New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate 3-Day Chicago Architecture and Culinary Experience

Ultimate 3-Day Chicago Architecture and Culinary Experience Itinerary

Last updated: 2024 Jun 14

Iconic Architecture and Gourmet Delights

Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a Chicago River 1.5-Hour Guided Architecture Cruise to marvel at the city's skyline.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to appreciate a world-class art collection.
Evening
In the evening, enjoy a sophisticated dinner at Alinea, a three-Michelin-star restaurant offering a unique culinary experience.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago
star4.77

Chicago River 1.5-Hour Guided Architecture Cruise

Book Now
Visit Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

Book Now

Sky-High Views and Cultural Immersion

Morning
Indulge in a classic Chicago breakfast at Lula Cafe, known for its farm-to-table dishes. Afterward, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Afternoon
For lunch, experience the vibrant atmosphere of Big Star while enjoying authentic Mexican street food. Then, immerse yourself in the city's history at the Chicago History Museum.
Evening
Dine at Girl & the Goat, a popular spot for creative small plates. Afterward, catch a show at the iconic Chicago Theatre.
Bedtime
Find amazing hotels in Chicago.
Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago
star4.17

360 Chicago Observation Deck (Formerly John Hancock Observatory)

Book Now
Visit Chicago Theatre in Chicago
star4.71

Chicago Theatre

Book Now

Final Taste of Chicago's Best

Morning
Enjoy a leisurely brunch at Little Goat Diner, a favorite for its comfort food with a twist. Afterward, take a walk in Millennium Park and see the famous Cloud Gate sculpture.
Afternoon
For your last Chicago meal, savor the Italian dishes at RPM Italian, a celebrity-owned restaurant. Then, take a relaxing Chicago Riverwalk to soak in the city's atmosphere.
Evening
End your Chicago culinary journey with a classic Chicago-style hot dog at Portillo's Hot Dogs. Before you leave, enjoy a cocktail at the Signature Lounge in the John Hancock Center, taking in the city lights.
Bedtime
Find amazing hotels in Chicago.
Visit Millennium Park in Chicago
star4.69

Millennium Park

Book Now
Visit Chicago Riverwalk in Chicago
star4.72

Chicago Riverwalk

Book Now

Top Chicago Travel Videos

kayakFind the right stay during your trip.
Got a question about your trip?