5 day itinerary for Chicago

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Here's an ideal itinerary for 5 days in Chicago:

Day 1:

  • Start your day with a visit to Millennium Park, where you can see the famous Cloud Gate sculpture (also known as "The Bean") and take a stroll through the Lurie Garden.
  • Next, head over to the Art Institute of Chicago, one of the oldest and largest art museums in the country. Spend a few hours exploring the galleries and admiring works by artists like Monet, Van Gogh, and Picasso.
  • For lunch, grab a deep-dish pizza at Lou Malnati's or Giordano's, two of the city's most famous pizzerias.
  • In the afternoon, take a riverboat architecture tour to learn about the history and design of Chicago's iconic buildings.
  • End your day with a visit to Navy Pier, where you can ride the Ferris wheel, play mini-golf, and enjoy views of Lake Michigan.

Day 2:

  • Start your day with a visit to the Museum of Science and Industry, which has interactive exhibits on everything from space travel to genetics.
  • For lunch, head to Portillo's for a classic Chicago-style hot dog or Italian beef sandwich.
  • In the afternoon, explore the neighborhoods of Wicker Park and Bucktown, which are known for their trendy shops, restaurants, and street art.
  • End your day with a comedy show at Second City, the famous improv theater that launched the careers of comedians like Tina Fey and Steve Carell.

Day 3:

Day 4:

  • Start your day with a visit to the Lincoln Park Zoo, which is free and open year-round. See animals like lions, tigers, and bears (oh my!).
  • For lunch, head to the nearby Lincoln Park neighborhood, which has plenty of restaurants and shops to explore.
  • In the afternoon, take a bike ride along the 606 Trail, a former elevated railway that's been converted into a park and trail system.
  • End your day with a visit to the Chicago Theatre, a historic venue that hosts concerts, plays, and other performances.

Day 5:

  • Start your day with a visit to the Willis Tower (formerly known as the Sears Tower), which has an observation deck on the 103rd floor with panoramic views of the city.
  • For lunch, head to Chinatown, where you can try dim sum or other Chinese specialties.
  • In the afternoon, take a stroll through the Magnificent Mile, a shopping district that's home to high-end stores like Neiman Marcus and Saks Fifth Avenue.
  • End your day with a sunset cruise on Lake Michigan, where you can enjoy views of the city skyline and watch the sun dip below the horizon.

I hope this itinerary gives you some ideas for your trip to Chicago!

Places of interest

Millennium Park Chicago

Millennium Park

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Art Institute of Chicago Chicago

Art Institute of Chicago

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Lou Malnati's Chicago

Lou Malnati's

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Giordano's Chicago


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Riverboat architecture tour Chicago

Riverboat architecture tour

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Navy Pier Chicago

Navy Pier

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Museum of Science and Industry Chicago

Museum of Science and Industry

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Portillo's Chicago


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Wicker Park Chicago

Wicker Park

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Bucktown Chicago


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Second City Chicago

Second City

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Field Museum Chicago

Field Museum

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West Loop neighborhood Chicago

West Loop neighborhood

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Girl & the Goat Chicago

Girl & the Goat

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Au Cheval Chicago

Au Cheval

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Publican Quality Meats Chicago

Publican Quality Meats

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Lakefront Trail Chicago

Lakefront Trail

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Adler Planetarium Chicago

Adler Planetarium

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Lincoln Park Zoo Chicago

Lincoln Park Zoo

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Lincoln Park neighborhood Chicago

Lincoln Park neighborhood

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606 Trail Chicago

606 Trail

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Chicago Theatre Chicago

Chicago Theatre

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Willis Tower Chicago

Willis Tower

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Chinatown Chicago


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Magnificent Mile Chicago

Magnificent Mile

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Sunset cruise on Lake Michigan Chicago

Sunset cruise on Lake Michigan

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