New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate Chicago Experience in 3 Days

Ultimate Chicago Experience in 3 Days Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning
Start your day with a delightful breakfast at Lula Cafe, known for its cozy atmosphere and delicious dishes. Afterward, head to the Art Institute of Chicago to immerse yourself in a world of art and culture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, take a stroll along the Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean."
Evening
In the evening, enjoy a scenic Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's stunning architecture. After the cruise, have a memorable dinner at The Signature Room at the 95th, offering panoramic views of the city.
Bedtime
Find amazing hotels in Chicago.
activity-image

Art Institute of Chicago

star4.61

click to access prices

activity-image

Millennium Park

star4.69

click to access prices

activity-image

Chicago River 1.5-Hour Guided Architecture Cruise

star4.77

click to access prices

Museum and Skydeck Experience

Morning
Start your day with a delicious brunch at Little Goat Diner, a popular spot for its creative menu. Afterward, visit the Field Museum of Natural History to explore the natural world and ancient civilizations.
Afternoon
For a thrilling experience, head to the Chicago Willis Tower Skydeck and The Ledge Ticket to enjoy panoramic views of the city. After taking in the sights, have a late lunch at Giordano's, known for its stuffed deep-dish pizza.
Evening
In the evening, take a Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city at dusk. Conclude your day with a dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse.
Bedtime
Find amazing hotels in Chicago.
activity-image

Chicago Field Museum of Natural History Ticket or VIP Tour

star4.68

click to access prices

activity-image

Chicago Willis Tower Skydeck and The Ledge Ticket

star4.41

click to access prices

activity-image

Chicago River Guided Sunset Cocktail & Architecture Tour

star4.24

click to access prices

Cultural Exploration and Navy Pier

Morning
Enjoy a leisurely breakfast at Au Cheval, famous for its decadent burgers. Then, take a walk through the Chicago Cultural Center, known for its stunning architecture and cultural exhibitions.
Afternoon
For lunch, indulge in Spanish tapas at Cafe Ba-Ba-Reeba!. Afterward, spend the afternoon at Navy Pier, where you can ride the Centennial Wheel and enjoy the waterfront views.
Evening
Conclude your Chicago adventure with a dinner at Girl & The Goat, a renowned restaurant offering a creative menu. After dinner, take a relaxing evening stroll along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
activity-image

Chicago Cultural Center

star4.71

click to access prices

activity-image

Navy Pier

star4.48

click to access prices

activity-image

Chicago Riverwalk

star4.72

click to access prices

Top Chicago Travel Videos

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