Chicago Usa 3 Day Itinerary

3-Day Itinerary for Travelling in Chicago, USA

Day 1: Explore Downtown Chicago

Morning

  • Start at Millennium Park: Begin your day with a stroll through this iconic park, taking in the famous “Cloud Gate” sculpture (also known as “The Bean”) and snapping photos.
  • Take a short walk to the nearby Art Institute of Chicago: Spend a few hours exploring the impressive art collection, including works by Monet, Picasso, and Warhol.

Lunch

  • Try a classic Chicago-style hot dog at Portillo’s: This casual eatery has been serving up delicious dogs since 1963. Don’t forget to add relish, onions, tomatoes, sport peppers, and celery salt!

Afternoon

  • Take an architectural river cruise: Learn about Chicago’s rich history and iconic buildings on a guided boat tour.
  • Visit the Willis Tower (formerly Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor.

Evening

  • Enjoy dinner at Girl & the Goat: This trendy restaurant, owned by Top Chef winner Stephanie Izard, serves creative American cuisine with a focus on seasonal ingredients.
  • Stay at The Kimpton Hotel Monaco Chicago: This stylish hotel is located in the heart of downtown, within walking distance to many attractions.

Day 2: Explore North Side Neighborhoods

Morning

  • Start in Wicker Park: Browse vintage shops and independent boutiques along Milwaukee Avenue.
  • Grab coffee at Intelligentsia Coffee: This popular coffee roaster has several locations throughout the city.

Lunch

  • Try a famous deep-dish pizza at Lou Malnati’s: This family-owned institution has been serving up thick-crusted, cheesy pies since 1975.

Afternoon

  • Visit the Lincoln Park Zoo: Take a stroll through this free zoo, home to over 1,100 animals from around the world.
  • Walk along the Lake Michigan shoreline: Enjoy scenic views of the city skyline and take in the fresh air.

Evening

  • Dine at Alinea: Experience avant-garde, molecular gastronomy at this Michelin three-star restaurant (reservations essential).
  • End the night with live music at The Empty Bottle: This intimate venue features local and national indie rock acts.

Day 3: Explore South Side Attractions

Morning

  • Visit the Museum of Science and Industry: Explore interactive exhibits on science, technology, and innovation.
  • Take a stroll through Hyde Park: Admire the beautiful gardens and architecture of this charming neighborhood.

Lunch

  • Grab a bite at Medici on 57th: This casual eatery serves creative sandwiches, salads, and soups.

Afternoon

  • Tour the University of Chicago campus: Admire the stunning Gothic architecture and take in the intellectual atmosphere.
  • Visit the DuSable Museum of African American History: Learn about the rich history and culture of African Americans at this Smithsonian-affiliated museum.

Evening

  • Enjoy dinner at Blackbird: Savor modern American cuisine with a focus on local, seasonal ingredients.
  • Return to your hotel or explore the nightlife in Wicker Park: End your trip with a nightcap in one of Chicago’s trendiest neighborhoods.

Transportation

  • Use public transportation: The ‘L’ (elevated train) and buses are an efficient way to get around the city. Buy a Ventra Card for easy payment.
  • Ride-hailing services: Uber and Lyft operate in Chicago, but be aware that prices may surge during peak hours.

Tips and Essentials

  • Pack layers: Chicago’s weather can be unpredictable, so dress accordingly.
  • Buy a Chicago CityPASS: This pass grants discounted admission to many attractions, including the Willis Tower and Art Institute of Chicago.
  • Be prepared for crowds: Popular attractions like Millennium Park and Navy Pier can get busy, especially on weekends.
  • Don’t forget sunscreen and sunglasses: Chicago’s summers can be sunny!

Other Things to Know

  • Tipping culture: Aim to tip 15-20% at restaurants and bars.
  • Sales tax: Be prepared for an additional 10.25% sales tax on purchases.
  • Safety: As with any major city, be aware of your surroundings, especially at night.

This itinerary provides a taste of Chicago’s vibrant neighborhoods, iconic attractions, and world-class dining scene. Enjoy your trip to the Windy City!