Chicago, Illinois-3-day-itinerary

Chicago 3-Day Itinerary

Day 1: Exploring Downtown Chicago

Morning

  • Start at Millennium Park: Take a stroll through this iconic park and snap a photo in front of the “Cloud Gate” sculpture (also known as “The Bean”).
  • Walk to the nearby Art Institute of Chicago: Spend a few hours exploring the impressive art collection.

Afternoon

  • Take an Architecture River Cruise: Learn about Chicago’s rich architectural history on this 90-minute cruise.
  • Visit the Willis Tower (formerly Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor.

Evening

  • Dine at Lou Malnati’s Pizzeria: Try a classic deep-dish pizza at this Chicago institution.
  • Take a stroll along the Magnificent Mile: Admire the city lights and upscale shops along Michigan Avenue.

Day 2: Museums, Parks, and Food

Morning

  • Visit the Field Museum: Home to Sue, the largest and most complete T. rex skeleton ever found.
  • Explore Lincoln Park Zoo: This free zoo is perfect for families or animal lovers.

Afternoon

  • Walk through the beautiful Lincoln Park: Take in the scenery and visit the Lincoln Park Conservatory and Gardens.
  • Grab lunch at Portillo’s Hot Dogs: Try a classic Chicago-style hot dog or Italian beef sandwich.

Evening

  • Dine at Girl & the Goat: Enjoy Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard.
  • Take a sunset stroll along Lake Shore Path: Enjoy the views of Lake Michigan and the city skyline.

Day 3: Wicker Park, Bucktown, and Logan Square

Morning

  • Explore Wicker Park and Bucktown: Browse vintage shops, record stores, and art galleries in these trendy neighborhoods.
  • Visit the Polish Museum of America: Learn about Polish history and culture in this unique museum.

Afternoon

  • Grab lunch at Big Star Tacos: Enjoy tacos and margaritas in a fun atmosphere.
  • Take a walk along the 606 Trail: This elevated trail offers great views of the city.

Evening

  • Dine at Au Cheval: Try trendy American bistro fare in this popular spot.
  • Catch a show or live music at the Logan Square Auditorium: End your trip with some entertainment in this vibrant neighborhood.

Accommodations

  • The Langham Chicago: Luxuriate in this 5-star hotel with stunning city views.
  • The Robey: Enjoy boutique hotel charm in Wicker Park.
  • Airbnb options: Choose from a range of apartments and homes throughout the city.

Transportation

  • ‘L’ Train (Elevated Train): Conveniently connect to many attractions on this extensive network.
  • Bus: Use the CTA bus system to reach areas not covered by the ‘L’ train.
  • Ride-hailing services: Uber and Lyft operate in Chicago.
  • Walking and biking: Explore neighborhoods on foot or rent a bike through Divvy.

Tips and Essentials

  • Buy a Ventra Card: Load this reusable card with fares for convenient travel on public transportation.
  • Pack layers: Chicago’s weather can be unpredictable, so dress in layers.
  • Tip your servers: Show appreciation for good service at restaurants and bars.
  • Be prepared for crowds: Popular attractions can get busy, plan accordingly.

Other Interests

  • Take a sports tour: Visit iconic stadiums like Wrigley Field (Cubs) or Guaranteed Rate Field (White Sox).
  • Explore street art: Discover vibrant murals and graffiti in the Wicker Park and Bucktown neighborhoods.
  • Visit during festivals: Chicago hosts many festivals throughout the year, such as Lollapalooza, Pitchfork Music Festival, and Taste of Chicago.

Enjoy your trip to Chicago!