Chicago, Illinois-4-day-itinerary

Day 1: Millennium Park and the Loop

  • Morning: Start your day with a visit to Millennium Park, one of Chicago’s most popular attractions. Take a stroll through the beautiful Lurie Garden, snap a photo in front of the famous “Cloud Gate” sculpture (aka “The Bean”), and catch some live music or street performers.
  • Lunch: Grab a bite to eat at Portillo’s, a Chicago institution serving up hot dogs, Italian beef sandwiches, and chocolate cake. Try their famous Hot Dog with relish, onions, tomatoes, sport peppers, and pickle slices!
  • Afternoon: Head over to the Willis Tower (formerly Sears Tower) for panoramic views of the city from 103 floors up. Take in the sights and sounds of Chicago’s bustling streets.
  • Dinner: For dinner, head to Girl & the Goat, a Mediterranean-inspired restaurant with creative small plates and wood-fired dishes.

Stay: Consider staying at the LondonHouse Chicago, a stylish boutique hotel in the Loop with comfortable rooms and great city views.

Transportation: Take the ‘L’ (elevated train) from Millennium Station to get around the city. Be sure to validate your Ventra card or purchase a day pass before boarding.

Tips: Don’t forget to bring sunscreen and layers for changing Chicago weather! Try to avoid traveling during rush hour if possible.

Day 2: The Art Institute of Chicago and Street Food

  • Morning: Spend the morning exploring The Art Institute of Chicago, one of the largest art museums in the country. Be sure to see famous works like “American Gothic” and “Nighthawks.”
  • Lunch: Grab some delicious street food at Pizzeria Uno or try a classic Chicago-style hot dog from Hot Doug’s, though be aware that Hot Doug’s has closed but you can still get their famous dogs at other locations around the city.
  • Afternoon: Visit the Tribune Tower, a stunning example of art deco architecture and former home of the Chicago Tribune newspaper.

Eat: For dinner, head to Au Cheval for some trendy diner food with creative burgers and sandwiches.

Stay: Consider staying at the Kimpton Hotel Allegro, a stylish boutique hotel in the Loop with comfortable rooms and great city views.

Transportation: Take the ‘L’ from Millennium Station to get around the city. Be sure to validate your Ventra card or purchase a day pass before boarding.

Things to know: Don’t miss out on trying some of Chicago’s famous street food, like hot dogs, Italian beef sandwiches, and deep-dish pizza!

Day 3: Navy Pier and Lake Michigan

  • Morning: Spend the morning exploring Navy Pier, a popular lakefront attraction with boat cruises, entertainment options, and beautiful views of Lake Michigan.
  • Lunch: Grab some lunch at Billy Goat Tavern, a Chicago institution famous for its cheeseburgers.
  • Afternoon: Visit the Chicago Shakespeare Theater or take a boat cruise of Lake Michigan.

Eat: For dinner, head to Blackbird, a modern American restaurant with creative dishes and great wine pairings.

Stay: Consider staying at the The Langham Chicago, a luxurious boutique hotel in the Gold Coast neighborhood with comfortable rooms and great city views.

Transportation: Take the ‘L’ from Navy Pier Station to get around the city. Be sure to validate your Ventra card or purchase a day pass before boarding.

Things to know: Don’t miss out on trying some of Chicago’s famous lakefront attractions, like Navy Pier and Lake Michigan!

Day 4: Wrigleyville and North Side

  • Morning: Spend the morning exploring Wrigleyville, a trendy neighborhood with great restaurants, bars, and shopping options.
  • Lunch: Grab some lunch at Portillo’s, a Chicago institution famous for its hot dogs and Italian beef sandwiches.
  • Afternoon: Visit the Lincoln Park Conservatory or take a stroll through Lincoln Park.

Eat: For dinner, head to The Purple Pig, a trendy restaurant with creative small plates and great cocktails.

Stay: Consider staying at the The Gwen, A Luxury Collection Hotel Chicago, a stylish boutique hotel in the Gold Coast neighborhood with comfortable rooms and great city views.

Transportation: Take the ‘L’ from Belmont Station to get around the city. Be sure to validate your Ventra card or purchase a day pass before boarding.

Things to know: Don’t miss out on trying some of Chicago’s famous Wrigleyville attractions, like the historic Wrigley Field stadium!

Note: The itinerary is just a suggestion and can be customized based on individual preferences and interests.