The Ultimate City Road Trip from New York City to Chicago

Key trip details

Itinerary

New York City, NY— 2 to 3 days
Philadelphia, PA—1 to 2 days
Pittsburgh, PA—One half to 2 days
Cleveland, OH—One half to 2 days
Chicago, IL—2 to 3 days

Start in New York City

Where to stay

Archer Hotel
: Near Midtown—but away from the chaos of Times Square—the Archer Hotel is trendy and offers some of the best views of the Empire State Building. It's easy to get around the city from this location. Cost per night: from $251
James New York
: If Downtown is more your vibe, check out the James New York in SoHo. It’s right in the heart of the hip downtown neighborhood, is just blocks away from some of the best shopping and dining in the city. Cost per night: from $300

Where to eat

Katz's Deli
($$-$$$): Prominently featured in the classic film When Harry Met Sally, Katz’s Delicatessen, located in the Lower East Side, has been serving some of the best pastrami and corned beef since 1888. In addition to their sky-high sandwiches, they serve typical deli food including knishes, bagels, and matzo ball soup.
Famous Joe's Pizza
($): We’d be remiss to not include a pizza place on our list of NYC restaurants. The Greenwich Village institution, Famous Joe’s Pizza, is as classic as it gets. Come here for a cheap slice of greasy, cheesy goodness.
Juniors
($$-$$$): If you're hanging around Midtown after seeing a Broadway show, Juniors is the place to get a slice of classic New York Cheesecake. The menu is extensive—with deli and diner classics—but the dense, creamy cheesecakes topped with strawberry sauce are what put this restaurant on the map.

What to do

The Metropolitan Museum of Art
($$): The Met is one of the leading art institutions in the world. You can easily spend several days roaming the halls of the museum, which is located on 5th Avenue along the eastern edge of Central Park. We recommend you start with the Egyptian art, but the impressionist galleries are also not to be missed.
The 9/11 Memorial & Museum
($$): The 9/11 Memorial and Museum, located at the site of the original Twin Towers, is a sobering tribute to the lives lost and the heroes of September 11, 2001. The museum beautifully tells stories of those who experienced the events of 9/11 first-hand while also examining the impact of that fateful day.
Broadway Shows and
TKTS
tickets ($$-$$$$): Broadway is the beating heart of New York City. Score a seat to a hot-ticket show, like Hamilton or Wicket, or try your luck with the TKTS booth—located in Times Square—to get a day-of ticket to some top-quality entertainment.
The High Line
(Free): For those who want to spend some time outdoors in the big city, take a walk along the High Line, an elevated freight railway turned park in Chelsea. It sits above the Chelsea Market so you can grab a bite or get some shopping done while you're there.
Chelsea Piers
($$-$$$): After The High Line, check out Chelsea Piers for a chance to hit golf balls along the Hudson River. The recreational center has a driving range, climbing wall, ice rink, and more—fun for the whole family!

New York to Philadelphia

Where to stay

Kimpton Hotel Monaco Philadelphia
: With a prime location right near Independence Historic Park the Kimpton Hotel Monaco is a great place to spend the night. Cost per night: from $200

Where to eat

Sabrina's Cafe - Art Museum
($$): A perfect place for breakfast as you arrive in Philadelphia before heading to the nearby art museum, Sabrina's has a menu complete with breakfast classics and local specialties. For a truly decadent meal, try the Cannoli French Toast—if savory is more you're thing, locals love the Shrimp and Grits.
Jim's South Street
($): If there’s one food that’s synonymous with Philadelphia, it has to be the cheesesteak—and nothing beats Jim’s South Street—conveniently situated just down the street from the Liberty Bell. You can stick with classic meat, cheese, peppers, and onions, or you can ask for a sandwich "whiz wit" for a hoagie with cheese whiz and fried onions.
Zahav
($$$): For those staying overnight in Philadelphia, Zahav is the place to go for a nice meal. The Israeli restaurant helped put the Philly food scene on the map. Guests are treated to a fixed menu featuring the restaurant’s famous hummus and Chef Michael Solomonov’s signature lamb shoulder. You’ll need to book this one in advance. Reservations are released 60 days in advance and they go fast.

What to do

Independence National Historic Park
: America’s only UNESCO World Heritage Site. Book a free ticket to tour Independence Hall, then swing by the Liberty Bell to get a peek at a symbol of American history. Other sites in the park include Carpenter’s Hall and the Benjamin Franklin Museum. Budget 30 minutes for each location.
Philadelphia Museum of Art
($$): A world-class museum, the Philadelphia Museum of Art houses pieces from master artists such as Mary Cassatt, Frank Gehry, and Rembrandt, among others. As you climb up the steps to the museum, be sure to take a picture with the famous Rocky statue.

Philadelphia to Pittsburgh

Where to stay

Pittsburgh Marriott City Center
: Conveniently located in the middle of the city, the Pittsburgh Marriott City Center is a comfortable place to stay at an affordable price. Cost per night: from $330 a night

Where to eat

2 Sisters 2 Sons
($$-$$$): Pittsburgh restauranteurs Denise Josephs and Marlene Siddo opened up 2 Sisters 2 Sons with their sons. This takeout-only spot near the Allegheny River serves authentic Caribbean and Jamaican dishes like jerk chicken, whole red snapper, oxtail, and sweet plantains. The dishes are affordable with big portions, and you won’t find many of them anywhere else in Pittsburgh.
Primanti Bros
($-$$): The Primanti Bros website proudly boasts that they’re the World Sandwich Headquarters—and we can’t say they’re wrong. The Primanti Bros chain was founded in Pittsburgh in 1933 and has been serving sky-high sandwiches ever since. While sandwiches are what they are known for, the wings, with a choice of 11 sauces, are not to be missed.

What to do

The Carnegie Museums
($$): The Carnegie Museum isn't just one museum, but four museums—with something bound to entertain the entire family. Visit the Carnegie Museum of Natural History, Carnegie Museum of Science, or the Carnegie Museum of Art to get a glimpse into the history of the early 20th-century industrial capital.
The Andy Warhol Museum
($$): The fourth museum in the Carnegie Museum family is dedicated to another son of Pittsburgh. The Andy Warhol Museum has the largest collection of Warhol’s work and archival materials.
Phipps Conservatory and Botanical Gardens
($$): Visit one of America’s oldest conservatories. Take a day wandering through the gardens and visit the 14-room greenhouse, featuring industry-leading sustainable technologies and green practices.

Pittsburgh to Cleveland

Where to stay

Westin Cleveland Downtown
: In the center of Downtown Cleveland, the Westin has great views and an even better location. With suite-style rooms available, it's a comfortable family stop. Cost per night: from $179

Where to eat

Larder
($$-$$$): With a focus on foraging, fermentation, and fresh ingredients, Larder is a deli in a category of its own. The team made it a goal to only source ingredients from local Ohio vendors and farmers—as a result, Larder has an innovative menu that changes seasonally. It's conveniently located just five minutes from the Rock and Roll Hall of Fame.
Hola
($-$$): Inspired by the taco stands in Los Angeles, Hola serves some great tacos—in three locations throughout Cleveland. The famous birria tacos put them on the map with their perfectly braised beef and salty consomme dipping sauce. Their fusion dishes—birria pizza and Mexican ramen—wonderfully blend cuisines for a truly unique food experience. For a refreshing end to your meal, try a homemade paleta (Mexican ice pop).

What to do

Rock and Roll Hall of Fame
($$): *Perhaps the most well-known museum in Cleveland, the Rock and Roll Hall of Fame chronicles the history of rock and roll in seven stories of exhibits. Budget half a day to visit Rock Hall to see all of the highlights, including rotating exhibits, memorabilia, and the hall of fame itself.
Christmas Story House
($$): Located just south of Downtown, movie buffs can take a tour of Ralphie's house in the Christmas Story House and Museum. The house has memorabilia from the movie—including the famous leg lamp. For die-hard fans, there is even the option to stay the night!

Cleveland to Chicago

Where to stay

Sofitel Chicago
: Conveniently situated on the Magnificent Mile, the Sofitel Chicago is a warm and welcoming hotel. The diverse clientele adds to the cosmopolitan atmosphere and the buzzy hotel bar is great to come home to after a long day on the town. Cost per night: from $287
Hotel Lincoln
: Hotel Lincoln is located in the trendy neighborhood of Lincoln Park and is close to attractions like the Lincoln Park Zoo. With views of Lake Michigan, this hotel is a prime location for a great value. Cost per night: from $141

Where to eat

Pequod's Pizza
($$):* While you may hear the classic battle between Lou Malnati’s and Giordano’s, we think the real deep dish champion is Pequod’s in Lincoln Park. Known for its caramelized crust, this cheesy, tomato-y pie is one of the best in the city. Depending on your preference, add meat for a carnivore’s delight or top with veggies and pretend it’s a salad.
Greek Islands
($$): Chicago’s Greektown is one of the best neighborhoods for food in the country, let alone the city, and Greek Islands is a local hotspot. Start your meal with the flaming saganaki, a flambéed cheese specialty, before diving into the many Mediterranean options. We recommend the moussaka, leg of lamb, or chicken souvlaki for a traditional meal.

What to do

Millenium Park
(Free): No trip to Chicago is complete without a stop at Millennium Park. Situated right above The Art Institute of Chicago—another Chicago must-see—Millennium Park has incredible art, architecture, and landscaping. Don’t forget to snap your picture in "The Bean"!
The Magnificent Mile
: For the best high-end shopping in the city, take a spin on Miracle Mile. The stretch of shops in the Michigan Avenue District has some of the best restaurants and stores in the city.
See a
Cubs
game ($$$): If you're passing through Chicago in the summer, there is no better way to spend an evening than with a Chicago Dog at Wrigley Field.
Have some laughs at
The Second City
($$): Chicago is home to some of the country’s top comedy groups, so be sure to see a show at The Second City, where many SNL favorites got their start.

The best time of year to drive from New York City to Chicago

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