Chicago, Illinois 6 Day Itinerary

Chicago, Illinois 6-Day Travel Itinerary (Markdown format)

Day 1: Arrival & The Loop

  • Check-in at your hotel in downtown Chicago (recommended: The Loews Chicago Hotel or The Langham, Chicago)
  • Start with a visit to the Willis Tower (formerly Sears Tower), where you can enjoy panoramic views of the city from Skydeck’s Ledge.
  • Explore Millennium Park, home to famous art installations such as the Cloud Gate (also known as “The Bean”).
  • Grab lunch at Alinea or Girl & The Goat, two renowned Chicago eateries.
  • In the afternoon, visit the Art Institute of Chicago and the nearby Magnificent Mile for shopping and sightseeing.
  • End your day with dinner at Lou Malnati’s Pizzeria for a taste of classic Chicago-style deep dish pizza.

Day 2: Museum Campus & Lakefront

  • Spend the morning at Museum Campus: visit the Field Museum, Shedd Aquarium, and Adler Planetarium.
  • For lunch, grab a bite from one of the food trucks often stationed on the campus or head to The Purple Pig.
  • Afternoon: Explore Navy Pier with its Ferris wheel, boat tours, and gardens. Visit the Chicago Children’s Museum if you’re traveling with kids.
  • Head to Lincoln Park Zoo in the late afternoon, a free-to-enter zoological garden with penguins, giraffes, and more.
  • Enjoy dinner at Au Cheval or Girl & The Goat, if you didn’t get a chance on day 1.

Day 3: Architecture Tour & Wrigley Field

  • Start the day with a guided Architecture River Cruise. Learn about Chicago’s iconic buildings from knowledgeable tour guides.
  • For lunch, try The Signature Room at The 95th, located in the John Hancock Center, offering fantastic views of the city.
  • In the afternoon, visit Wrigley Field, home of the Chicago Cubs, for a game or take a tour if there isn’t a match that day.
  • Head to Lincoln Square for dinner and explore this vibrant neighborhood with its unique shops and restaurants.

Day 4: Lincoln Park & Lakeview Neighborhoods

  • Morning visit to the Lincoln Park Conservatory, home to numerous tropical plants, palm trees, and seasonal exhibits.
  • Explore the nearby ZooLab, where you can get up close with reptiles, insects, and other exotic creatures.
  • Grab lunch at Hackney’s Café or J.P. Graziano Grocery, both in Lincoln Park.
  • Afternoon: Head to Wrigleyville (the area around Wrigley Field) for a taste of local bars and pubs, such as Murphy’s Bleachers or The Cubby Bear.
  • Have dinner at Little Goat Diner, a casual eatery by celebrity chef Graham Elliot.

Day 5: Hyde Park & University of Chicago

  • Spend the morning in Hyde Park, home to the University of Chicago. Visit the Frank Lloyd Wright-designed Robie House.
  • Take a stroll along the lakefront to Promontory Point, offering beautiful views and a peaceful atmosphere.
  • For lunch, try The Duck Inn or Akasha Restaurant.
  • Afternoon: Explore the Museum of Science and Industry, one of the largest science museums in the world.
  • End your day with dinner at Frontera Grill, a Mexican eatery by celebrity chef Rick Bayless.

Day 6: Departure & Last Bites

  • Have breakfast at Ann Sather’s or The Original Pancake House.
  • Spend your last hours shopping for souvenirs in the neighborhood around your hotel or taking a leisurely walk along the Riverwalk.
  • Depart from O’Hare International Airport (ORD) or Midway International Airport (MDW).

Things to Know:

  • Chicago is known for its cold and snowy winters, so be sure to pack accordingly if visiting between October and March.
  • The CTA (Chicago Transit Authority) provides an extensive public transportation system that includes buses and trains, making it easy to get around the city.
  • Tipping is customary in Chicago restaurants; budget about 20% of your bill for tips.
  • Don’t forget to sample local specialties like Chicago-style hot dogs, Italian beef sandwiches, and Malört, a unique liquor made from wormwood.
  • Check opening hours and ticket prices for attractions before visiting, as some may have different schedules on weekends or holidays.