The Ultimate City Road Trip from New York City to Chicago

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  • New York City, NY
  • Philadelphia, PA
  • Pittsburg, PA
  • Cleveland, OH
  • Chicago, IL
  • Best time
  • Roadside assistance
  • Cheap car insurance
Though only hours away, the cities of the Northeast and Midwest feel worlds apart because of their unique attitudes and cultures. This road trip takes you through some of the highlights, traveling from New York through Pennsylvania, and Ohio before ending up in Chicago, Illinois.
It can be time-consuming to plan the best road trip, but the car insurance comparison and broker app Jerry has you covered with everything you need for the ultimate road trip from NY to Chicago.
But before you head out, be sure you have great car insurance and roadside assistance. Nothing kills a good road trip vibe faster than a flat, but Jerry’s roadside assistance program will have you back on track in no time! Ready to hit the road? Let’s get started in New York, New York.
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Start in New York City

In the city that never sleeps, it is easy to get overwhelmed with things to do, sights to see, and food to eat. You’ll want to plan a few days in the Big Apple before you set out on your journey.

Where to stay

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. Staying here, it’s easy to get to most parts of the city.
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 and is just blocks away from some of the best shopping and dining in the city.

Where to eat

Prominently featured in the classic film When Harry Met Sally, Katz’s Delicatessen 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.
We’d be remiss to not include a pizza place on our list of NYC restaurants. Famous Joe’s Pizza is as classic as it gets. Come here for a cheap slice of greasy, cheesy goodness.

What to do

If you’re a museum lover, the Metropolitan Museum of Art has world-famous art exhibits, ranging from Egyptian art to impressionism. For a non-art museum, the sobering 9/11 Memorial and Museum should not be missed.
New York is also known for its top-notch performances. You can get last-minute tickets to a Broadway show at a TKTS stand or check out the legendary Studio 54 for cabaret-style performances.
Outdoor enthusiasts should take a walk along the High Line, an elevated freight railway turned park in Chelsea. While you’re there, check out Chelsea Piers for a chance to hit golf balls along the Hudson River.
Wooden posts stick out of the water at Chelsea Piers, New York City. The sunset reflects an orange glow.
Chelsea Piers, New York City, New York

New York to Philadelphia

95 miles, 1.5 hours
Leave the hustle and bustle of New York City for its smaller neighbor. Philadelphia is the birthplace of the American Constitution and is brimming with history. Aside from the landmarks of American history, Philadelphia has a top-notch art and culinary scene.

Where to eat

If there’s one food that’s synonymous with Philadelphia, it has to be the cheesesteak—and nothing beats Jim’s South Street. 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 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 in Philadelphia

Start by visiting 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.
There are plenty of Instagrammable spots in Philadelphia. Head over to the LOVE Park to take a picture with the famous sign or climb the steps of the Philadelphia Museum of Art to take a selfie with the Rocky statue. For a truly unique outdoor art experience, go on a tour of public art with Mural Arts Philadelphia.
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A horse-drawn carriage carries tourists past the brick facade of Independence Hall, Philadelphia.
Independence Hall, Philadelphia, Pennsylvania

Philadelphia to Pittsburgh

305 miles, 5 hours
The route from Philadelphia to Pittsburgh takes you through the heart of Pennsylvania. With an industrial background, the City of Brotherly Love is one of artistic and scientific excellence.

Where to stay

About 7 hours into your drive, Pittsburgh is a great place to stay for the night. We recommend the Pittsburgh Marriott City Center for a conveniently located hotel at an affordable price.

Where to eat

Pittsburgh restauranteurs Denise Josephs and Marlene Siddo opened up 2 Sisters 2 Sons with their sons. This takeout-only spot 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.
The Primanti Bros website proudly boasts that they’re the World Sandwich Headquarters—and we can’t say they’re wrong. Primanti Bros 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

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 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.
To stretch your legs, spend time at the Phipps Conservatory and Botanical Gardens, 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.
A mural featuring caricatures of famous Pennsylvania figures in Primanti Bros, Pittsburgh.
Primanti Bros, Pittsburgh, Pennsylvania

Pittsburgh to Cleveland

135 miles, 2.5 hours
Located between river banks and the southern shore of Lake Erie, Cleveland has been a manufacturing hub in the Midwest for many years. The city also has a vibrant cultural scene with world-class art institutions.

Where to eat

Larder is another deli—but with a focus on foraging, fermentation, and fresh ingredients, Larder is in a category of its own. When it opened in 2015, 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.
Inspired by the taco stands in Los Angeles, Hola serves some great tacos. 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

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.
If you’re looking for some quirky sites, Cleveland’s Super Electric Pinball Parlor and the A Christmas Story House and Museum are fun for the whole family.
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The white-tiled Rock and Roll Hall of Fame building stands near the water in Cleveland, Ohio.
Rock and Roll Hall of Fame, Cleveland, Ohio

Cleveland to Chicago

344 miles, 5.5 hours
Your last stop is the Windy City. Chicago is the biggest city in the Midwest and is known for its skyline full of skyscrapers, baseball, comedy, and hot dogs. As in New York, you can spend weeks experiencing all that Chicago has to offer.

Where to stay

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.
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 great value.

Where to eat

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.
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

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”!
For the best high-end shopping head to The Magnificent Mile. Take a walk through the Navy Pier for some family-friendly entertainment.
Chicago has plenty of options for nighttime activities, too. If you’re a baseball buff, take a trip to Wrigley Field and cheer on the Cubs. 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 Cloud Gate sculpture reflects Chicago buildings in Millennium Park on a sunny day.
Millennium Park, Chicago, Illinois

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

Both the Northeast and Midwest are known for extreme weather. To avoid getting stuck in winter storms and to beat the heat and humidity of summer, plan a road trip from NY to Chicago in the late spring or early summer.

Why you need roadside assistance

No matter what time of year you drive, you need a top-notch roadside assistance program.
Emergency roadside assistance from Jerry gives you access to fuel delivery, tire services, up to 10 miles of towing, and more—all at the touch of a button and for just $6.99.

Finding cheap car insurance

If you’re embarking on a road trip, you’ll also need a good car insurance policy. And there’s no easier way to get it than with Jerry.
It’s this simple: download the Jerry app and answer a few simple questions. In less than 45 seconds, Jerry collects all of your information from your existing insurer and presents you with competitive quotes from up to 50 top insurance companies.
Choose the policy that fits your needs and Jerry takes care of everything else, from securing your new policy and canceling your old one. No long forms, no calling around, no hard work—just savings. The average Jerry user saves $879 per year on car insurance!
Jerry blew my mind, honestly. It took me 10 minutes and I ended up with $100 of savings a month. Best of all, customer service answered all my questions about rental car reimbursement and roadside assistance.” ––Savanna R.
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