48 Hours in Chicago, USA: 10 Cool Things To Absolutely Do

Chicago, known as the “Windy City,” is a vibrant metropolis that offers a plethora of unforgettable experiences. Whether you’re a food enthusiast, architecture lover, or history buff, there is something for everyone in this dynamic city. If you find yourself with just 48 hours to explore Chicago, here are 10 cool things you absolutely must do.

1. Admire the Skyline from the Willis Tower Skydeck

One of the most iconic landmarks in Chicago, the Willis Tower (formerly known as the Sears Tower) offers breathtaking views of the city from its Skydeck. Step into the glass-floored balcony, known as The Ledge, which extends four feet outside the tower, allowing visitors to marvel at the stunning views from 1,353 feet above ground. This exhilarating experience is not for the faint of heart, but definitely worth it for the unforgettable panoramic vistas of Chicago’s beautiful skyline.

2. Explore Millennium Park and Cloud Gate

Located in downtown Chicago, Millennium Park is a vibrant urban oasis that showcases public art and stunning landscapes. At the heart of the park, you’ll find Cloud Gate, also known as “The Bean.” This iconic sculpture by artist Anish Kapoor is a must-see attraction. Its polished stainless-steel surface reflects the city’s skyline, offering unique photo opportunities. Take a leisurely stroll through the park, relax by the serene Lurie Garden, and enjoy the various live performances and events that often take place here.

3. Indulge in Deep Dish Pizza

No visit to Chicago is complete without trying their famous deep dish pizza. Sink your teeth into a slice of heaven with a thick, buttery crust, topped with gooey cheese, chunky tomato sauce, and your favorite toppings. Lou Malnati’s Pizzeria, Giordano’s, and Pequod’s Pizza are just a few of the renowned establishments where you can savor this iconic Chicago delicacy. The hearty and satisfying nature of deep dish pizza makes it the perfect comfort food, and a true taste of the city’s culinary scene.

4. Discover the Art Institute of Chicago

With its extensive collection spanning thousands of years, the Art Institute of Chicago is a treasure trove for art enthusiasts. From iconic masterpieces such as Grant Wood’s “American Gothic” to a vast collection of ancient Egyptian artifacts, this renowned museum offers something for art lovers of all ages. Don’t miss the opportunity to see famed Impressionist and Post-Impressionist paintings, including works by Monet, Renoir, and Van Gogh. The Art Institute of Chicago is a cultural gem that showcases the city’s rich artistic heritage.

5. Take an Architectural Boat Tour on the Chicago River

Known for its incredible architecture, Chicago is home to many notable buildings and skyscrapers. An architectural boat tour on the Chicago River is an excellent way to appreciate the city’s impressive skyline and learn about its architectural history. As you cruise along the water, knowledgeable guides provide fascinating insights into the iconic structures that populate the river’s edge, such as the Wrigley Building, the Tribune Tower, and the Marina City towers. This tour showcases the ingenuity and beauty of Chicago’s architectural marvels.

6. Experience Chicago’s Blues Scene

Chicago has a deep-rooted history in the blues genre, and experiencing the city’s vibrant blues scene is a must-do for music enthusiasts. Head to popular blues clubs such as Buddy Guy’s Legends or Kingston Mines, where you can enjoy live performances by talented musicians, both established and up-and-coming. Immerse yourself in the soulful tunes, energetic atmosphere, and the rich musical heritage that Chicago is known for. Whether you’re a devoted fan or simply appreciate good music, a night out in a blues club is an unforgettable experience.

7. Explore Navy Pier and Lake Michigan

To fully embrace Chicago’s maritime charm, visit Navy Pier, a lively entertainment destination on the shores of Lake Michigan. Take a leisurely stroll along the pier, enjoy the stunning views of the lake, and indulge in delicious treats from various food vendors. For a thrilling experience, hop on one of the amusement rides or embark on a scenic cruise. Navy Pier also hosts various cultural events, fireworks shows, and even a Ferris wheel, making it an ideal place to spend a sunny afternoon or evening.

8. Get Adventurous on the Chicago 606 Trail

For outdoor enthusiasts, a visit to the Chicago 606 Trail is a must. This elevated trail is built on an abandoned railway line, offering a unique perspective of the city as you bike, jog, or walk through several diverse neighborhoods. The 2.7-mile trail provides a scenic escape from the hustle and bustle of the streets below, with beautiful landscaping, public art installations, and the opportunity to experience Chicago’s vibrant communities firsthand. Soak in the urban charm while staying active and exploring parts of the city off the beaten path.

9. Marvel at the Shedd Aquarium

Give your trip a touch of marine magic by visiting the Shedd Aquarium, home to over 32,000 aquatic animals from around the world. Explore fascinating exhibits such as the Amazon Rising, a replica of the Amazon rainforest, or the Wild Reef, where you can come face-to-face with sharks and sea turtles. The aquarium also offers interactive experiences, including beluga whale encounters and a chance to touch stingrays. The Shedd Aquarium is a captivating attraction that allows visitors to learn about and appreciate the wonders of the aquatic world.

10. Shop and Dine in the Magnificent Mile

Chicago’s Magnificent Mile is a shopper’s paradise, featuring a mile-long stretch of high-end boutiques, department stores, and luxury retailers. From the latest fashion trends to unique specialty shops, this bustling district has something for every style and taste. Indulge in some retail therapy at iconic stores like Bloomingdale’s or Saks Fifth Avenue, and then recharge with a delicious meal at one of the many world-class restaurants in the area. The Magnificent Mile is a haven for fashionistas, foodies, and anyone looking to experience the city’s vibrant energy.

Chicago is a city that effortlessly blends culture, history, and modernity, providing a diverse range of experiences for every traveler. With its stunning skyline, delicious cuisine, rich artistic heritage, and vibrant neighborhoods, this cosmopolitan destination should be on every adventurer’s list. Make the most of your 48 hours in the Windy City by immersing yourself in its unique atmosphere and ticking off these 10 cool things to do. Chicago is waiting to show you why it’s truly a city like no other.

Willis Tower Skydeck: https://theskydeck.com/
Millennium Park: https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html
Lou Malnati’s Pizzeria: https://www.loumalnatis.com/
Art Institute of Chicago: https://www.artic.edu/
Chicago Architecture Foundation River Cruise: https://www.architecture.org/tours/detail/chicago-architecture-foundation-river-cruise-aboard-chicagos-first-lady-cruises/
Buddy Guy’s Legends: https://buddyguy.com/
Navy Pier: https://navypier.org/
The 606: https://www.the606.org/
Shedd Aquarium: https://www.sheddaquarium.org/
Magnificent Mile: https://www.themagnificentmile.com/