New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Adventure: River Cruises, Skyline Views & Culinary Delights

Chicago Adventure: River Cruises, Skyline Views & Culinary Delights Itinerary

Last updated: 2024 Jun 14

Riverfront Marvels & Sky-High Thrills

Morning
Start your day with a delightful breakfast at Lula Cafe, known for its farm-to-table fare. Then, embark on the Chicago River 1.5-Hour Guided Architecture Cruise, immersing yourself in the city's stunning architecture. After the cruise, visit the iconic Wrigley Building and take a leisurely stroll along the Chicago Riverwalk.
Afternoon
For lunch, savor the flavors of Chicago at Pequod's Pizza, famous for its deep-dish pies. Post-lunch, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city. Cap off the afternoon with a visit to the The Magnificent Mile for some shopping and sightseeing.
Evening
Enjoy a scrumptious dinner at Girl & The Goat, a renowned spot for innovative cuisine. Conclude your day with a visit to the 360 Chicago Observation Deck Sip and View Ticket, where you can sip on cocktails while admiring the city lights.
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 Wrigley Building in Chicago
star4.39

Wrigley Building

Book Now
next arrow

Cultural Gems & Culinary Delights

Morning
Indulge in a delectable brunch at Little Goat Diner, a favorite among locals. Then, explore the Art Institute of Chicago, home to a world-class collection of art. Afterward, take a leisurely walk through Millennium Park and marvel at the iconic Cloud Gate.
Afternoon
For lunch, head to Giordano's for their famous stuffed deep-dish pizza. Post-lunch, visit the Field Museum to delve into natural history and anthropology. Later, take a relaxing Chicago Lake Michigan Skyline Cruise to enjoy the city's skyline from the water.
Evening
Treat yourself to a memorable dinner at Gibsons Bar & Steakhouse, known for its prime steaks and lively atmosphere. Conclude your day with a visit to the historic Chicago Theatre for a show or a photo op at the iconic marquee.
Bedtime
Find amazing hotels in Chicago.
Visit Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

Book Now
Visit Millennium Park in Chicago
star4.69

Millennium Park

Book Now
next arrow

Adventurous Explorations & Farewell Feasts

Morning
Start your day with a hearty breakfast at Portillo's Hot Dogs, a Chicago institution. Then, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history. After the tour, visit the Navy Pier for a leisurely walk and some fun at the Centennial Wheel.
Afternoon
Enjoy a late lunch at Kuma's Corner, known for its unique burgers and metal-themed ambiance. Post-lunch, visit the Shedd Aquarium to explore the wonders of the aquatic world. End your afternoon with a visit to the Adler Planetarium for a celestial experience.
Evening
Conclude your Chicago adventure with a farewell dinner at The Signature Room at the 95th, where you can enjoy exquisite cuisine with a view. After dinner, take a stroll along the Chicago Riverwalk to soak in the city's evening ambiance.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago
star4.68

Chicago Gangsters and Ghosts Guided Walking Tour

Book Now
Visit Navy Pier in Chicago
star4.48

Navy Pier

Book Now
next arrow

Top Chicago Travel Videos

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