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Chicago

3 day itinerary for Chicago

Personalized with:

It's a business trip, so give ideas on what to do after work hours on Monday and tuesdays

I'll be downtown, provide ideas next only in downtown

Include the must try restaurants

Include best photography spots

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Itinerary

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

Day 1 (Monday):

  • After work hours, head to the Navy Pier. It's a great place to unwind and enjoy the beautiful views of Lake Michigan. You can take a ride on the Ferris wheel, visit the Chicago Children's Museum, or catch a show at the IMAX theater.
  • For dinner, try the famous deep-dish pizza at Giordano's. It's a Chicago staple and definitely worth trying.
  • For photography spots, head to the Skydeck at Willis Tower. You can get a stunning view of the city from the 103rd floor.

Day 2 (Tuesday):

  • After work hours, head to the Magnificent Mile. It's a shopper's paradise with high-end stores like Gucci, Louis Vuitton, and Burberry. You can also visit the John Hancock Center and take a ride to the 360 Chicago Observation Deck for a panoramic view of the city.
  • For dinner, try the Chicago-style hot dog at Portillo's. It's a classic and delicious.
  • For photography spots, head to Millennium Park. You can take a picture with the famous Cloud Gate sculpture, also known as "The Bean."

Day 3 (Wednesday):

  • After work hours, head to the Art Institute of Chicago. It's one of the oldest and largest art museums in the country, with a collection of over 300,000 works of art. You can also visit the nearby Grant Park and take a stroll through the beautiful gardens.
  • For dinner, try the Italian beef sandwich at Al's Beef. It's a local favorite and a must-try.
  • For photography spots, head to the Chicago Riverwalk. You can get a great view of the city skyline and take a boat tour to learn more about the city's architecture.

I hope this itinerary helps you make the most of your time in Chicago!

Places of interest

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.

Giordano's (restaurant) Chicago

Giordano's (restaurant)

Giordano's is a famous Chicago-style deep dish pizza restaurant that has been serving its signature pies since 1974.

Skydeck at Willis Tower Chicago

Skydeck at Willis Tower

Skydeck at Willis Tower Chicago is an observation deck located on the 103rd floor of the Willis Tower, offering breathtaking views of the city of Chicago.

Magnificent Mile Chicago

Magnificent Mile

Magnificent Mile is a prestigious shopping district in Chicago, known for its upscale stores, restaurants, and hotels. It stretches along Michigan Avenue from the Chicago River to Oak Street.

John Hancock Center Chicago

John Hancock Center

The John Hancock Center is a 100-story skyscraper located in Chicago, Illinois. It is one of the tallest buildings in the city and offers stunning views of Lake Michigan and the surrounding area.

360 Chicago Observation Deck Chicago

360 Chicago Observation Deck

360 Chicago Observation Deck is a popular tourist attraction located on the 94th floor of the John Hancock Center in downtown Chicago. Visitors can enjoy breathtaking views of the city skyline and Lake Michigan from the observation deck, which also features interactive exhibits and a thrilling TILT experience.

Portillo's (restaurant) Chicago

Portillo's (restaurant)

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

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.

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.

Grant Park Chicago

Grant Park

Grant Park is a large urban park in downtown Chicago, known for its iconic Buckingham Fountain and stunning views of Lake Michigan. It is home to many popular attractions, including the Art Institute of Chicago, Millennium Park, and the Museum Campus.

Al's Beef (restaurant) Chicago

Al's Beef (restaurant)

Al's Beef is a popular fast-food restaurant in Chicago known for its Italian beef sandwiches.

Chicago Riverwalk Chicago

Chicago Riverwalk

The Chicago Riverwalk is a scenic promenade along the Chicago River, featuring restaurants, bars, and outdoor activities.

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