Chicago Usa 3 Day Itinerary

Title: Chicago 3-Day Itinerary

Day 1 - Exploring Downtown Chicago

  • Morning: Start your day with breakfast at Amy’s Café & Bookstore, a charming café offering delicious breakfast options and a vast collection of books.

  • Afternoon: Visit the iconic Navy Pier for stunning lake views, fun attractions like the Centennial Wheel, and boat tours. Grab lunch at Pizano’s Pizza & Pasta, a popular spot for deep-dish pizza.

  • Afternoon/Evening: Explore Millennium Park and The Bean (Cloud Gate). Don’t miss the stunning architecture of Frank Gehry’s Jay Pritzker Pavilion. Head to The Art Institute of Chicago, one of the oldest and largest art museums in the U.S. For dinner, dine at Girl & The Goat, a Michelin-starred restaurant offering innovative small plates.

Day 2 - Architecture and Museums

  • Morning: Begin with breakfast at The Waffle Stop, serving up delicious sweet and savory waffles.

  • Afternoon: Take a guided Architecture River Cruise to learn about Chicago’s iconic buildings. Lunch can be had at Lou Malnati’s Pizzeria, another famous spot for deep-dish pizza.

  • Afternoon/Evening: Visit the Museum of Science and Industry, one of the largest science museums in the world. Dinner can be enjoyed at Alinea, a three-Michelin-star restaurant known for its innovative cuisine.

Day 3 - Neighborhood Exploration

  • Morning: Have breakfast at Ann Sather’s Bakery, offering a variety of breakfast dishes and pastries.

  • Afternoon: Head to Wicker Park, a trendy neighborhood filled with independent shops, art galleries, and cafes. Visit the Wicker Park Bucktown Chamber of Commerce for a map of local attractions. Lunch at Big Star, serving up Tex-Mex cuisine.

  • Afternoon/Evening: Explore Lincoln Park Zoo and the nearby Lincoln Park Conservatory. For dinner, dine at The Purple Pig, offering a selection of Mediterranean dishes and cheeses.

Things to Know

  • Chicago’s public transportation system is extensive and easy to navigate with the Chicago Transit Authority (CTA). Purchase a Ventra card for unlimited travel.

  • The city can be chilly, especially in spring and fall, so pack layers!

  • Many attractions offer discounted tickets or packages, so do your research to save money.

Where to Stay