New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Adventure - 6 Days

Chicago Adventure - 6 Days Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning
Start your Chicago adventure with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (The Bean) and offers beautiful gardens and art installations. It's a great way to get acquainted with the city's vibrant atmosphere.
Afternoon
Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world. For lunch, enjoy a meal at The Purple Pig, known for its delicious Mediterranean-inspired dishes.
Evening
End your day with a relaxing stroll along Chicago Riverwalk. This scenic pathway along the Chicago River offers stunning views of the city's architecture. For dinner, indulge in some deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic.
Bedtime
Find amazing hotels in Chicago, Illinois.

Exploring Chicago's Icons

Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of the tallest buildings in the Western Hemisphere. Afterward, grab breakfast at Wildberry Pancakes and Cafe, famous for its delicious pancakes and brunch options.
Afternoon
Spend your afternoon at Field Museum, where you can explore fascinating exhibits on natural history and ancient civilizations. For lunch, head to Portillo's Hot Dogs for some classic Chicago-style hot dogs and Italian beef sandwiches.
Evening
In the evening, catch a show at Chicago Theatre, an iconic venue known for its stunning architecture and world-class performances. For dinner, treat yourself to an unforgettable dining experience at Alinea, one of Chicago's most renowned restaurants.
Bedtime
Find amazing hotels in Chicago, Illinois.

Cultural Gems & Culinary Delights

Morning
Start your day with a visit to Museum of Science and Industry, one of the largest science museums in the world. Explore interactive exhibits that are both educational and entertaining.
Afternoon
Afterward, take a leisurely walk through Grant Park, often referred to as "Chicago's front yard." Enjoy its beautiful gardens and fountains before heading to lunch at Giordano's for another taste of deep-dish pizza.
Evening
In the evening, immerse yourself in live music at House of Blues. This iconic venue offers fantastic performances across various genres. For dinner, savor some mouthwatering BBQ at Smoque BBQ.
Bedtime
Find amazing hotels in Chicago, Illinois.

Architectural Wonders & Scenic Views

Morning
Kick off your day with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of Lake Michigan and downtown Chicago from this iconic skyscraper.
Afternoon
Next up is a tour through historic architecture by visiting both  Rookery Building and Chicago Board of Trade Building for their stunning designs. Stop by The Publican for lunch featuring farm-to-table cuisine.
Evening
Conclude your day by exploring Navy Pier’s attractions including rides or simply enjoying lakefront views while dining on seafood specialties found only here like those offered by Shaw’s Crab House
Bedtime
Find amazing hotels in Chicago, Illinois.

History and Entertainment

Morning
Begin your day with a visit to Lincoln Park & Zoo. This free zoo is one of the oldest in the country and offers a great way to enjoy the morning while learning about various animals. Afterward, have breakfast at Big Star, known for its delicious tacos and vibrant atmosphere.
Afternoon
Spend your afternoon exploring Field Museum, where you can delve into fascinating exhibits on natural history and ancient civilizations. For lunch, head to RPM Italian for some exquisite Italian cuisine.
Evening
In the evening, catch a game or concert at United Center, home to the Chicago Bulls and Blackhawks. For dinner, treat yourself to a meal at Gibsons Bar & Steakhouse, famous for its prime steaks and classic American fare.
Bedtime
Find amazing hotels in Chicago, Illinois.

Farewell Chicago

Morning
Adler Planetarium is a perfect start for your final day in Chicago. Enjoy interactive exhibits and stunning views of Lake Michigan. Have breakfast at Wildberry Pancakes and Cafe for their renowned pancakes.
Afternoon
Navy Pier offers various attractions including rides, shops, and beautiful lakefront views. For lunch, stop by Eataly Chicago for an authentic Italian dining experience with multiple food stations.
Evening
Chicago River provides a serene end to your trip with an evening boat tour along the river. Conclude your journey with dinner at The Publican, known for its farm-to-table cuisine and lively atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois.
kayakFind the right stay during your trip.
Got a question about your trip?