Plantrip
Sign In
Home
Tools
Create Itinerary
Step-by-Step Builder
Packing List
Travel Expert
Trip Cost Estimator
Weather Expert
Deals
Guides
Pricing
About
About Plantrip
News
Partner Dispatches
Help
Travel Glossary
Sign In
Home
Relaxation and City Experiences in Chicago
Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version
Get new itinerary
Initializing...
0%
Cancel
Step 1 Outline Preview:
PDF
Share
Post
Copy URL
Email this itinerary to someone...
Send Email
Relaxation and City Experiences in Chicago
Viewed by 68 travelers
Save This Itinerary
Share
Day 1: City Exploration
Chicago, USA on August 9, 2024
8:00AM
Breakfast at Yolk
Start your day with a delicious breakfast at Yolk, known for its omelets and pancakes, to energize yourself for a day of exploration.
Head to Millennium Park
$15, 1 hour
10:00AM
Explore Millennium Park
Enjoy the iconic Cloud Gate sculpture 'The Bean,' Crown Fountain, and Lurie Garden in Millennium Park, where art and nature merge seamlessly.
Walk to Maggie Daley Park
Free, 2 hours
12:30PM
Lunch at Cindy's Rooftop
Indulge in a picturesque lunch with panoramic views of the city skyline at Cindy's Rooftop located on top of the Chicago Athletic Association Hotel.
Head to Navy Pier
$30, 1.5 hours
3:00PM
Explore Navy Pier
Spend your afternoon at Navy Pier, taking a ride on the Ferris wheel, visiting the Chicago Children's Museum, and enjoying the lakefront views.
End the day with dinner at Giordano's for their famous deep-dish pizza
$25, 2 hours
Find Hotels in Chicago
Day 2: Art and Shopping
Chicago, USA on August 10, 2024
9:00AM
Visit Art Institute of Chicago
Explore one of the oldest and largest art museums in the United States, housing iconic works like Grant Wood's 'American Gothic' and Seurat's 'A Sunday on La Grande Jatte.'
Walk to Riverwalk
$25, 3 hours
1:00PM
Lunch at City Winery
Enjoy a leisurely lunch at City Winery along the Chicago Riverwalk, pairing delicious food with their own locally made wines.
Stroll along The Magnificent Mile
$40, 2 hours
4:00PM
Explore The Magnificent Mile
Shop at upscale boutiques, department stores, and luxury retailers on this prestigious shopping avenue, known for its iconic architecture.
End the day with dinner at RPM Italian for modern Italian cuisine
$50, 2 hours
Find Hotels in Chicago
Day 3: Nature and Views
Chicago, USA on August 11, 2024
8:00AM
Breakfast at The Allis
Start your day with a chic breakfast at The Allis, offering a relaxed ambiance and delectable morning menu options.
Head to Lincoln Park
$20, 1 hour
10:00AM
Explore Lincoln Park
Visit Lincoln Park Zoo, stroll through the green spaces, and admire the historic architecture in this charming neighborhood.
Travel to Chicago Botanic Garden
$30, 3 hours
2:00PM
Visit Chicago Botanic Garden
Immerse yourself in the beauty of nature at the Chicago Botanic Garden, featuring diverse gardens and landscapes to explore.
Head to Skydeck Chicago
$30, 2 hours
5:00PM
Experience Skydeck Chicago
Marvel at panoramic views of the city from the Skydeck, especially during sunset, for an unforgettable perspective of Chicago's skyline.
Conclude your day with dinner at Alinea, a top-rated fine dining restaurant
$150, 2 hours
Find Hotels in Chicago
0
Travel Requirements
Local Sayings
Connectivity Info
Nearby Shopping
Accepted Currency + Payment Types
Safety
Cultural Norms + Etiquette
Health + Medical Facilities
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
PDF
Share
Post
Copy URL
Email this itinerary to someone...
Send Email
More About Chicago
Trip Packing List: Chicago (Late February 2026)
Packing List
Trip Packing List: Ahmedabad → Abu Dhabi → Chicago (4 Jun–11 Jul)
Packing List
Chicago Weather Guide: Mid-May Transitions & Lake Breezes
Weather Guide
Chicago Weather & Climate Guide: Seasons in the Windy City
Weather Guide
Full Guide to Michelin Star Cities: 2025 Updated List
Travel Expert
Global Michelin Cities & US Travel Tiers from New York
Travel Expert
Itinerary created by
Plantrip Team
June 24, 2024
AI-assisted, human-reviewed
Plan Your Chicago Trip
Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go
Unlock Unlimited Trips
$2.50
/mo
Billed $30/year
Unlimited trip generations
Personalized packing lists
Extra details & local tips
Private & ad-free
Sign In to Upgrade
See all plans
Upgrade to Plus
$2.50
/mo
Billed $30/year
Unlimited trip generations
Personalized packing lists
Extra details & local tips
Private & ad-free
Sign In to Upgrade
See all plans
Sign in to save this itinerary.
Sign Up
or
Sign In
Create a Free Account
Sign up for free to keep generating itineraries!
Sign Up Free
I already have an account
Trip Locations
Share Itinerary
PDF
Share
Post
Copy URL
Email this itinerary to someone...
Send Email