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Ultimate Road Trip from Charlotte to Chicago with 3 Days of Adventure

Viewed by 115 travelers

Day 1: Charlotte to Dayton

Dayton, OH on March 25, 2025

8:00AM

Breakfast at Snooze, an A.M. Eatery

Start your road trip with a hearty breakfast at Snooze, famous for its inventive pancakes and delicious egg dishes.
USD20, 1 hour

9:30AM

Depart from Charlotte

Set off on your 8-hour drive to Dayton, enjoying scenic views along I-77 and I-70.
USD0, 8 hours

5:30PM

Check-in at Courtyard by Marriott Dayton

Relax and refresh at this conveniently located hotel for a restful night.
USD120, 1 hour

7:00PM

Dinner at The Nite Owl

Savor contemporary comfort food at The Nite Owl, known for its unique spin on classic dishes.
USD30, 1.5 hours
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Day 2: Dayton to Chicago

Chicago, IL on March 26, 2025

8:00AM

Breakfast at First Watch

Enjoy a nutritious breakfast with fresh ingredients at First Watch, a local favorite.
USD15, 1 hour

9:30AM

Depart from Dayton

Hit the road for your 3-hour journey to the Windy City, Chicago!
USD0, 3 hours

12:30PM

Check-in at Hotel Chicago Downtown

Settle into your hotel, perfectly situated to explore Chicago’s top attractions.
USD200, 1 hour

1:30PM

Lunch at Portillo's

Grab a Chicago-style hot dog and Italian beef sandwich at Portillo's, a must-try local eatery.
USD15, 1 hour

3:00PM

Visit Millennium Park

Explore this iconic park and take pictures with the famous Cloud Gate (The Bean). Don't miss the beautiful gardens.
USD0, 2 hours

5:00PM

Visit Art Institute of Chicago

Discover an incredible collection of art from ancient to modern times at this world-renowned museum.
USD25, 2 hours

7:30PM

Dinner at Lou Malnati's Pizzeria

Enjoy Chicago’s iconic deep-dish pizza at Lou Malnati's, a beloved local institution.
USD25, 1.5 hours
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Day 3: Full Day in Chicago

Chicago, IL on March 27, 2025

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with gourmet pancakes and creative brunch items at Wildberry Pancakes.
USD20, 1 hour

9:30AM

Visit Willis Tower Skydeck

Get breathtaking views of Chicago from the Skydeck, with its glass ledge extending out over the city.
USD30, 1.5 hours

11:00AM

Exploring Riverwalk

Stroll along the picturesque Riverwalk, where you can take in stunning architecture and local art.
USD0, 2 hours

1:00PM

Lunch at Shake Shack

Enjoy delicious burgers and milkshakes at Shake Shack, a not-to-miss fast-casual chain.
USD15, 1 hour

2:30PM

Visit Field Museum

Explore the vast collections at the Field Museum, including the famous Sue the T. rex.
USD30, 3 hours

5:30PM

Shopping at Magnificent Mile

Indulge in an afternoon of shopping on the Magnificent Mile, with everything from boutiques to department stores.
USD0, 2.5 hours

8:00PM

Dinner at The Capital Grille

Finish your trip with a fine dining experience at The Capital Grille, known for its dry-aged steaks and exquisite wine selection.
USD60, 2 hours
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