Chicago 2 Day Itinerary

Day 1: Exploring Downtown Chicago

Morning

  • Start at Millennium Park: Begin your day by visiting the famous “Cloud Gate” sculpture (also known as “The Bean”) and take some amazing photos.
  • Take a stroll along the Lakefront Trail: Walk north along the lake shore and enjoy the beautiful views of Lake Michigan.

Lunchtime

  • Eat at Portillo’s: Try their famous Chicago-style hot dogs or Italian beef sandwiches. Be prepared for a lively atmosphere!

Afternoon

  • Visit the Art Institute of Chicago: Spend a few hours exploring one of the largest art museums in the country.
  • Take an Architecture River Cruise: Learn about Chicago’s rich architectural history on a guided boat tour.

Evening

  • Dine at Girl & the Goat: Enjoy Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard.
  • Explore the West Loop neighborhood: Discover trendy bars, restaurants, and boutiques in this vibrant area.

Where to Stay

  • The Wit Hotel: A stylish boutique hotel located in the heart of downtown Chicago, within walking distance to many attractions.

Things to Know

  • Be prepared for crowds and long lines at popular attractions.
  • Take advantage of free museum days or discounted tickets with a Chicago CityPASS.
  • Don’t forget to try some deep-dish pizza during your stay!

Transportation

  • Use public transportation: The “L” train (elevated train) and buses are convenient ways to get around the city. You can use a Ventra Card or contactless payment methods.

Day 2: Exploring Chicago’s Neighborhoods

Morning

  • Visit Wicker Park: Explore this trendy neighborhood, known for its vintage shops, independent coffee houses, and street art.
  • Grab breakfast at Big Star: Enjoy tacos and coffee in a fun, retro-style diner.

Lunchtime

  • Eat at Au Cheval: Try their famous burgers (but be prepared for a wait) or explore the surrounding West Town neighborhood for other options.

Afternoon

  • Take a stroll through Lincoln Park: Visit the Lincoln Park Zoo and Conservatory, then walk along the lake shore to North Avenue Beach.
  • Visit the Museum of Contemporary Art: Explore an impressive collection of modern and contemporary art.

Evening

  • Dine at Alinea: Experience avant-garde cuisine from Michelin three-star chef Grant Achatz (reservations recommended).
  • Explore the Logan Square neighborhood: Discover a vibrant nightlife scene with bars, clubs, and live music venues.

Tips and Other Things to Know

  • Be prepared for variable Midwestern weather – pack layers and waterproof gear.
  • Take advantage of free bike rentals or Divvy bike-sharing stations throughout the city.
  • Don’t miss the stunning views from the Signature Room at the 95th floor of the Willis Tower (formerly Sears Tower).

Enjoy your trip to Chicago!