Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

25-Day Chicago and Indiana Adventure

Viewed by 66 travelers

Day 1: Arrival in Chicago

Chicago, IL on March 16, 2025

9:00 AM

Breakfast at Lou Mitchell's

Start your day with a classic Chicago breakfast at Lou Mitchell's, famous for its pancakes and complimentary donut holes.
USD15, 1 hour

10:30 AM

Visit Millennium Park

Marvel at the iconic Cloud Gate sculpture ('The Bean') and enjoy the beautiful gardens and public art installations.
Free, 2 hours

1:00 PM

Lunch at Portillo's

Savor Chicago-style hot dogs and Italian beef sandwiches at this famous eatery.
USD20, 1 hour

2:30 PM

Explore Navy Pier

Experience the vibrant atmosphere at Navy Pier with shops, eateries, and stunning views of Lake Michigan.
Free, 3 hours

6:00 PM

Dinner at Giordano's

Indulge in a delicious deep-dish pizza, a must-try when in Chicago.
USD30, 1.5 hours
Find Hotels in Chicago

Day 2: Chicago Sightseeing

Chicago, IL on March 17, 2025

8:00 AM

Breakfast at Wildberry Pancakes and Cafe

Enjoy a hearty breakfast with a variety of pancake options to energize you for the day.
USD15, 1 hour

9:30 AM

Visit the Art Institute of Chicago

Explore one of the oldest and largest art museums in the United States, home to valuable works by famous artists.
USD25, 2.5 hours

12:00 PM

Lunch at The Smith

Savor delicious American cuisine and a vibrant atmosphere at this popular bistro.
USD25, 1 hour

1:30 PM

Stroll down the Magnificent Mile

Enjoy a scenic walk along this historic shopping avenue filled with high-end shops and lovely architecture.
Free, 2 hours

4:00 PM

Visit the Willis Tower Skydeck

Take in breathtaking views of the city from the observation deck of one of the tallest buildings in the world.
USD30, 2 hours

6:30 PM

Dinner at The Girl & The Goat

Experience a unique dining option with great small plates inspired by global flavors.
USD50, 2 hours
Find Hotels in Chicago

Day 3: Exploring Culture

Chicago, IL on March 18, 2025

8:00 AM

Breakfast at Eggy's Diner

Start the day with a comfortable breakfast featuring their famous egg dishes.
USD15, 1 hour

9:30 AM

Visit the Field Museum

Explore fascinating exhibits including Sue, the most complete T. rex skeleton ever found.
USD25, 2.5 hours

12:00 PM

Lunch at Al's Beef

Taste the Chicago Italian beef sandwich that has become a local legend.
USD10, 1 hour

1:30 PM

Visit Shedd Aquarium

Discover a world of aquatic life at one of the largest and most visited aquariums in the world.
USD40, 3 hours

5:30 PM

Dinner at The Chop House

Enjoy a fine dining experience at one of Chicago’s premier steakhouses.
USD70, 2 hours
Find Hotels in Chicago

Day 4: Travel to Indianapolis

Indianapolis, IN on March 19, 2025

8:00 AM

Breakfast at Cafe Patachou

Grab a fresh breakfast with cottage style and local ingredients at this celebrated café.
USD15, 1 hour

10:00 AM

Drive to Indianapolis

Travel to Indianapolis, enjoying the scenic 3-hour drive.
USD0, 3 hours

1:00 PM

Lunch at St Elmo Steak House

Famous for its Shrimp Cocktail and classic steak dishes, a must-visit when in Indianapolis.
USD50, 1.5 hours

3:00 PM

Visit the Indianapolis Motor Speedway

Take a tour of the iconic motor speedway, home to the Indy 500 race.
USD20, 2 hours

6:00 PM

Dinner at Milktooth

Delight in a trendy twist on brunch favorites served in an eclectic setting.
USD25, 1.5 hours
Find Hotels in Indianapolis

Day 5: Indianapolis Attractions

Indianapolis, IN on March 20, 2025

8:00 AM

Breakfast at The Bagel Deli

Enjoy freshly made bagels with a variety of toppings to kick start your day.
USD10, 1 hour

9:30 AM

Visit the Indiana State Museum

Learn about Indiana’s history and culture through engaging exhibits.
USD15, 2 hours

12:00 PM

Lunch at Bluebeard

Enjoy seasonal dishes and craft cocktails in a cozy environment.
USD25, 1.5 hours

1:30 PM

Explore White River State Park

Relax and unwind at this urban park featuring beautiful landscapes.
Free, 2 hours

4:00 PM

Visit the Eiteljorg Museum

Discover the art and culture of the American West and Native Americans.
USD15, 1.5 hours

6:00 PM

Dinner at The Eagle

Dine at a Southern-inspired restaurant with a focus on fried chicken and comfort food.
USD20, 2 hours
Find Hotels in Indianapolis
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your Trip to Chicago, Illinois, Indianna for Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go