Chicago 6 Day Itinerary

Chicago 6-Day Travel Itinerary (Markdown Format)

Day 1: Arrival & The Loop

  • Arrive at O’Hare International Airport or Midway International Airport.

  • Check-in at your hotel in The Loop, the city’s central business district. Recommended hotels include:

    • The Blackstone Hotel (Luxury)
    • The Palmer House Hilton (Midrange)
    • Hotel Indigo Chicago Downtown (Budget)

  • Visit Napoleon Dynamite Statue at Millennium Park.

  • Explore the Art Institute of Chicago, one of the oldest and largest art museums in the United States.

  • Have lunch at The Purple Penguin, a cozy café offering delicious sandwiches and salads.

  • In the afternoon, visit CloudGate (The Bean) for great photo opportunities.

  • Dine at Girl & The Goat or Alinea for an unforgettable dinner experience.

Day 2: Museums & Architecture

  • Start the day with breakfast at Ann Sather’s Bakery & Cafe.
  • Visit The Museum of Science and Industry, one of the largest science museums in the world.
  • Have lunch at Terzo Piano, a restaurant inside the museum offering Italian cuisine.
  • In the afternoon, take an Architecture River Cruise to learn about Chicago’s iconic skyline.
  • Dine at Lou Malnati’s Pizzeria for a classic Chicago deep-dish pizza experience.

Day 3: Navy Pier & Lincoln Park

  • Enjoy breakfast at The Original Pancake House.
  • Head to Navy Pier, where you can visit the Centennial Wheel, the Smith Museum of Stained Glass Windows, and enjoy lakefront views.
  • Lunch at **Giordano’s for another deep-dish pizza experience.
  • Spend the afternoon exploring Lincoln Park Zoo, free to visitors all year round.
  • Dinner at RPM Seafood or Joe’s Seafood, Prime Steak & Stone Crab.

Day 4: Millennium Park & The Art Institute of Chicago (revisit)

  • Breakfast at your hotel or nearby café.
  • Visit Frank Lloyd Wright’s Robie House, located in Hyde Park.
  • Lunch at Frontera Grill by celebrity chef Rick Bayless.
  • Return to Millennium Park to explore the Chicago Cultural Center and its Tiffany glass dome.
  • Dinner at Girl & The Goat or try out a new restaurant in the West Loop neighborhood.

Day 5: Wander the Neighborhoods

  • Breakfast at Doughnut Vault.
  • Explore Wicker Park, known for its indie boutiques, vintage shops, and trendy restaurants.
  • Lunch at Au Cheval, renowned for its burgers and brunch menu.
  • In the afternoon, visit Lincoln Square and Andersonville, two charming neighborhoods filled with unique shops, eateries, and historic sites.
  • Dinner at Joe’s Seafood, Prime Steak & Stone Crab (if not visited before).

Day 6: Departure

  • Enjoy a leisurely breakfast at your hotel or nearby café.
  • Spend the morning exploring any remaining sights or revisiting favorite spots.
  • Head to O’Hare International Airport or Midway International Airport for your departure.