the tourist things to do in Chicago that will make you feel like a local.

Book your flights to Chicago now and enjoy these 5 best things to do in Chicago to have the best time of your life.

Top 5 Things To Do in Chicago For An Unforgettable Adventure

1. The 606 Bloomingdale Trail

The very first things to do in Chicago when you are in the city is to explore this vibrant elevated greenway connecting 5 neighborhoods from Bucktown to Humboldt Park. The place is ideal for activities like walking, cycling, running and many more. The trail features wide concrete paths, benches, periodic rest areas and drinking fountains. Pause at fitness stations and shaded benches, then detour into charming cafés, craft breweries, and eclectic shops just off the trail.

Families will delight in playgrounds and open lawns at Ridgeway and Walsh Parks, where seasonal events like yoga meetups or outdoor movie nights bring communities together. With ADA-compliant ramps, bike racks, drinking fountains, and clear wayfinding at Ashland, Western, and Milwaukee access points, The 606 is effortless to navigate. The Trail is open daily from dawn until dusk and is free to all.

2. Explore Millennium Park and Cloud Gate

Millennium Park ranks among the most iconic Chicago things to do, offering a blend of art, architecture, and green spaces in the heart of the Loop. Wander through the serene Lurie Garden, where native prairie plants thrive alongside winding pathways. Marvel at Frank Gehry's stainless-steel bandshell at the Jay Pritzker Pavilion, which hosts free concerts and film screenings under the open sky. Pause beneath Anish Kapoor's reflective sculpture, Cloud Gate, affectionately known as "The Bean," to capture distorted skyline snapshots and interactive reflections.

Nearby Crown Fountain projects faces of Chicagoans through shimmering water walls, inviting cool respite in the summer months. The park's plazas and lawns frequently host seasonal events---from ice skating in winter at the McCormick Tribune Ice Rink to contemporary art installations on the BP Bridge. With wheelchair-accessible ramps, restrooms, and free Wi-Fi, Millennium Park ensures that you can enjoy this dynamic public realm.

3. Navy Pier and Continental Wheel

If you are seeking the best things to do in Chicago, Navy Pier delivers lakeside thrills, dining, and culture against a backdrop of Lake Michigan's sparkling expanse. Step aboard the 200-foot Centennial Wheel for panoramic views of the city skyline and azure waters, all from climate-controlled gondolas perfect year-round. The pier's family-friendly attractions include the Chicago Children's Museum, immersive 4D theaters, and the historic carousel. Savor Chicago deep-dish pizza or gourmet bites at waterfront eateries, then browse artisanal shops and seasonal pop-ups along the boardwalk. During summer evenings, gather for fireworks displays choreographed to live music, or join a twilight boat cruise for unique city vistas.

Accessible pathways, bike rentals, and convenient parking make Navy Pier effortless to navigate. Whether you seek romantic sunset rides, interactive exhibits, or lakeside festivals, Navy Pier stands out among Chicago things to do as an all-ages destination that captures the city's vibrant lakefront culture.

4. Architecture River Cruise

Embark on an architectural river cruise---one of the top things to do in Chicago---to unlock the history behind more than 50 landmark skyscrapers. Departing from the Chicago Riverwalk, expert guides aboard sleek vessels narrate tales of Fire-proof pioneers, Art Deco icons, and modern glass giants. Glide beneath ornate bridges as dusk lights cast shimmering reflections on the water, a photographer's dream. Learn how the Tribune Tower's neo-Gothic façade incorporates stones from global landmarks and why the John Hancock Center's X-bracing revolutionized structural engineering.

Ideal for families, couples, or solo travelers, these cruises offer complimentary headsets and accessible boarding for all guests. Seasonal specialty tours---like jazz-infused evening sails or holiday lights excursions---provide fresh perspectives on the skyline. This immersive journey ranks among the best things to do in Chicago, seamlessly blending education, entertainment, and unparalleled urban vistas in every river mile.

5. Immerse in Art Institute of Chicago

Visiting the Art Institute of Chicago remains a cornerstone of the best things to do in Chicago for art enthusiasts and casual visitors alike. Housed in a Beaux-Arts landmark, the museum's vast collections span from ancient artifacts to contemporary masterpieces. Stand before Grant Wood's "American Gothic," whose Americana charm has captivated audiences for decades, and linger by Georges Seurat's pointillist wonder, "A Sunday on La Grande Jatte." Explore immersive Impressionist galleries showcasing Monet's water lilies and Renoir's vibrant portraits amid serene natural light.

The modern wing features iconic works by Picasso, Pollock, and Warhol, while rotating special exhibitions spotlight emerging global talents. Visitor amenities include accessible entrances, coat checks, a café with skyline views, and multilingual audio guides. Located steps from Millennium Park, the Art Institute offers a cultural odyssey that solidifies its status among Chicago things to do, inviting you to explore art history's defining moments.

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Wrapping it up

Chicago dazzles with an unparalleled mix of urban adventures, cultural landmarks, and lakeside delights. From elevated strolls along The 606 and iconic selfies at Cloud Gate to panoramic skyline views aboard the Centennial Wheel and enlightening architectural river cruises, the city offers experiences for every taste. Art lovers will find endless inspiration at the Art Institute's world-class collections, while Millennium Park's seasonal events and Navy Pier's family-friendly attractions ensure nonstop entertainment. So, what are you waiting for? Book your flights to Chicago with Experian Airfare now and enjoy the vibrant city.