New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Architectural Marvels and Deep Dish Delights in Chicago

Architectural Marvels and Deep Dish Delights in Chicago Itinerary

Last updated: 2024 Jun 14

Iconic Architecture and Deep Dish Debut

Morning
Start your architectural exploration at the renowned The Art Institute of Chicago, where you can admire a world-class collection. Afterward, take a leisurely walk to Millennium Park to see the famous Cloud Gate sculpture.
Afternoon
For lunch, savor your first taste of deep dish pizza at Lou Malnati's Pizzeria, a local favorite. Afterward, continue your architectural journey with a visit to the Wrigley Building and a stroll along the Chicago Riverwalk.
Evening
In the evening, enjoy a sunset cocktail on a Chicago River Guided Sunset Cocktail & Architecture Tour, where you can appreciate the city's skyline from the water. End the day with a delightful dinner at The Purple Pig, known for its Mediterranean-inspired small plates.
Bedtime
Find amazing hotels in Chicago.

Museum Marvels and Gourmet Discoveries

Morning
Begin your day with a visit to the Field Museum, home to a fascinating collection of natural history exhibits. Afterward, take a walk in Grant Park.
Afternoon
For lunch, indulge in a gourmet experience at Alinea, a three-Michelin-star restaurant. Afterward, continue to the Adler Planetarium to explore the wonders of the universe.
Evening
In the evening, enjoy a sophisticated dining experience at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. After dinner, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn more about the city's iconic buildings.
Bedtime
Find amazing hotels in Chicago.

Sky-High Views and Cultural Delights

Morning
Start your day with a bird's eye view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). After taking in the panoramic sights, explore the vibrant neighborhood of The Magnificent Mile.
Afternoon
For lunch, enjoy a meal at Girl & the Goat, a popular spot for creative cuisine. Afterward, visit the Chicago Cultural Center to admire the stunning architecture and art exhibitions.
Evening
Dine at Au Cheval, known for its famous burger, to experience a true Chicago culinary delight. After dinner, take a leisurely walk along the Chicago River to see the city lights reflected on the water.
Bedtime
Find amazing hotels in Chicago.

Final Flavors and Farewell to Chicago

Morning
Spend your last morning in Chicago at Navy Pier, where you can enjoy the attractions and lake views. Don't miss a ride on the Chicago Navy Pier Centennial Wheel.
Afternoon
For your final meal, savor the flavors of Mexico at Rick Bayless' Frontera Grill. After lunch, take a Chicago River 1.5-Hour Guided Architecture Cruise to bid farewell to the city's stunning skyline.
Evening
Conclude your Chicago experience with a visit to The Signature Room at the 95th for a drink with a view. Reflect on your architectural and culinary journey through the Windy City before heading to the airport.
Bedtime
Find amazing hotels in Chicago.

Top Chicago Travel Videos

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