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Epic Road Trip: New York to Chicago in 7 Days

Viewed by 456 travelers

Day 1: Explore NYC

New York City, USA

8:00AM

Breakfast at Ess-a-Bagel

Start your trip with a mouth-watering New York bagel with cream cheese and lox from the iconic Ess-a-Bagel.
Walk to the subway station for easy access to the city.
AUD 15, 1 hour

9:30AM

Visit Central Park

Stroll through Central Park, taking in the scenic views and iconic spots like Bethesda Terrace.
Easily accessible by walking from Ess-a-Bagel.
Free, 2 hours

12:00PM

Lunch at Shake Shack

Indulge in a classic burger and fries at Shake Shack before heading out of the city.
Take a short Uber ride to Shake Shack in Madison Square Park.
AUD 20, 1 hour

1:30PM

Hit the Road to Philadelphia

Begin your drive to Philadelphia, enjoying the scenic route along the way.
Drive via I-95 S, approximately 1.5 hours to Philadelphia.
AUD 50 (fuel), 1.5 hours
Find Hotels in New York City

Day 2: Philly Adventures

Philadelphia, USA

8:00AM

Breakfast at Café La Maude

Enjoy a delightful brunch with French and Lebanese flair at this charming cafe.
Located in Northern Liberties, a short drive from your accommodation.
AUD 25, 1 hour

9:30AM

Explore the Liberty Bell

Visit the historic Liberty Bell and Independence Hall, two essential Philadelphia landmarks.
Short drive or a quick walk from the café.
Free, 1.5 hours

11:30AM

Lunch at Reading Terminal Market

Sample local delicacies and a cheesesteak at this bustling market with various food options.
Short drive to the market.
AUD 15, 1.5 hours

1:00PM

Head to Washington D.C.

Take a scenic drive to our nation’s capital, Washington D.C.
Drive via I-95 S, approximately 2 hours.
AUD 50 (fuel), 2 hours
Find Hotels in Philadelphia

Day 3: D.C. Connections

Washington D.C., USA

8:00AM

Breakfast at Founding Farmers

Fuel up with farm-to-table breakfast options at this popular spot.
Short drive or ride-share to the restaurant.
AUD 20, 1 hour

9:30AM

National Mall Exploration

Spend the morning wandering the National Mall, taking in the Lincoln Memorial and the Washington Monument.
Walking distance from Founding Farmers.
Free, 2.5 hours

12:00PM

Lunch at Old Ebbitt Grill

Treat yourself to an iconic D.C. meal at this historic restaurant near the White House.
Short walk from the National Mall.
AUD 30, 1 hour

1:30PM

Drive to Pittsburgh

Continue your journey to Pittsburgh, known for its steel bridges and beautiful hills.
Drive via I-76 W, approximately 3 hours.
AUD 50 (fuel), 3 hours
Find Hotels in Washington D.C.

Day 4: Steel City Fun

Pittsburgh, USA

8:00AM

Breakfast at Pamela's Diner

Enjoy a famous breakfast at Pamela's, known for their pancakes and unique charm.
Located in the Strip District, a short drive from your hotel.
AUD 20, 1 hour

9:30AM

Visit the Point State Park

Take in panoramic views of the confluence of rivers at this beautiful park in Pittsburgh.
Short drive from the diner.
Free, 1.5 hours

11:30AM

Lunch at Primanti Bros.

Experience Pittsburgh's famous sandwich loaded with fries and coleslaw in the sandwich.
Quick drive to the restaurant.
AUD 15, 1 hour

1:00PM

Head to Columbus

Leave Pittsburgh en route to Columbus, Ohio.
Drive via I-70 W, approximately 3 hours.
AUD 50 (fuel), 3 hours
Find Hotels in Pittsburgh

Day 5: Columbus Attractions

Columbus, USA

8:00AM

Breakfast at Katalina's

Savour a delicious breakfast taco or French toast at this local hot spot.
Easy drive to the downtown location.
AUD 15, 1 hour

9:30AM

Explore the Franklin Park Conservatory

See beautiful gardens and stunning art exhibits at this botanical treasure.
Short drive from the café.
AUD 20, 2 hours

12:00PM

Lunch at North Market

Experience a range of culinary delights from local vendors at this vibrant market.
Short drive to North Market.
AUD 25, 1.5 hours

1:30PM

Drive to Indianapolis

Continue your road trip towards Indianapolis, Indiana.
Drive via I-70 W, approximately 2 hours.
AUD 40 (fuel), 2 hours
Find Hotels in Columbus

Day 6: Indy Highlights

Indianapolis, USA

8:00AM

Breakfast at Milktooth

Delight in a trendy brunch with standout dishes crafted by local chefs.
Located in the Fletcher Place neighborhood, easy to reach.
AUD 25, 1 hour

9:30AM

Visit the Indianapolis Motor Speedway

Tour the world-famous speedway and the interactive Hall of Fame Museum.
Short drive from the café.
AUD 20, 2 hours

12:00PM

Lunch at St. Elmo Steak House

Experience the classics at one of Indianapolis' most legendary steakhouses.
Drive to St. Elmo's in downtown Indianapolis.
AUD 60, 1.5 hours

2:00PM

Drive to Chicago

Conclude your road trip with the final leg to Chicago, Illinois.
Drive via I-65 N, approximately 3 hours.
AUD 50 (fuel), 3 hours
Find Hotels in Indianapolis

Day 7: Discover Chicago

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Start your Chicago adventure with breakfast at this iconic diner known for its generous portions.
Located in the West Loop, a short drive from downtown.
AUD 20, 1 hour

9:30AM

Explore Millennium Park

Take a stroll in Millennium Park to see The Bean and enjoy the stunning art installations.
Short drive or ride-sharing to the park.
Free, 2 hours

12:00PM

Lunch at Portillo's

Indulge in an authentic Chicago-style hot dog for lunch at this famous eatery.
A quick drive to the nearest location.
AUD 15, 1 hour

1:30PM

Visit the Art Institute of Chicago

Spend the afternoon exploring the world-class collection at this iconic art museum.
Short drive from Portillo's.
AUD 25, 2.5 hours

4:00PM

Itinerary Wrap-up

Reflect on your incredible journey and plan your next adventure from the windy city.
Return to your accommodations or explore nearby activities.
Free, Varies
Find Hotels in Chicago
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