Chicago Usa 4 Day Itinerary

Chicago 4-Day Itinerary: Exploring the Windy City

Day 1: Downtown Chicago

Morning:

  • Check-in at your hotel (recommended: The Langham, Chicago or The Ritz-Carlton, Chicago)
  • Breakfast at Ann Sather’s Bakery & Café, known for their cinnamon rolls and omelets.

Afternoon:

  • Visit Navy Pier, home to the Centennial Wheel, Chicago Children’s Museum, and numerous shops and restaurants.
  • Explore Millennium Park and don’t miss the iconic “Bean” sculpture (Cloud Gate).
  • Lunch at Girl & The Goat, a popular spot for innovative small plates. Reservations recommended!

Evening:

  • Take a cruise on Lake Michigan with Wendella Sightseeing Cruises or Shoreline Sightseeing.
  • Dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse.

Day 2: Museums and Architecture Tour

Morning:

  • Breakfast at The Breakfast Club or Amy’s Café & Bookstore.
  • Visit The Art Institute of Chicago, home to over 300,000 works spanning 5,000 years.

Afternoon:

  • Lunch at Lou Malnati’s Pizzeria or Gioia’s Deli for a taste of deep-dish pizza.
  • Take an architecture river cruise with Chicago Architecture Center to learn about the city’s iconic buildings.

Evening:

  • Dinner at Alinea, one of the world’s top restaurants. Reservations months in advance are recommended!
  • Cocktails at The Signature Room on the 95th floor of the John Hancock Building for stunning views of Chicago.

Day 3: Lincoln Park and Wrigleyville

Morning:

  • Breakfast at Flour Child Bakery.
  • Visit the Lincoln Park Zoo or the Lincoln Park Conservatory.

Afternoon:

  • Lunch at Frontera Grill by celebrity chef Rick Bayless.
  • Take a stroll through DePaul University’s campus.

Evening:

  • Visit Wrigley Field, home of the Chicago Cubs, for a game (if in season) or a tour.
  • Dinner at Gordon for contemporary American cuisine.

Day 4: Neighborhood Exploration

Morning:

  • Breakfast at The HandleBar, a bicycle-themed café.
  • Visit Bucktown and Wicker Park neighborhoods, known for their unique shops, street art, and vibrant nightlife.

Afternoon:

  • Lunch at Au Cheval, one of the city’s best burger spots.
  • Take a stroll along The 606, a elevated park built on an old railway line.

Evening:

  • Dinner at GreenRiver for stunning views and innovative cuisine.
  • End your trip with drinks at Three Dots and a Dash, a tiki bar with tropical cocktails.

Transportation:

  • Chicago Transit Authority (CTA) offers extensive bus and train service throughout the city, including the famous “L” trains.
  • Divvy bike-sharing is also available for exploring the neighborhoods.

Things to Know:

  • Chicago is known for its strong winds, so dress accordingly!
  • Tipping in Chicago is customary at restaurants and bars (18-20%).
  • Sales tax in Illinois is 9.25%, so prices may include this already.
  • Reservations are recommended for popular restaurants, especially during peak travel seasons.

Tips:

  • Don’t miss the Chicago Riverwalk for a scenic stroll along the water.
  • Take a selfie with “The Lurie Garden” (a beautiful public garden) in the background for an iconic Chicago photo!
  • Explore the city’s vibrant neighborhoods like Ravenswood, Pilsen, and Logan Square to get a feel for local life.

Enjoy your trip to Chicago, and remember to “Keep It Moving” (Chicago’s motto) as you discover all the city has to offer!