New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Chicago to Milan 3-Day Itinerary Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and River Cruises
Morning
Begin your Chicago adventure with a hearty breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll along the Chicago Riverwalk to admire the city's stunning architecture and make your way to the Chicago River 1.5-Hour Guided Architecture Cruise for a comprehensive tour of the iconic buildings.
Afternoon
For lunch, enjoy the vibrant atmosphere and gourmet tacos at Big Star in Wicker Park. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) and use your skip-the-line ticket to witness breathtaking views of the city and Lake Michigan.
Evening
Savor a delightful dinner at The Signature Room at the 95th, offering panoramic views of Chicago. End your evening with a leisurely walk at The Magnificent Mile, where you can explore the upscale shops and boutiques.
Bedtime
Find amazing hotels in Chicago.
Cultural Explorations and Culinary Delights
Morning
Start your day with a delicious breakfast at Au Cheval, known for its mouthwatering burgers. Then, immerse yourself in art at the Art Institute of Chicago with a fast-pass ticket, allowing you to explore one of the oldest and largest art museums in the country.
Afternoon
Enjoy a diverse range of culinary offerings on the Chicago Favorite Foods Guided Walking Tour. Sample Chicago-style hot dogs, deep-dish pizza, and other local favorites while learning about the city's food history.
Evening
Dine at Girl & the Goat, an award-winning restaurant serving internationally inspired dishes. Afterward, take a relaxing stroll at Navy Pier, where you can enjoy the vibrant atmosphere and stunning lakeside views.
Bedtime
Find amazing hotels in Chicago.
Nature, Science, and Evening Jazz
Morning
Start with breakfast at Lula Cafe, a cozy spot known for its seasonally-inspired dishes. Then, spend your morning at Lincoln Park & Zoo, where you can explore the beautiful park and visit the animals free of charge.
Afternoon
Have lunch at Smoque BBQ, a popular spot for mouthwatering, authentic barbecue. Afterward, visit the Museum of Science and Industry, where you can interact with a variety of fascinating exhibits and learn about scientific innovations.
Evening
Enjoy a sophisticated dinner at RPM Italian, followed by live jazz music at Andy's Jazz Club. It's the perfect way to end your day in Chicago.
Bedtime
Find amazing hotels in Chicago.
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.