3 day itinerary for Chicago

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Here's an ideal itinerary for 3 days in Chicago, with a focus on shopping and food:

Day 1:

  • Start your day with breakfast at Wildberry Pancakes and Cafe, known for their delicious pancakes and omelets.
  • Head to the Magnificent Mile, one of the most famous shopping districts in the world. You'll find everything from high-end designer stores to popular chain retailers.
  • For lunch, stop by Eataly, a massive Italian marketplace that offers a variety of dining options, including pizza, pasta, and gelato.
  • After lunch, continue exploring the Magnificent Mile and make sure to check out Water Tower Place, a shopping mall with over 100 stores.
  • In the evening, head to Navy Pier, a popular tourist destination with restaurants, shops, and attractions like the Ferris wheel.

Day 2:

  • Start your day with breakfast at Lou Mitchell's, a classic diner that's been around since 1923.
  • Take a stroll through Millennium Park and see the famous Cloud Gate sculpture (also known as "The Bean").
  • For lunch, head to Portillo's, a Chicago institution known for their hot dogs and Italian beef sandwiches.
  • Spend the afternoon exploring the Wicker Park neighborhood, which has a variety of independent boutiques and vintage shops.
  • For dinner, try deep-dish pizza at Giordano's or Lou Malnati's, two of the most famous pizza places in Chicago.

Day 3:

Of course, there are many other great places to shop and eat in Chicago, but this itinerary should give you a good starting point for your trip!

Places of interest

Wildberry Pancakes and Cafe Chicago

Wildberry Pancakes and Cafe

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Magnificent Mile Chicago

Magnificent Mile

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Eataly Chicago


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Water Tower Place Chicago

Water Tower Place

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Navy Pier Chicago

Navy Pier

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Lou Mitchell's Chicago

Lou Mitchell's

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Millennium Park Chicago

Millennium Park

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Cloud Gate sculpture Chicago

Cloud Gate sculpture

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Portillo's Chicago


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Wicker Park neighborhood Chicago

Wicker Park neighborhood

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Giordano's Chicago


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Lou Malnati's Chicago

Lou Malnati's

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Yolk Chicago


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Art Institute of Chicago Chicago

Art Institute of Chicago

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Rick Bayless' Frontera Grill Chicago

Rick Bayless' Frontera Grill

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Lincoln Park neighborhood Chicago

Lincoln Park neighborhood

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Superdawg Drive-In Chicago

Superdawg Drive-In

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