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Family-Friendly City Road Trip: Chicago to New York and Back

Viewed by 164 travelers

Day 1: Chicago Exploration

Chicago, IL, USA

8:00AM

Breakfast at Lou Mitchell's

Start your day with a hearty breakfast at Lou Mitchell's, a classic diner known for its delicious pancakes and omelets.
Lou Mitchell's is located in the West Loop area of Chicago, about a 15-minute drive from downtown.
$, 1 hour

10:00AM

Millennium Park

Visit Millennium Park to see the famous Cloud Gate sculpture, also known as 'The Bean', and enjoy a leisurely stroll around the park.
Millennium Park is located in the Loop area of Chicago, a short walk from Lou Mitchell's.
Free, 2 hours

1:00PM

Lunch at Portillo's

Grab lunch at Portillo's and try their iconic Chicago-style hot dogs and Italian beef sandwiches.
Portillo's is a 20-minute drive from Millennium Park, located in the River North neighborhood.
$, 1 hour

3:00PM

Shedd Aquarium

Explore the Shedd Aquarium to see a variety of marine life, including dolphins, sharks, and jellyfish.
The Shedd Aquarium is located by Lake Michigan, a 15-minute drive from Portillo's.
$$, 2 hours

6:00PM

Dinner at Giordano's

End your day with a deep-dish pizza dinner at Giordano's, a famous Chicago pizzeria.
Giordano's is a 15-minute drive from the Shedd Aquarium, located in the South Loop area.
$$, 1.5 hours
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Day 2: Family Fun in Cleveland

Cleveland, OH, USA

8:00AM

Breakfast at West Side Market

Start your day with breakfast at West Side Market, a historic market with various food vendors offering delicious options.
West Side Market is located in Ohio City, a 15-minute drive from downtown Cleveland.
$, 1.5 hours

10:00AM

Rock and Roll Hall of Fame

Visit the Rock and Roll Hall of Fame to explore the history of rock music and see iconic memorabilia.
The Rock and Roll Hall of Fame is located by Lake Erie, a short drive from West Side Market.
$$, 2.5 hours

1:00PM

Lunch at Sokolowski's University Inn

Enjoy a traditional Polish lunch at Sokolowski's University Inn, a Cleveland institution known for its pierogies and schnitzel.
Sokolowski's University Inn is a 10-minute drive from the Rock and Roll Hall of Fame.
$, 1 hour

3:00PM

Cleveland Metroparks Zoo

Spend the afternoon at the Cleveland Metroparks Zoo, home to a wide variety of animals and educational exhibits.
The Cleveland Metroparks Zoo is a 20-minute drive from Sokolowski's University Inn.
$$, 2 hours

6:00PM

Dinner at Mabel's BBQ

Enjoy a dinner of delicious barbecue ribs and brisket at Mabel's BBQ, a popular spot in Cleveland.
Mabel's BBQ is located in the downtown area, a 15-minute drive from the zoo.
$$, 1.5 hours
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Day 3: Pittsburgh Charm

Pittsburgh, PA, USA

8:00AM

Breakfast at Pamela's Diner

Start your day with a delicious breakfast at Pamela's Diner, known for its famous crepe-style pancakes.
Pamela's Diner is located in the Strip District, a 10-minute drive from downtown Pittsburgh.
$, 1 hour

10:00AM

Duquesne Incline

Ride the Duquesne Incline for panoramic views of Pittsburgh and the three rivers that converge in the city.
The Duquesne Incline is a short drive from Pamela's Diner, located on Mount Washington.
$, 1.5 hours

12:00PM

Lunch at Primanti Bros

Try the famous sandwiches at Primanti Bros, a Pittsburgh institution known for putting fries and coleslaw on their sandwiches.
Primanti Bros has multiple locations in Pittsburgh, with the original in the Strip District.
$, 1 hour

2:00PM

Phipps Conservatory and Botanical Gardens

Explore the beautiful Phipps Conservatory and Botanical Gardens, featuring a variety of plant species and seasonal flower displays.
Phipps Conservatory is located in Schenley Park, a short drive from Primanti Bros.
$$, 2 hours

5:00PM

Dinner at Meat & Potatoes

Enjoy a farm-to-table dining experience at Meat & Potatoes, known for its creative dishes and cozy atmosphere.
Meat & Potatoes is located in the Cultural District, a 15-minute drive from Phipps Conservatory.
$$, 1.5 hours
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Day 4: Historic Philadelphia

Philadelphia, PA, USA

8:00AM

Breakfast at Reading Terminal Market

Start your day with breakfast at Reading Terminal Market, a bustling food hall with a wide variety of vendors offering delicious options.
Reading Terminal Market is located in Center City, Philadelphia, a short drive from downtown.
$, 1.5 hours

10:00AM

Independence National Historical Park

Explore Independence National Historical Park, home to iconic landmarks such as the Liberty Bell and Independence Hall.
The park is within walking distance from Reading Terminal Market.
$, 2 hours

1:00PM

Lunch at Pat's King of Steaks

Try a classic Philly cheesesteak for lunch at Pat's King of Steaks, a renowned spot for this iconic sandwich.
Pat's King of Steaks is a 15-minute drive from Independence National Historical Park.
$, 1 hour

3:00PM

Philadelphia Zoo

Visit the Philadelphia Zoo, America's first zoo, and explore its diverse animal exhibits and interactive experiences.
The Philadelphia Zoo is located in Fairmount Park, a 20-minute drive from Pat's King of Steaks.
$$, 2 hours

6:00PM

Dinner at Zahav

Indulge in modern Israeli cuisine at Zahav, a critically acclaimed restaurant in Philadelphia.
Zahav is located in Society Hill, a 15-minute drive from the Philadelphia Zoo.
$$$, 1.5 hours
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Day 5: New York City Adventure

New York City, NY, USA

8:00AM

Breakfast at Sarabeth's

Start your day with a delicious breakfast at Sarabeth's, known for its iconic brunch dishes and baked goods.
Sarabeth's has multiple locations in NYC, with the flagship in Tribeca.
$$, 1.5 hours

10:00AM

Central Park

Explore Central Park, a sprawling green oasis in the heart of Manhattan, with various attractions and beautiful landscapes.
Central Park is easily accessible by foot or public transportation from Sarabeth's.
Free, 2 hours

1:00PM

Lunch at Katz's Delicatessen

Enjoy a classic deli lunch at Katz's Delicatessen, famous for its pastrami sandwiches and kosher pickles.
Katz's Delicatessen is located on the Lower East Side, a short subway ride from Central Park.
$, 1 hour

3:00PM

The Metropolitan Museum of Art

Visit The Met, one of the world's largest and most prestigious art museums, housing a vast collection of art spanning centuries.
The Metropolitan Museum of Art is located on the Upper East Side, a quick subway ride from Katz's Delicatessen.
$$, 2.5 hours

6:00PM

Dinner at Junior's Restaurant

End your day with a delicious dinner at Junior's Restaurant, known for its famous cheesecake and classic American dishes.
Junior's Restaurant has multiple locations in NYC, with the original in Brooklyn.
$$, 1.5 hours
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Day 6: Washington D.C. Exploration

Washington D.C., USA

8:00AM

Breakfast at Founding Farmers

Start your day with a farm-to-table breakfast at Founding Farmers, known for its sustainable and delicious dishes.
Founding Farmers has multiple locations in the D.C. area, with one near the White House.
$$, 1.5 hours

10:00AM

National Mall and Monuments

Explore the National Mall and visit iconic monuments and memorials such as the Lincoln Memorial and Washington Monument.
The National Mall is a walking distance from Founding Farmers, with various sites to see.
Free, 2 hours

1:00PM

Lunch at Ben's Chili Bowl

Try a famous half-smoke chili dog at Ben's Chili Bowl, a historic eatery in D.C. loved by locals and visitors alike.
Ben's Chili Bowl is located in the U Street Corridor, a short drive or metro ride from the National Mall.
$, 1 hour

3:00PM

Smithsonian National Air and Space Museum

Visit the Smithsonian National Air and Space Museum to learn about aviation history and space exploration.
The museum is located on the National Mall, close to other monuments and memorials.
$, 2 hours

6:00PM

Dinner at Old Ebbitt Grill

Enjoy dinner at Old Ebbitt Grill, a historic restaurant near the White House known for its classic American dishes.
Old Ebbitt Grill is a short walk from the Smithsonian National Air and Space Museum.
$$$, 2 hours
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