New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

7-Day Architecture and Culinary Exploration in Chicago Itinerary

Last updated: 2024 Jun 14

Iconic Skyscrapers and River Cruise

Morning

Start your architectural journey with a visit to the iconic Willis Tower Skydeck. Enjoy panoramic views of the city and step out onto The Ledge for a thrilling experience.

Afternoon

For lunch, savor deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Afterward, take a Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's skyline.

Evening

Dine at The Signature Room at the 95th, offering a fine dining experience with stunning views from the John Hancock Center.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.41
Willis Tower
Book Now

4.77
Chicago River 1.5-Hour Guided Architecture Cruise
Book Now

Museum Campus and Lakefront Architecture

Morning

Explore the Field Museum and the Shedd Aquarium on Museum Campus, both architectural gems.

Afternoon

Enjoy a gourmet lunch on a Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise, combining great food with views of the city's architecture from the water.

Evening

Have dinner at Gibsons Bar & Steakhouse, a Chicago institution known for its classic dishes.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.56
Field Museum
Book Now

4.75
Shedd Aquarium
Book Now

Art and Culture in the City

Morning

Visit the Art Institute of Chicago and explore its impressive architectural design and world-class art collection.

Afternoon

For a late lunch, experience the vibrant atmosphere of Xoco, offering delicious Mexican cuisine by a renowned chef.

Evening

Attend a show at The Chicago Theatre, known for its iconic marquee and stunning interior.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.61
Art Institute of Chicago
Book Now

4.71
The Chicago Theatre
Book Now

Innovative Architecture and Culinary Delights

Morning

Discover the unique architecture of the Modern Wing at the Art Institute of Chicago, a striking contrast to the historic building.

Afternoon

Enjoy a progressive dining experience at Alinea, one of the world's best restaurants, known for its innovative cuisine and design.

Evening

Take a leisurely walk along the Chicago Riverwalk and admire the city's architecture illuminated at night.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.61
Modern Wing at the Art Institute of Chicago
Book Now

4.72
Chicago Riverwalk
Book Now

Neighborhood Gems and Culinary Diversity

Morning

Explore the architecture of the Wrigley Building and the Tribune Tower on the Magnificent Mile.

Afternoon

Have a relaxed lunch at Lula Cafe in the vibrant Logan Square neighborhood, known for its farm-to-table cuisine.

Evening

Indulge in a multi-course tasting menu at Girl & the Goat, a top-rated restaurant offering a creative blend of flavors.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.39
Wrigley Building
Book Now

4.61
Tribune Tower
Book Now

Architectural Diversity and Culinary Icons

Morning

Visit the historic Robie House in Hyde Park, designed by Frank Lloyd Wright, a masterpiece of Prairie School architecture.

Afternoon

Enjoy a late lunch at Au Cheval, famous for its decadent burger, a must-try in Chicago.

Evening

Dine at Alinea, a three-Michelin-star restaurant known for its avant-garde cuisine and architectural presentation.

Bedtime

Find amazing hotels in Chicago, Illinois.

Culinary and Architectural Farewell

Morning

Take a final stroll through the Millennium Park and admire the architecture of the Cloud Gate, also known as "The Bean."

Afternoon

Enjoy a farewell lunch at The Purple Pig, a popular spot for its Mediterranean-inspired small plates.

Evening

Conclude your trip with a sunset cocktail on a Chicago River Guided Sunset Cocktail & Architecture Tour, toasting to the architectural wonders of the city.

Bedtime

Find amazing hotels in Chicago, Illinois.