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Chicago, also known as the “Windy City,” is located in the Midwest region of the United States and is known for its rich culture, delicious food, and iconic architecture.

With so much to see and do, it can be overwhelming to plan a trip to Chicago. Here are the top things to see and do while in the city.

Best Things To Do in Chicago

1. Enjoy the Views From Willis Tower

Standing at 1,450 feet tall, Willis Tower offers breathtaking views of the city from its Skydeck on the 103rd floor. 

Willis Tower Chicago

The Willis Tower Skydeck is a must-see destination for visitors. The Skydeck provides a spectacular view of the city, including the Willis Tower and the Chicago River. Visitors can also step out onto The Ledge, a series of glass boxes that extend out from the building, providing an incredible perspective of the city below.

The Skydeck also offers interactive exhibits and a history of the building’s construction.

2. Visit Millennium Park

Millennium Park is a must-see destination in Chicago. The park features a variety of iconic landmarks, including the famous “Cloud Gate” sculpture, also known as “The Bean.”

Downtown Chicago

This giant bean-shaped sculpture is made of polished stainless steel and reflects the city skyline and visitors. The park also features the Lurie Garden, an interactive Crown Fountain, and the Pritzker Pavilion, an outdoor concert venue.

3. Browse Art at the Art Institute of Chicago

The Art Institute of Chicago is one of the most prestigious art museums in the world. The museum features an extensive collection of art from around the globe, including works by Monet, Van Gogh, and Picasso. The museum also offers temporary exhibitions, lectures, and tours.

Art Institute Chicago

The institute’s collection is divided into two buildings, the main building, and the Modern Wing, which houses the museum’s contemporary art collection.

4. See a Game at Wrigley Field

Wrigley Field is a historic baseball stadium and home of the Chicago Cubs. The stadium offers tours of the facilities, including the press box, dugout, and the bleachers. Visitors can also catch a game during baseball season and enjoy the unique atmosphere of Wrigley Field.

Wrigley Field

5. Eat Deep Dish Pizza

You can’t visit Chicago without trying its most iconic dish: Deep Dish Pizza. Get the very best at the original restaurant where it was invented: Uno Pizzeria and Grill, or at their second restaurant Pizzeria Due. Lou Malnati’s also does an excellent deep-dish pizza.

Chicago Deep Dish Pizza

6. Stroll The Magnificent Mile

The Magnificent Mile is a stretch of Michigan Avenue that is home to some of the city’s best shopping, dining, and entertainment options. Visitors can find luxury brands, high-end department stores, and unique boutiques, as well as a variety of restaurants and bars.

The area also features the iconic Water Tower, one of the only buildings to survive the Great Chicago Fire of 1871.

7. Enjoy the Attractions of Navy Pier

Navy Pier is a popular lakefront attraction that offers a variety of activities, including boat tours, a Ferris wheel, and an IMAX theater. Visitors can also enjoy the Chicago Children’s Museum, the Smith Museum of Stained Glass Windows, and the Chicago Shakespeare Theater.

navy pier Chicago

The pier also offers a variety of dining and entertainment options, including a beer garden and a concert stage.

8. Do an Architecture River Cruise

Chicago is famous for its incredible architecture and rightfully so. The best way to experience and learn more about Chicago’s best architecture is by taking a river cruise with Chicago Architecture Foundation – it was rated as the number one boat tour in the U.S. by USA Today Readers! 

Chicago River

9. Visit The Museum of Science and Industry

The Museum of Science and Industry is one of the largest science museums in the world. The museum features interactive exhibits, live demonstrations, and a variety of hands-on experiences. Visitors can explore the museum’s permanent exhibits, including the Coal Mine, the U-505 submarine, and the Science Storms exhibit.

10. See A Show at The Chicago Theatre

The Chicago Theatre is a historic theater that hosts a variety of shows, including Broadway productions, concerts, and stand-up comedy. 

Chicago Theatre

Tips For Planning Your Trip To Chicago

To make the most of your time here, here are the main steps in organizing your trip to Chicago:

1. Determine the dates of your trip and the number of people traveling with you.

2. Research and book flights or transportation to Chicago.

3. Research and book accommodations, such as a hotel or vacation rental. Booking Ideal Charter will also make your traveling more comfortable and stress-free.

4. Plan out your itinerary and make reservations for any activities or attractions you want to visit, such as Willis Tower or the Art Institute of Chicago.

5. Research and make reservations at restaurants for meals.

6. Pack and plan for any necessary items, such as clothing and travel documents.

7. Make sure you have a valid passport if traveling internationally.

8. Confirm all reservations and travel plans before leaving for the trip.

Chicago at night

Chicago is a beautiful city that offers a wide variety of things to see and do. Whether you’re interested in art, architecture, or outdoor activities, there’s something for everyone here. With so many great options to choose from, you’re sure to have a fantastic time exploring all the city has to offer.

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