New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate Chicago Architecture and Culinary Experience

Ultimate Chicago Architecture and Culinary Experience Itinerary

Last updated: 2024 Jun 14

Iconic Architecture and Deep Dish Delights

Morning
Start your day with a classic Chicago experience at Lou Malnati's Pizzeria, known for its deep-dish pizza. After breakfast, head to the Art Institute of Chicago to admire world-class art collections.
Afternoon
For lunch, savor the flavors of Chicago at Pequod's Pizza, another renowned spot for deep-dish pizza. Afterward, take a stroll down the famous Magnificent Mile for some shopping and sightseeing.
Evening
In the evening, enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. End the night with a visit to the 360 Chicago Observation Deck to see Chicago's skyline at night.
Bedtime
Find amazing hotels in Chicago.
Visit Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

Book Now
Visit The Magnificent Mile in Chicago
star4.65

Magnificent Mile

Book Now
next arrow

River Cruises and Gourmet Dining

Morning
Indulge in a delicious brunch at Au Cheval, known for its upscale diner fare. Afterward, take the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings.
Afternoon
For a unique experience, have lunch at The Purple Pig, a popular Mediterranean restaurant. Afterward, visit the Museum of Science and Industry to explore its interactive exhibits.
Evening
Enjoy a gourmet dinner on a Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, combining sightseeing with fine dining on the water. After the cruise, take a leisurely walk along the Chicago Riverwalk.
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 Museum of Science and Industry in Chicago
star4.31

Museum of Science and Industry

Book Now
next arrow

Architectural Wonders and Culinary Delights

Morning
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Then, embark on the Chicago Architecture River Cruise Skip-the-Ticket Line to see the city's skyline from the water.
Afternoon
For lunch, enjoy a meal at Giordano's, a famous spot for stuffed deep-dish pizza. Afterward, visit the Willis Tower Skydeck and The Ledge to step out onto the glass balcony and feel like you're walking on air.
Evening
Have a memorable dining experience at Alinea, a three-Michelin-star restaurant known for its innovative and artistic dishes. After dinner, take a stroll through Millennium Park to see the iconic Cloud Gate sculpture.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Architecture River Cruise Skip-the-Ticket Line in Chicago
star4.83

Chicago Architecture River Cruise Skip-the-Ticket Line

Book Now
Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago
star4.41

Willis Tower Skydeck and The Ledge

Book Now
next arrow

Top Chicago Travel Videos

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