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 Lou Malnati's Pizzeria, known for its deep-dish pizza. Afterward, head to The Magnificent Mile for some shopping and to admire the architecture.
Afternoon
For lunch, savor the famous burgers at Au Cheval. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning views of the city.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th and then take a Chicago River Guided Sunset Cocktail & Architecture Tour to see the city's skyline light up.
Bedtime
Find amazing hotels in Chicago.
Visit The Magnificent Mile in Chicago
star4.65

The Magnificent Mile

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

360 Chicago Observation Deck (Formerly John Hancock Observatory)

Book Now
next arrow

Culinary Delights and Cultural Immersion

Morning
Indulge in a brunch at Alinea, a three-Michelin-star restaurant. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's architecture.
Afternoon
For a unique experience, have a late lunch at Girl & the Goat, known for its bold flavors. Then, explore the Art Institute of Chicago at your own pace.
Evening
Enjoy a progressive dinner at Eataly Chicago, where you can sample a variety of Italian dishes. Afterward, take a leisurely walk along the Chicago Riverwalk.
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 Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

Book Now
next arrow

Museum and Science Exploration

Morning
Start your day with a classic Chicago breakfast at The Purple Pig. Then, visit the Field Museum to immerse yourself in natural history.
Afternoon
For lunch, enjoy the vibrant atmosphere at Big Star and savor their tacos. Afterward, explore the Museum of Science and Industry, a hands-on learning experience for all ages.
Evening
Conclude your trip with a dinner at Gibsons Bar & Steakhouse, a Chicago institution. Then, take a leisurely stroll in Grant Park to admire the city's skyline.
Bedtime
Find amazing hotels in Chicago.
Visit Field Museum in Chicago
star4.56

Field Museum

Book Now
Visit Museum of Science and Industry in Chicago
star4.31

Museum of Science and Industry

Book Now
next arrow

Top Chicago Travel Videos

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