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Chicago

5 day itinerary for Chicago

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Itinerary

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

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.

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.

Lou Malnati's Chicago

Lou Malnati's

Lou Malnati's is a famous Chicago-style deep dish pizza restaurant that has been serving up delicious pies since 1971. Their signature buttery crust, tangy tomato sauce, and gooey cheese make for a mouthwatering experience.

Giordano's Chicago

Giordano's

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

Riverboat architecture tour Chicago

Riverboat architecture tour

Enjoy a 90-minute architecture tour on the Chicago River and learn about the city's iconic buildings and their history.

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.

Museum of Science and Industry Chicago

Museum of Science and Industry

The Museum of Science and Industry in Chicago is one of the largest science museums in the world, featuring interactive exhibits and hands-on experiences for visitors of all ages.

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.

Wicker Park Chicago

Wicker Park

Wicker Park is a trendy neighborhood in Chicago known for its vibrant nightlife, street art, and boutique shopping.

Bucktown Chicago

Bucktown

Bucktown is a trendy neighborhood located on the northwest side of Chicago. It is known for its vibrant arts scene, unique boutiques, and diverse dining options.

Second City Chicago

Second City

Second City Chicago is a renowned comedy club and theater that has been entertaining audiences for over 60 years with its improv and sketch comedy shows.

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.

West Loop neighborhood Chicago

West Loop neighborhood

West Loop is a trendy neighborhood in Chicago known for its vibrant dining scene, art galleries, and boutique shops. It's also home to the United Center, where the Chicago Bulls and Blackhawks play.

Girl & the Goat Chicago

Girl & the Goat

Girl & the Goat is a trendy restaurant in Chicago that serves creative small plates with global flavors, using locally sourced ingredients.

Au Cheval Chicago

Au Cheval

Au Cheval is a popular restaurant in Chicago known for its delicious burgers and upscale diner atmosphere.

Publican Quality Meats Chicago

Publican Quality Meats

Publican Quality Meats is a butcher shop and cafe in Chicago that offers high-quality meats, sandwiches, and other deli items.

Lakefront Trail Chicago

Lakefront Trail

The Lakefront Trail in Chicago is an 18-mile long path that runs along the shore of Lake Michigan, offering stunning views of the city skyline and the lake. It is a popular spot for walking, running, biking, and rollerblading.

Adler Planetarium Chicago

Adler Planetarium

Adler Planetarium is a public museum dedicated to the study of astronomy and astrophysics. It features interactive exhibits, planetarium shows, and telescopes for visitors to explore the wonders of the universe.

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.

Lincoln Park neighborhood Chicago

Lincoln Park neighborhood

Lincoln Park is a vibrant neighborhood located on the North Side of Chicago. It is known for its beautiful parks, historic architecture, and lively entertainment scene.

606 Trail Chicago

606 Trail

The 606 Trail is a 2.7-mile elevated trail in Chicago that was once a railway line. It is now a popular destination for walkers, runners, and cyclists.

Chicago Theatre Chicago

Chicago Theatre

The Chicago Theatre is a historic landmark and entertainment venue located in the heart of downtown Chicago. It has hosted countless concerts, comedy shows, and theatrical performances since its opening in 1921.

Willis Tower Chicago

Willis 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. The tower offers stunning views of the city from its observation deck on the 103rd floor.

Chinatown Chicago

Chinatown

Chinatown Chicago is a vibrant neighborhood located on the South Side of Chicago, known for its rich history, delicious food, and unique cultural experiences.

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.

Sunset cruise on Lake Michigan Chicago

Sunset cruise on Lake Michigan

Enjoy a breathtaking sunset over Lake Michigan on this relaxing cruise. Take in the stunning views of Chicago's skyline while sipping on a cocktail and listening to live music.

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