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Chicago

3 day itinerary for Chicago

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Itinerary

Here's an ideal itinerary for 3 days in Chicago:

Day 1:

Start your day with a visit to the iconic Willis Tower, formerly known as the Sears Tower. Take the elevator up to the Skydeck on the 103rd floor for breathtaking views of the city. After that, head over to Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean." You can take some great photos here and enjoy the beautiful park surroundings.

For lunch, head to Lou Malnati's Pizzeria for some delicious deep-dish pizza. After lunch, take a stroll down Michigan Avenue, also known as the Magnificent Mile, for some shopping and sightseeing. End your day with a visit to Navy Pier, where you can ride the Ferris wheel and enjoy the stunning views of Lake Michigan.

Day 2:

Start your day with a visit to the Art Institute of Chicago, one of the oldest and largest art museums in the country. Spend a few hours exploring the museum's vast collection of art from around the world.

For lunch, head to Portillo's for some classic Chicago-style hot dogs and Italian beef sandwiches. After lunch, take a walk through Lincoln Park Zoo, which is free to enter and home to a variety of animals.

In the evening, catch a show at the famous Second City comedy club, where many famous comedians got their start. End your night with a drink at one of the many rooftop bars in the city, such as Cindy's or The J. Parker.

Day 3:

Start your day with a visit to the Field Museum, where you can learn about natural history and see Sue, the largest and most complete T-Rex skeleton ever discovered.

For lunch, head to Giordano's for some more delicious deep-dish pizza. After lunch, take a boat tour along the Chicago River to see the city's impressive architecture from a different perspective.

In the evening, head to Wrigleyville to catch a Cubs game at historic Wrigley Field. If there's no game, you can still explore the neighborhood and grab a drink at one of the many bars and restaurants in the area.

There you have it! Three days in Chicago filled with iconic landmarks, delicious food, and plenty of fun activities.

Places of interest

Willis Tower (formerly known as Sears Tower) Chicago

Willis Tower (formerly known as Sears Tower)

Willis Tower, formerly known as Sears Tower, is a 110-story skyscraper located in Chicago, Illinois. It was completed in 1973 and held the title of tallest building in the world until 1998.

Skydeck on the 103rd floor Chicago

Skydeck on the 103rd floor

Skydeck is an observation deck located on the 103rd floor of Willis Tower in Chicago, offering breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending four feet outside the building.

Millennium Park Chicago

Millennium Park

Millennium Park is a public park located in the heart of downtown Chicago. It features iconic landmarks such as the Cloud Gate sculpture (also known as "The Bean"), the Jay Pritzker Pavilion, and the Crown Fountain.

Cloud Gate sculpture (The Bean) Chicago

Cloud Gate sculpture (The Bean)

Cloud Gate, also known as "The Bean," is a public sculpture located in Millennium Park in Chicago. Designed by artist Anish Kapoor, the sculpture is made of stainless steel and reflects the city's skyline and surrounding environment.

Lou Malnati's Pizzeria Chicago

Lou Malnati's Pizzeria

Lou Malnati's Pizzeria is a Chicago-based restaurant chain known for its deep-dish pizza and Italian-American cuisine.

Michigan Avenue (Magnificent Mile) Chicago

Michigan Avenue (Magnificent Mile)

Michigan Avenue, also known as the Magnificent Mile, is a bustling commercial district in downtown Chicago. It is home to high-end shops, restaurants, and hotels, as well as iconic landmarks such as the John Hancock Center and the Wrigley Building.

Navy Pier Chicago

Navy Pier

Navy Pier is a popular tourist destination in Chicago, located on the shores of Lake Michigan. It offers a variety of attractions including rides, restaurants, shops, and entertainment.

Ferris wheel Chicago

Ferris wheel

The Ferris wheel in Chicago is an iconic landmark located at Navy Pier. It offers stunning views of the city skyline and Lake Michigan.

Art Institute of Chicago Chicago

Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States, featuring a vast collection of artworks from around the world.

Portillo's Chicago

Portillo's

Portillo's is a popular Chicago-based restaurant chain known for its hot dogs, Italian beef sandwiches, and chocolate cake shakes.

Lincoln Park Zoo Chicago

Lincoln Park Zoo

Lincoln Park Zoo is a free 35-acre zoo located in Chicago, Illinois. It is home to over 1,000 animals from around the world and offers a variety of exhibits and attractions for visitors of all ages.

Second City comedy club Chicago

Second City comedy club

Second City is a world-renowned comedy club in Chicago that has launched the careers of many famous comedians. It offers hilarious improv and sketch comedy shows that are sure to leave you laughing.

Rooftop bars (Cindy's or The J. Parker) Chicago

Rooftop bars (Cindy's or The J. Parker)

Cindy's is a rooftop bar located on the 13th floor of the Chicago Athletic Association Hotel. It offers stunning views of Millennium Park and Lake Michigan, along with creative cocktails and American cuisine.

Field Museum Chicago

Field Museum

The Field Museum is a natural history museum in Chicago, Illinois. It is one of the largest and most impressive museums in the world, with over 40 million specimens and artifacts on display.

Sue (largest and most complete T-Rex skeleton ever discovered) Chicago

Sue (largest and most complete T-Rex skeleton ever discovered)

Sue is the largest and most complete T-Rex skeleton ever discovered, on display at the Field Museum in Chicago.

Giordano's Chicago

Giordano's

Giordano's Chicago is a famous pizzeria known for its deep-dish pizza and other Italian-American dishes.

Boat tour along the Chicago River Chicago

Boat tour along the Chicago River

Enjoy a scenic boat tour along the Chicago River and take in the stunning architecture of the city's skyline. Learn about the history and culture of Chicago from knowledgeable guides on board.

Wrigleyville Chicago

Wrigleyville

Wrigleyville is a lively neighborhood located on the north side of Chicago, known for its iconic Wrigley Field stadium and vibrant nightlife scene.

Wrigley Field Chicago

Wrigley Field

Wrigley Field is a historic baseball stadium located in the heart of Chicago's North Side. It is home to the Chicago Cubs and has been a beloved landmark since it opened in 1914.

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