Chicago, Illinois-6-day-itinerary

Chicago: 6-Day Itinerary

Where to Stay:

  • Budget: Hostelling International Chicago, Freehand Chicago
  • Mid-Range: The Robey, Hotel EMC2
  • Luxury: The Peninsula Chicago, Four Seasons Hotel Chicago

Transportation:

  • CTA “L” Train: Extensive network covering most attractions. Purchase a Ventra card for easy access.
  • Buses: Complement the “L” train system. Use Google Maps or the CTA app for routes and schedules.
  • Divvy Bikes: Bike-sharing program with stations throughout the city.
  • Walking: Many attractions are within walking distance, especially downtown.

Things to Know:

  • Chicago weather can be unpredictable; pack layers!
  • Tipping is customary (15-20%) for restaurant service and other services.
  • Purchase a CityPASS for discounted entry to popular attractions.

Day 1: Exploring the Loop & Magnificent Mile

  • Morning: Start with a stroll through Millennium Park, admiring Cloud Gate (“The Bean”) and Crown Fountain.
  • Afternoon: Head north to the Magnificent Mile, browsing luxury shops and iconic department stores like Macy’s.
  • Evening: Enjoy dinner at RPM Steak (upscale) or Lou Malnati’s Pizzeria (deep-dish pizza heaven).

Day 2: Art & Architecture

  • Morning: Visit the Art Institute of Chicago, home to masterpieces by Monet, Picasso, and Warhol.
  • Afternoon: Take a Chicago Architecture Foundation River Cruise for stunning views of the city’s skyline.
  • Evening: Catch a Broadway show at the historic Chicago Theatre.

Day 3: Museums & Neighborhood Vibes

  • Morning: Explore the Field Museum with its dinosaur skeletons, ancient Egyptian artifacts, and diverse exhibits.
  • Afternoon: Wander through Lincoln Park Zoo (free entry!), home to over 1,000 animals.
  • Evening: Indulge in a delicious meal in the trendy Lincoln Park neighborhood at Alinea (Michelin-starred) or Cafe Ba-Ba-Reeba! (Spanish tapas).

Day 4: Wrigleyville & Blues

  • Morning: Take a tour of Wrigley Field, the iconic home of the Chicago Cubs.
  • Afternoon: Explore the lively bars and restaurants in Wrigleyville.
  • Evening: Experience live blues music at Kingston Mines or Buddy Guy’s Legends.

Day 5: Garfield Park & Second City Comedy

  • Morning: Discover Garfield Park Conservatory, a stunning indoor botanical garden with diverse plant collections.
  • Afternoon: Relax and enjoy the sunshine in nearby Garfield Park.
  • Evening: Laugh your heart out at Second City, the legendary improv comedy club.

Day 6: Lakefront & Farewell

  • Morning: Stroll or bike along the scenic Lakefront Trail, enjoying views of Lake Michigan.
  • Afternoon: Relax on the beach at North Avenue Beach or visit Navy Pier for amusement rides and attractions.
  • Evening: Savor a final Chicago meal at RPM Italian (modern Italian) before heading to the airport.

Tips:

  • Consider purchasing a Chicago CityPASS for discounted entry to major attractions.
  • Explore different neighborhoods like Wicker Park, Andersonville, and Pilsen for unique experiences.
  • Don’t forget to try a Chicago hot dog (no ketchup!) and indulge in deep-dish pizza.

Enjoy your trip to the Windy City!