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 2-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 2-Day Itinerary
Viewed by 100 travelers
Save This Itinerary
Share
Day 1: Exploring Downtown
Chicago, USA
8:00AM
Breakfast at Wildberry Pancakes and Cafe
Start your day with delicious pancakes and fresh fruit at Wildberry, a favorite among families.
Located near Millennium Park, just a short walk away.
USD 50, 1 hour
9:30AM
Visit Millennium Park
After breakfast, take a stroll in Millennium Park to see the iconic Cloud Gate (The Bean) and enjoy the outdoor spaces.
Walk from the cafe to Millennium Park, it’s a quick 15-minute stroll.
Free, 1.5 hours
11:00AM
Explore the Art Institute of Chicago
Immerse yourself in the rich collection of artwork at the Art Institute, a great way to spark the kids' creativity.
From Millennium Park, it’s a 10-minute walk.
USD 40, 2 hours
1:00PM
Lunch at Giordano's
Grab a classic Chicago deep-dish pizza at Giordano's, which will surely please the whole family.
A 5-minute walk from the Art Institute.
USD 70, 1.5 hours
2:30PM
Visit the Shedd Aquarium
Spend your afternoon enjoying the fascinating marine life at the Shedd Aquarium, which offers interactive exhibits for children.
Take a bus or rideshare from Giordano's, which takes about 15 minutes.
USD 80, 2 hours
5:00PM
Relax at Millennium Park
Head back to Millennium Park and let the kids play in the Crown Fountain while you enjoy a little downtime.
Take a short bus ride back to Millennium Park.
Free, 1 hour
6:00PM
Dinner at Portillo's
Savor Chicago's famous hot dogs and Italian beef sandwiches for dinner at Portillo's.
Easily accessible via public transport from Millennium Park, approximately 15 minutes.
USD 60, 1.5 hours
7:30PM
Evening Riverwalk Stroll
Enjoy a leisurely walk along the Chicago Riverwalk, taking in the city lights and views.
Walk from Portillo's which is about a 20-minute stroll.
Free, 1 hour
Find Hotels in Chicago
Day 2: Adventure and Fun
Chicago, USA
8:00AM
Breakfast at Lou Mitchell's
Fuel up with a hearty breakfast at Lou Mitchell's, known for its friendly atmosphere and delicious offerings.
Located a short drive or a bus ride from your hotel.
USD 50, 1 hour
9:30AM
Visit the Field Museum
Discover fascinating exhibits, including Sue the T.rex, at the Field Museum, which is both fun and educational for kids.
A 15-minute bus ride from the restaurant.
USD 60, 2.5 hours
12:00PM
Lunch at The Field Bistro
Enjoy a casual lunch at The Field Bistro, located within the museum, for a stress-free dining experience.
Conveniently located in the Field Museum.
USD 50, 1 hour
1:00PM
Explore the Museum of Science and Industry
Continue your adventure at the Museum of Science and Industry, where interactive exhibits will engage kids and adults alike.
A short taxi ride or 30-minute public transit trip.
USD 44, 2.5 hours
3:30PM
Play at Grant Park
Wind down and let the kids run around at Grant Park, a magnificent green space in the heart of downtown.
Take a 20-minute walk from the Museum.
Free, 1 hour
4:30PM
Dinner at Maggiano's Little Italy
Enjoy family-style dining at Maggiano's, where everyone can share a variety of Italian dishes.
A short walk from Grant Park, around 10 minutes.
USD 100, 1.5 hours
6:00PM
Chicago River Evening Cruise
End your day with a relaxing river cruise, providing stunning views of Chicago's iconic skyline.
Head to the riverboats located a short distance from Maggiano's.
USD 80, 1.5 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
July 25, 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