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
Family Adventure in Chicago: A 3-Day Itinerary
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
Family Adventure in Chicago: A 3-Day Itinerary
Viewed by 71 travelers
Save This Itinerary
Share
Day 1: Explore Chicago
Chicago, IL on March 19, 2025
8:00AM
Breakfast at Lou Mitchell's
Start your day at this iconic diner known for its hearty breakfasts and delicious sourdough pancakes. Famous among locals and tourists alike, it provides a taste of classic Chicago.
USD15, 1 hour
9:30AM
Visit The Art Institute of Chicago
Explore one of America's oldest and largest art museums, featuring masterpieces from Monet, Van Gogh, and many more. It's a must-see for art lovers.
USD25, 2 hours
12:00PM
Lunch at Giordano's
Enjoy a slice of Chicago's famous deep-dish pizza at Giordano's, known for its stuffed crust that is sure to satiate your hunger.
USD20, 1 hour
1:30PM
Stroll through Millennium Park
Discover the stunning Crown Fountain and the iconic Cloud Gate sculpture, known as 'The Bean', in this vibrant urban park perfect for a relaxing walk.
USD0, 1 hour
2:30PM
Shedd Aquarium
Dive into the aquatic world and explore thousands of marine species at one of the largest indoor aquariums in the world.
USD40, 2 hours
5:00PM
Dinner at The River Roast
Enjoy a riverfront meal at The River Roast, specializing in main-course meats and offering stunning views of the Chicago River.
USD35, 1.5 hours
7:00PM
Chicago River Architecture Cruise
Take an evening boat tour to enjoy the beautiful skyline and learn about the architectural history of Chicago while cruising down the river.
USD40, 1.5 hours
Find Hotels in Chicago
Day 2: Discover Oak Park
Oak Park, IL on March 20, 2025
8:30AM
Breakfast at Poor Phil's
Savor a delicious breakfast with local flair at Poor Phil's, known for its cozy atmosphere and homemade dishes.
USD15, 1 hour
9:30AM
Frank Lloyd Wright Home and Studio
Visit the home and studio of the legendary architect Frank Lloyd Wright, where you can take a guided tour and learn about his innovative designs.
USD15, 2 hours
12:00PM
Lunch at Maneet Chauhan's The Spice Route
Enjoy fusion Indian cuisine in this vibrant restaurant that brings together flavors from across the globe.
USD25, 1 hour
1:30PM
Visit Ernest Hemingway Birthplace
Explore the childhood home of famous author Ernest Hemingway and learn about his early life and literary influence.
USD10, 1.5 hours
3:00PM
Olive Park Trail
Enjoy a leisurely walk or bike ride along this scenic trail that offers beautiful landscapes and local wildlife.
USD0, 1.5 hours
5:00PM
Dinner at Trattoria 225
Taste authentic Italian dishes at Trattoria 225, known for its warm ambiance and delectable pasta options.
USD30, 1.5 hours
Find Hotels in Oak Park
Day 3: Shopping and Relaxation
Schaumburg, IL on March 21, 2025
9:00AM
Breakfast at Egg Harbor Cafe
Start your day with a delicious breakfast at Egg Harbor Cafe, popular for its variety of omelets and fresh fruit options.
USD15, 1 hour
10:00AM
Woodfield Mall Shopping
Spend the morning shopping at one of the largest malls in the United States, featuring over 300 stores for every taste and budget.
USD0, 2.5 hours
12:30PM
Lunch at The Cheesecake Factory
Indulge in a wide variety of dishes and save room for a slice of their famous cheesecake at this popular restaurant.
USD25, 1.5 hours
2:00PM
Visit LEGOLAND Discovery Center
Perfect for families, this indoor family attraction features rides, a 4D cinema, and a giant play area utilizing LEGO bricks.
USD25, 2 hours
4:30PM
Relax at Busse Woods
End your trip with some calming nature at Busse Woods, where you can walk, bike, or just relax amidst beautiful landscapes.
USD0, 1.5 hours
6:00PM
Dinner at Cooper's Hawk Winery and Restaurant
Conclude your adventure with a fine dining experience at Cooper's Hawk, where you can enjoy wine and a range of delectable dishes.
USD40, 2 hours
Find Hotels in Schaumburg
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
Itinerary created by
Plantrip Team
March 18, 2025
AI-assisted, human-reviewed
Plan Your Machesney Park, Il 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