Chicago 2 Day Itinerary

Chicago in Two Days: A whirlwind Tour

This itinerary packs the highlights of Chicago into a quick but memorable trip.

Where to Stay:

  • Budget: Freehand Chicago (hostel with private rooms), The Willows Hotel
  • Mid-Range: The Hoxton, Thompson Hotel
  • Luxury: The Peninsula Chicago, Four Seasons Hotel Chicago

Transportation:

  • CTA “L” Train: Efficient and affordable way to get around the city. Purchase a Ventra card for easy access.
  • Divvy Bikes: Bike sharing program with stations throughout the city.
  • Taxi/Ride-Sharing: Uber and Lyft are readily available.

Things to Know:

  • Chicago weather can be unpredictable, so pack layers!
  • Tipping is customary in restaurants and bars (15-20%).
  • Deep dish pizza is a must-try!

Day 1: Downtown Delights & Architectural Wonders

  • Morning:

    • Start your day with breakfast at Lou Mitchell’s (classic diner) or Wildberry Pancakes & Cafe (delicious pancakes).
    • Take an architectural boat tour along the Chicago River. This is a fantastic way to see the city’s iconic skyline and learn about its history.
    • Visit Millennium Park, home to Cloud Gate (“The Bean”), Crown Fountain, and Lurie Garden.

  • Afternoon:

    • Explore the Art Institute of Chicago, world-renowned for its Impressionist and Post-Impressionist collections.
    • Climb Willis Tower (formerly Sears Tower) for stunning panoramic views.

  • Evening:

    • Enjoy a delicious deep dish pizza at Lou Malnati’s Pizzeria or Giordano’s.
    • Catch a Broadway show in the Theatre District.

Day 2: Culture, History & Neighborhood Vibes

  • Morning:

    • Visit Navy Pier, a lively waterfront destination with rides, restaurants, and shops.
    • Take a stroll through Lincoln Park Zoo, one of the oldest zoos in the country (free admission!).
    • Explore the vibrant Wicker Park neighborhood, known for its independent boutiques, art galleries, and trendy cafes.

  • Afternoon:

    • Immerse yourself in history at the Field Museum of Natural History or the Museum of Science and Industry.
    • Head to the Magnificent Mile for upscale shopping and dining.

  • Evening:

    • Enjoy a delicious meal in the West Loop neighborhood, known for its trendy restaurants and bars.
    • Catch live music at one of Chicago’s many blues clubs.

Other Things to Consider:

  • Chicago Cubs Game: If you’re visiting during baseball season, catching a game at Wrigley Field is an unforgettable experience.
  • Riverwalk: Take a leisurely walk along the scenic Chicago Riverwalk for beautiful city views.
  • Second City Improv: Experience world-class improvisational comedy at this legendary venue.

Tips:

  • Buy a CityPASS for discounted admission to top attractions.
  • Plan your itinerary in advance, as popular attractions can get crowded.
  • Wear comfortable shoes, as you’ll be doing a lot of walking!