Chicago Usa 6 Day Itinerary

Chicago 6-Day Travel Itinerary

(Note: This itinerary is a suggestion for a leisurely visit and can be adjusted based on personal preferences.)

Day 1: Arrival & Exploring The Loop

  • Check-in at your hotel (e.g., Hotel Allegro, The Wit Hotel Chicago, or Palmer House Hilton) located in the Loop, Chicago’s downtown district.
  • Start with a visit to Navy Pier. Explore the Centennial Wheel, enjoy Lake Michigan views, and visit the Chicago Children’s Museum (if traveling with kids).
  • Lunch at Giordano’s for famous deep-dish pizza.
  • Afternoon visit to The Art Institute of Chicago showcasing a vast collection of American and European art, including American Galleries and Modern & Contemporary Art.
  • Evening stroll along Michigan Avenue and visit The Bean, Millennium Park’s iconic sculpture.
  • Dinner at Girl & The Goat, a James Beard Award-winning restaurant serving innovative small plates.

Day 2: Museum Campus & Millennium Park

  • Breakfast at Ella Elliott Café in the Loop.
  • Head to Museum Campus: visit The Field Museum, Shedd Aquarium, and Adler Planetarium.
  • Grab lunch at Pizano’s Pizza & Pasta, a Chicago institution.
  • Afternoon visit to Millennium Park for more exploring and relaxation, or attend a free concert at the Jay Pritzker Pavilion (check schedule).
  • Dinner at Alinea, one of the world’s top restaurants (reservations recommended well in advance). Alternatively, try Blackbird, another Michelin-starred restaurant.

Day 3: Lincoln Park & Wrigleyville

  • Breakfast at Ann Sather’s Café in Lincoln Park.
  • Visit Lincoln Park Zoo, one of the oldest zoos in North America, with free admission!
  • Lunch at The Purple Pig for Mediterranean small plates and exceptional wines.
  • Afternoon exploring Lincoln Park: walk along the lakefront, visit Lincoln Park Conservatory, or rent a bike to explore the park.
  • Dinner in Wrigleyville (home of Wrigley Field): try Harry Caray’s 7th Inning Stretch for classic Chicago cuisine and sports memorabilia.

Day 4: Architecture Tour & The Magnificent Mile

  • Breakfast at your hotel or Bistronomic, a French bistro in the Gold Coast neighborhood.
  • Morning architecture tour on Shoreline Sightseeing’s Chicago Architecture River Cruise.
  • Lunch at Lou Malnati’s Pizzeria for another famous Chicago deep-dish pizza experience.
  • Afternoon shopping along The Magnificent Mile for top brands and unique souvenirs.
  • Dinner at Girl & The Goat, if you missed it earlier in the week, or try Alinea’s more casual sister restaurant, Next Door.

Day 5: Navy Pier & River North

  • Breakfast at The Signature Room at the 95th for stunning views and a sophisticated meal.
  • Return to Navy Pier in the morning: visit the Chicago Shakespeare Theater or explore the Smith Museum of Stained Glass Windows.
  • Lunch at Girl & The Goat (if you haven’t already) or RPM Steak for contemporary American steakhouse fare.
  • Afternoon exploring River North: walk along the river, check out art galleries, and visit The Museum of Contemporary Art Chicago.
  • Dinner at Alinea, if you haven’t already tried it during this trip. Alternatively, try RPM Italian for modern Italian cuisine.

Day 6: Departure & Last Bites

  • Breakfast at your hotel or a local café.
  • Spend the morning exploring any neighborhoods missed during the week or revisit favorite spots before departing Chicago.
  • Lunch at Frontera Grill, Rick Bayless’ famous restaurant offering innovative Mexican cuisine.
  • Head to O’Hare International Airport for your departure flight.