Chicago, famously known as the Windy City, is a vibrant metropolis offering an eclectic mix of art, culture, entertainment, and outdoor adventure. Whether you’re a first-time visitor or a seasoned traveler, the city’s attractions will leave you spellbound.
From architectural wonders to buzzing neighborhoods, Chicago offers a dynamic range of experiences for every type of traveler. Here’s a guide to some of the most fun things to do in Chicago, guaranteed to make your trip unforgettable.
Explore Millennium Park and “The Bean”
No visit to Chicago is complete without stopping at Millennium Park. This urban oasis is home to the iconic Cloud Gate sculpture, affectionately called “The Bean.” Its reflective surface creates mesmerizing photo opportunities, making it one of the city’s most Instagrammable spots.
Stroll through the park’s lush gardens, marvel at the Crown Fountain’s interactive water display, or attend one of the many free concerts and events hosted at the Jay Pritzker Pavilion. In the winter, the park transforms into a winter wonderland with ice skating beneath the city skyline.
Take an Architectural River Cruise
Chicago’s skyline is a masterpiece of architectural innovation, and the best way to appreciate it is from the water. An architectural river cruise offers a fascinating perspective on the city’s storied buildings, designed by legends like Frank Lloyd Wright and Mies van der Rohe.
These narrated cruises provide rich insights into the history and design of landmarks such as the Willis Tower, Tribune Tower, and Marina City. It’s both an educational and visually stunning experience that you won’t want to miss.
Wander Around Navy Pier
Navy Pier is a hub of entertainment for all ages. Stretching along Lake Michigan, this iconic destination is packed with attractions, including the Centennial Wheel, which offers breathtaking views of the city and lake.
Enjoy live performances, shop for unique souvenirs, or savor delicious food at waterfront restaurants. If you’re visiting in the summer, catch a fireworks display lighting up the night sky. Navy Pier is also a launching point for boat tours, including speedboats and dinner cruises.
Immerse Yourself in Art at the Art Institute of Chicago
Art lovers will find paradise at the Art Institute of Chicago. Renowned for its extensive collection of masterpieces, the museum houses works by Van Gogh, Monet, and Seurat, among others.
The modern wing, designed by architect Renzo Piano, features cutting-edge contemporary art exhibits. Even if you’re not a die-hard art enthusiast, the museum’s grandeur and iconic lions at the entrance make it a must-visit.
Savor Chicago’s Culinary Scene
One of the most fun things to do in Chicago is indulging in its world-famous food. Start with a slice of deep-dish pizza from legendary spots like Lou Malnati’s or Giordano’s. For something lighter, try a Chicago-style hot dog loaded with mustard, onions, relish, and pickles (but hold the ketchup!).
The city’s dining scene extends far beyond its iconic dishes. Explore Michelin-starred restaurants and ethnic eateries in neighborhoods like Pilsen and Chinatown, or grab a bite at one of the many food halls, such as Time Out Market.
Visit the Field Museum and Shedd Aquarium
For an educational yet entertaining experience, head to the Museum Campus, home to the Field Museum and Shedd Aquarium. At the Field Museum, you can meet “Sue,” the largest and most complete T. rex fossil ever discovered.
Next door, the Shedd Aquarium dazzles visitors with its marine life exhibits, including beluga whales, penguins, and coral reefs. Together, these attractions make for a fun and family-friendly day out.
Stroll Along the Chicago Riverwalk
The Chicago Riverwalk is a picturesque pathway along the river, offering stunning views of the city’s skyline. This pedestrian-friendly area features public art installations, cafes, and waterfront seating.
You can rent a kayak, grab a drink at one of the lively riverside bars, or simply enjoy a peaceful stroll. During the warmer months, the Riverwalk buzzes with activities, including live music and outdoor markets.
Catch a Game at Wrigley Field
Sports fans will love the electric atmosphere of Wrigley Field, home of the Chicago Cubs. Built-in 1914, this historic ballpark is a quintessential Chicago experience.
Even if you’re not a baseball fan, the energy of the crowd and the charm of Wrigleyville’s bars and restaurants make it a fun outing. If you visit during the off-season, consider taking a tour of the stadium to learn about its rich history.
Marvel at Views from the Skydeck or 360 Chicago
For breathtaking views of the city, visit the Skydeck at Willis Tower or 360 Chicago at the John Hancock Center. The Skydeck’s glass-floored “Ledge” allows visitors to step out above the city for a heart-pounding experience, while 360 Chicago features “Tilt,” a thrilling attraction that tilts visitors outward over the edge of the building.
Both observation decks provide stunning panoramic views of the city and Lake Michigan, making them ideal for capturing unforgettable photos.
Stay at Arlo Chicago for the Ultimate City Experience
When exploring all the fun things to do in Chicago, staying at Arlo Chicago puts you right in the heart of the action. Located steps from Millennium Park and the Chicago Riverwalk, this stylish hotel offers modern comforts and easy access to the city’s top attractions. Make Arlo Chicago your home base for an unforgettable Windy City adventure!
