New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Ultimate Chicago Experience: Architecture, Food, and Culture Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your day with a delicious brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a stroll to Millennium Park to see the famous Cloud Gate sculpture.
Afternoon
For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Then, visit the Art Institute of Chicago to admire its world-class art collection.
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
Gangsters, Ghosts, and Food Tasting
Morning
Start your day with a hearty breakfast at Lula Cafe, known for its farm-to-table cuisine. Then, embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's dark history.
Afternoon
For lunch, savor the flavors of Chicago on a Chicago Food, History and Architecture Tour. In the afternoon, visit the Field Museum to explore natural history and anthropology.
Evening
Enjoy a unique dining experience at The Publican, known for its beer selection and pork-centric menu. Conclude your day with a visit to a speakeasy on the Chicago Prohibition Speakeasies Bus Tour or Walking Tour.
Bedtime
Find amazing hotels in Chicago.
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.84Chicago Food, History and Architecture Tour
Book Now
4.84Chicago Food, History and Architecture Tour
Book Now
Sky-High Views and Cultural Immersion
Morning
Have a leisurely breakfast at Little Goat Diner, a cozy spot with a creative menu. Then, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Afternoon
For lunch, enjoy a casual meal at Big Star, known for its tacos and whiskey selection. Spend the afternoon exploring the Chicago Cultural Center and the Chicago Loop.
Evening
Dine at Girl & The Goat, a popular restaurant with a focus on bold flavors. After dinner, attend a performance at the historic Chicago Theatre.
Bedtime
Find amazing hotels in Chicago.
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
Book Now
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
Book Now
4.71Chicago Cultural Center
Book Now
4.71Chicago Cultural Center
Book Now
Museum Day and Lake Michigan Cruise
Morning
Start your day with a classic Chicago breakfast at Xoco, known for its Mexican-inspired dishes. Then, visit the Museum of Science and Industry, a family-friendly museum with interactive exhibits.
Afternoon
For lunch, enjoy a meal at Giordano's, famous for its stuffed deep-dish pizza. In the afternoon, take a Chicago Lake Michigan Skyline Cruise to enjoy the city from the water.
Evening
Dine at Gibsons Bar & Steakhouse, a Chicago institution known for its steaks and seafood. Afterward, take a leisurely walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
4.31Museum of Science and Industry
Book Now
4.31Museum of Science and Industry
Book Now
4.59Chicago Lake Michigan Skyline Cruise
Book Now
4.59Chicago Lake Michigan Skyline Cruise
Book Now
Final Taste of Chicago
Morning
Enjoy a relaxed breakfast at Cafe Ba-Ba-Reeba!, a Spanish tapas restaurant. Spend the morning at the Navy Pier, exploring the shops and attractions.
Afternoon
For lunch, have a taste of Italy at Eataly Chicago, a vibrant marketplace with various dining options. In the afternoon, take a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings.
Evening
Conclude your trip with a memorable dinner at Au Cheval, known for its famous cheeseburger. Afterward, take a final stroll down The Magnificent Mile before heading to the airport.
Bedtime
Find amazing hotels in Chicago.
4.48Navy Pier
Book Now
4.48Navy Pier
Book Now
4.77Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
4.77Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.