New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Ultimate Chicago Experience: Architecture, Cuisine, and Culture Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a stroll along the Millennium Park to see the famous Cloud Gate sculpture.
Afternoon
For lunch, savor the deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to admire its world-class art collection.
Evening
In the evening, enjoy a gourmet dinner at Alinea, a three-Michelin-star restaurant. Afterward, take a Chicago River Guided Sunset Cocktail & Architecture Tour to see the city's skyline light up.
Bedtime
Find amazing hotels in Chicago.
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
Culinary Delights and Navy Pier Adventure
Morning
Indulge in a delicious brunch at Lula Cafe, known for its farm-to-table cuisine. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's architecture.
Afternoon
Evening
Enjoy a seafood dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, catch a show at the Chicago Theatre.
Bedtime
Find amazing hotels in Chicago.
4.46Chicago Architecture Center Cruise on Chicago's First Lady
Book Now
4.46Chicago Architecture Center Cruise on Chicago's First Lady
Book Now
4.48Navy Pier
Book Now
4.48Navy Pier
Book Now
Museum Day and Skydeck Views
Morning
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe. Then, visit the Field Museum of Natural History to explore exhibits on natural history and culture.
Afternoon
For lunch, enjoy a taste of Italy at Eataly Chicago. Afterward, head to the Willis Tower Skydeck and The Ledge to get panoramic views of the city.
Evening
Dine at Girl & the Goat, a popular spot for inventive cuisine. End your day with a leisurely walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
4.68Field Museum of Natural History
Book Now
4.68Field Museum of Natural History
Book Now
4.41Willis Tower Skydeck and The Ledge
Book Now
4.41Willis Tower Skydeck and The Ledge
Book Now
Gangsters, Ghosts, and Local Brews
Morning
Enjoy a relaxed breakfast at Little Goat Diner, a diner with a creative twist. Then, embark on a Chicago Discover the Gangsters & Ghosts of the City's Past tour to learn about the city's dark history.
Afternoon
For lunch, try the famous pastrami sandwich at Manny's Cafeteria & Delicatessen. Afterward, take a break at Millennium Park and visit the Cloud Gate.
4.68Chicago Discover the Gangsters & Ghosts of the City's Past
Book Now
4.68Chicago Discover the Gangsters & Ghosts of the City's Past
Book Now
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
Farewell to Chicago: Brunch and Cultural Gems
Morning
Enjoy a leisurely brunch at Longman & Eagle, a Michelin-starred gastropub. Afterward, take a walk in the historic Wicker Park neighborhood.
Afternoon
Spend your final afternoon visiting the Chicago Cultural Center and the Rookery Building. For a late lunch, try the famous hot dogs at Portillo's Hot Dogs.
Evening
End your Chicago adventure with a memorable dinner at Au Cheval, home to one of the best burgers in the city. Reflect on your trip as you take a final walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
4.71Chicago Cultural Center
Book Now
4.71Chicago Cultural Center
Book Now
4.31Rookery Building
Book Now
4.31Rookery Building
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.