Chicago 6 Day Itinerary

Chicago 6-Day Itinerary

Day 1: Arrival and Exploring the Loop

  • Morning: Arrive in Chicago and check-in to your hotel. Recommended hotels:
    • The Langham Chicago (luxury)
    • Kimpton Hotel Monaco Chicago (boutique)
    • Freehand Chicago (hostel)
  • Afternoon:
    • Visit Millennium Park () and take a stroll through the beautiful Lurie Garden.
    • Explore the nearby Art Institute of Chicago (), one of the top art museums in the country.
  • Evening:
    • Head to The Berghoff () for dinner, a historic German restaurant serving classic dishes like sausages and schnitzel.
    • Take a sunset stroll along the Lake Michigan shoreline and enjoy the city skyline.

Day 2: Willis Tower and West Loop

  • Morning:
    • Start the day with breakfast at Au Cheval (), known for its trendy atmosphere and delicious diner fare.
    • Visit the Willis Tower (formerly Sears Tower) () for panoramic views of the city from the Skydeck on the 103rd floor.
  • Afternoon:
    • Explore the West Loop neighborhood, known for its vibrant street art, independent shops, and trendy restaurants.
    • Visit the United Center (), home of the Chicago Bulls and Blackhawks, for a guided tour.
  • Evening:
    • Enjoy dinner at Girl & the Goat (), a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
    • Catch a show or concert at the iconic Buddy Guy’s Legends () blues club.

Day 3: Lincoln Park and Zoo

  • Morning:
    • Visit the Lincoln Park Zoo (), a free zoo in the heart of the city, home to over 1,100 animals from around the world.
    • Take a stroll through the beautiful Lincoln Park Conservatory () and its stunning gardens.
  • Afternoon:
    • Explore the charming North Avenue Beach () and enjoy the lake views.
    • Visit the Peggy Notebaert Nature Museum (), featuring interactive exhibits on nature and the environment.
  • Evening:
    • Dine at Alinea (), a Michelin three-star restaurant known for its avant-garde, experimental cuisine.
    • Take a romantic evening stroll through the Lincoln Park neighborhood.

Day 4: Navy Pier and Lake Michigan

  • Morning:
    • Start the day with breakfast at Lou Mitchell’s (), a beloved institution serving up classic American fare.
    • Visit Navy Pier (), a lakefront attraction offering boat cruises, an amusement park, and entertainment options.
  • Afternoon:
    • Take a scenic Architectural River Cruise () to learn about Chicago’s rich architectural history.
    • Visit the Museum of Contemporary Art (), featuring innovative exhibitions and installations.
  • Evening:
    • Enjoy dinner at The Purple Pig (), offering creative small plates and craft cocktails.
    • Catch a fireworks display at Navy Pier (seasonal).

Day 5: Wicker Park and Bucktown

  • Morning:
    • Explore the trendy Wicker Park neighborhood, known for its vintage shops, record stores, and street art.
    • Visit the Wicker Park Farmers Market () for fresh produce and artisanal goods.
  • Afternoon:
    • Take a stroll through the charming Bucktown neighborhood, featuring boutiques, galleries, and restaurants.
    • Visit the iconic Double Door (), a music venue hosting local and national acts.
  • Evening:
    • Dine at Big Star (), a retro-style taco joint with outdoor seating and margaritas.
    • Enjoy live music or comedy at the legendary Second City ().

Day 6: Hyde Park and Museum of Science and Industry

  • Morning:
    • Visit the University of Chicago campus, featuring beautiful Gothic Revival architecture.
    • Explore the Museum of Science and Industry (), showcasing interactive exhibits on science and technology.
  • Afternoon:
    • Take a stroll through the picturesque Hyde Park neighborhood, featuring beautiful parks and gardens.
    • Visit the DuSable Museum of African American History (), dedicated to preserving African American culture and history.
  • Evening:
    • Enjoy dinner at The Promontory (), offering farm-to-table cuisine with stunning views of Lake Michigan.
    • Catch a show or concert at the Hyde Park neighborhood’s various music venues.

Transportation

  • Getting Around: Chicago has a comprehensive public transportation system, including buses and trains (the ‘L’). You can use the Ventra app to pay for fares.
  • Ride-hailing: Uber and Lyft operate in Chicago, but be aware of surge pricing during peak hours.

Tips and Essentials

  • Weather: Pack layers for unpredictable Midwestern weather. Summer can be hot and humid, while winters are cold and snowy.
  • Safety: Be mindful of your surroundings, especially at night. Avoid walking alone in dimly lit areas.
  • Tipping: 15% to 20% is standard for good service at restaurants and bars.
  • Chicago-style Pizza: Try Lou Malnati’s () or Pequod’s Pizza () for a classic deep-dish experience.

Other Interests

  • Sports: Catch a Cubs game at Wrigley Field (), a White Sox game at Guaranteed Rate Field (), or a Bears game at Soldier Field ().
  • Music: Explore the city’s vibrant music scene, from blues and jazz to rock and electronic.
  • Food Tours: Take a guided tour to sample Chicago’s diverse culinary offerings, from deep-dish pizza to craft beer.

Enjoy your trip to Chicago!