New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Architectural Marvels and Culinary Delights

Chicago Architectural Marvels and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Iconic Skyline and River Cruise

Morning
Start your day with a delicious brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, head to the Art Institute of Chicago to explore one of the oldest and largest art museums in the country.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Willis Tower Skydeck and The Ledge to get a bird's eye view of the city. Spend the afternoon shopping along The Magnificent Mile.
Evening
In the evening, take a Chicago River Guided Sunset Cocktail & Architecture Tour to admire the city's iconic architecture while enjoying a drink. For dinner, experience contemporary American cuisine at Girl & the Goat.
Bedtime
Find amazing hotels in Chicago.
Visit Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

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

Museum Exploration and Lakefront Dining

Morning
Enjoy a leisurely breakfast at Lula Cafe, a neighborhood spot known for its farm-to-table fare. Then, visit the Field Museum of Natural History to learn about the world's cultures and the environment.
Afternoon
For lunch, indulge in a classic Chicago hot dog at Portillo's Hot Dogs. Afterward, take a relaxing Chicago Lake Michigan Skyline Cruise to enjoy the city's skyline from the water.
Evening
Dine at Alinea, a three-Michelin-star restaurant offering a unique and innovative dining experience. After dinner, take a stroll along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Field Museum of Natural History Ticket or VIP Tour in Chicago
star4.68

Field Museum of Natural History

Book Now
Visit Chicago Lake Michigan Skyline Cruise in Chicago
star4.59

Chicago Lake Michigan Skyline Cruise

Book Now
next arrow

Architectural Wonders and Culinary Gems

Morning
Start your day with a hearty breakfast at Au Cheval, famous for its indulgent burgers and egg dishes. Then, take the Chicago Architecture Center Cruise on Chicago's First Lady for a comprehensive architectural tour.
Afternoon
For lunch, enjoy a taste of Mexico at Xoco, a casual restaurant by award-winning chef Rick Bayless. Afterward, visit the 360 Chicago Observation Deck to see the city from the former John Hancock Center.
Evening
Conclude your trip with a memorable dinner at Alinea, one of the best restaurants in the world. Afterward, take a walk in the vibrant neighborhood of Wicker Park.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Architecture Center Cruise on Chicago's First Lady in Chicago
star4.46

Chicago Architecture Center Cruise on Chicago's First Lady

Book Now
Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago
star4.17

360 Chicago Observation Deck

Book Now

Top Chicago Travel Videos

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