The Best Road Trip from Chicago to Maine
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- Chicago to Cleveland
- Cleveland to Niagara Falls
- Niagara to NYC
- New York to Boston
- Boston to Acadia National Park
- Acadia National Park
- Roadside assistance
- Quick route
- Scenic route
- Cheap insurance
Start in Chi-Town before winding through some of the northeast’s best spots and finishing your journey in stunning Acadia National Park.
A Chicago to Maine road trip isn’t necessarily the first route that comes to mind for a summer road trip—but it’s a fascinating one. Exploring industrial cities and natural splendor, the nearly 1,500-mile drive is essential for those up for something a little different.
On the way, you’ll stop in New York and Boston and find iconic spots in Chicago and Cleveland. And at the end of it all, you’re rewarded with magnificent views of the Atlantic.
To help you enjoy the perfect road trip, car insurance comparison and broker app Jerry has assembled an eight-day itinerary, including the best food, hotels, and activities in each spot.
But before you hit the road, make sure you have roadside assistance and car insurance! Nothing ruins a trip quite like a busted battery or unfortunate collision, and Jerry has all that sorted. Jerry’s roadside assistance program starts at just $6.99 for one vehicle and will give you peace of mind as you meander through the northeast.
Start in Chicago
You’d be remiss to leave Chicago without seeing some of its iconic attractions.
For day one of your trip, enjoy some of the city’s best food, culture, and sport. We’ve assembled some of the essentials, but if you see a cool restaurant or fun activity, go for it! There is, quite literally, too much to do in a day.
Eat breakfast at Batter and Berries. The unassuming streetside spot is famous for its rotating recipes for french toast, so you’ll always have something different to try!
Grab a quick lunch at Nhu Lan bakery for banh mi. Their affordable sandwiches are some of the best around!
Change things up with a pub dinner at Pleasant House. A loose interpretation of a British gastropub, their steak and ale pies served with chunky chips make for a hearty dinner.
Stroll around the Field Museum in the morning. It’s an iconic Chicago cultural experience and one of the best natural history museums in the world.
In the afternoon, dip into the Art Institute of Chicago, a fine museum that now has the portraits of Barack and Michelle Obama adorning its walls.
To finish off your cultural experience, take in a Chicago Cubs game at Wrigley Field. It’s the second-oldest venue in Major League Baseball and well worth the trip for the ambiance and hot dogs alone!
Bed in for the night at emc2 Chicago, a trendy hotel in the middle of the famous Magnificent Mile.
Chicago to Cleveland
Journey time: 6 hours including stops
Hit the road for the first time, sauntering out of one famous midwestern city and into another—with a bit of outdoor fun mixed in!
Go for breakfast at M. Henry in Chicago. Their drunken eggs are a hit, but if you want to get going quickly, they also offer carry-out pastries and coffee. Grab something for lunch, too, since you’re in for a bit of a drive to Cleveland.
There are loads of good restaurants in Cleveland. One of the best is Momocho, a Mexican cantina with a nice outdoor patio.
On your way to Cleveland, take a detour to Indiana Dunes National Park. The 15-mile stretch along the shore of Lake Michigan is a good respite on the journey east. It may be a bit of a shock to see a beach in landlocked Indiana, but that’s part of the fun!
Once you get to Cleveland, relax for a bit at the Glidden House Hotel your home for the night. It’s listed in the national register of historic places and is ideally located near museums and some shopping.
Sleep at Glidden House for a blend of modern comfort and progressive-era architecture.
Cleveland to Niagara Falls
Journey time: 3 hours
Hit Cleveland’s defining museum—and an American cultural essential—before heading north towards the Canadian border. You certainly won’t be bored on a day when urban and country life clash.
You’ll want to make the most out of your day’s activities, so go for a quick breakfast at Luna Cafe—their crepes are yummy!
For lunch, look no further than Mabel’s BBQ, a hotspot on the Cleveland food scene that serves up fantastic mac n cheese to go with smoked meats.
Food options in Niagara Falls are plentiful, but for a more interesting experience check out Griffon gastropub. Their Aukra salmon served on top of ginger rice is a hit.
Visit the Rock & Roll Hall of Fame in the morning—and inevitably argue about the inclusion, or, perhaps, exclusion of some artists. Admission is $26 for adults.
After lunch, hit the road for an interesting three-hour drive to Niagara Falls. If you time it right and the weather is good, you’ll arrive at the iconic spot in the early evening. Stroll around, take some fantastic pictures, and enjoy the scenery.
Spend your night at The Giacomo, a comfy, art deco-style hotel close to Niagara Falls.
Niagara to NYC
Journey time: 6 hours
For the longest day of travel on the trip, head down New York State towards the Big Apple. Traffic permitting, you’ll have time to check into your trendy hotel in the Lower East Side before heading into midtown for a perfect early-evening stroll.
Ahead of a longer drive, eat breakfast at The Giacomo. The lounge serves a continental breakfast every morning, making for an ideal quick bite before you drive.
You’ll need a break for some food on the road, and Scranton is ideally located. Coney Island of Scranton has been around since 1923 and their famous hot dogs have stood the test of time. Drop in to grab one.
New York is one of the best cities in the world for foodies. For dinner, keep things close to your Lower East Side hotel and head over to Saigon Social. The spicy chicken sandwich is a standout!
Hit the road and drive from your hotel in Niagara Falls to NYC—it should take about six hours. Once you get there, dump your bags at the hotel and head to Central Park on the subway for a late afternoon/early evening walk.
New York may not be the cheapest city, but there are affordable hotels sprinkled around Manhattan. The Lower East Side is one of the coolest neighborhoods in the city and home to the Ludlow Hotel, a funky spot that features nearly 100 New York-style studio apartments at a good price.
East Side, Manhattan
A day in NYC
After a long day in the car, take your time exploring everything New York has to offer. From iconic art to fascinating architecture, live and breathe the city—with some great food mixed in, of course!
You’re not short on breakfast spots in Manhattan. But to keep things close to the hotel, head over to Essex Market. Hidden inside is Shopsin’s, a small, diner-style spot. The Adobe plate is a real treat!
For lunch, try out an NYC icon in Burger Joint. It’s usually packed around noon, but if you time it right, a mid-afternoon burger hits the spot.
Spaghetti Incident is an ideal dinner venue. The appeal is in the name as it’s home to some of the best pasta in the city.
Visit MoMA in the morning, taking in some of the most famous art in the world. For the quick hits, head up to the fifth floor. There you’ll find Van Gogh’s Starry Night, as well as other famous paintings by Picasso and Monet.
After lunch, head over to the Highline, 1.5 miles of public park in Manhattan. It’s a great spot to take in and explore the city. If you’ve got time, the Vessel, a tourist spot in Hudson Yards, is worth a visit.
Hudson Yards, Manhattan
From one iconic city to another: New York to Boston
Journey time: about 4 hours
Exchange New York for Boston as you move from one of America’s finest cities to another. Get going early and take in as much of Boston as you can throughout the afternoon and early evening—with some sports to finish it all off.
Drop into Katz’s Deli, right next door to The Ludlow Hotel. You’ll find iconic New York sandwiches that will keep you full for the drive.
Have lunch once you reach Boston, picking up a slice from Regina Pizzeria, a popular spot that’s been open for almost 90 years.
Dinner choices depend on whether you can make it to Fenway Park for a baseball game. But if you’re not gorging on hot dogs, give Shojo a go. The trendy Asian restaurant serves tasty bao.
Get going as early as your weary legs will allow and drive the four hours to Boston.
Once you get there, take in a Duck Boat tour, a timeless way of seeing the city. Late afternoon, check into your hotel before heading to see the USS Constitution, a dramatically preserved warship built in 1797.
If you can, try to snag tickets to see the Red Sox play at Fenway Park.
Try The Boxer, a funky building mirroring the architecture of the Flatiron in New York. It’s ideally located to explore the city.
An escape from city life: Boston to Acadia National Park
Journey time: about 4 1/2 hours
Switch city for country for the last time on the road trip as you head further into New England. Drive north through the rest of Massachusetts and into Maine, stopping at Acadia National Park, which sits right on the Atlantic Ocean.
Do breakfast quickly and early, grabbing coffee and pastries from Tradesman Coffee Shop and Bakery—they offer some of Boston’s best java.
Enjoy lunch with a view after a long drive. Munch on a sandwich and salad at Jordan Pond House, located just inside Acadia National Park.
The resort town of Bar Harbor offers plentiful dinner options—but being right on the ocean, it would be rude not to try some awesome seafood! For that, head to Geddy’s and give the scampi a go.
Leave Boston early and hit the road, driving through dramatic landscapes as you approach the northern reaches of New England. Once you arrive in Maine, take in some of the sights at Acadia National Park. Get the blood pumping with a walk to Otter Point in the late afternoon sun.
Settle down at the Inn on Mount Desert, a family owned and run boutique hotel a mile from the park border.
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A day in the outdoors: Acadia National Park
Finish your epic road trip with a day of hiking in Acadia. Make sure you’re properly equipped with safe hiking shoes and lots of water as you take in some fine Atlantic scenery.
Keep breakfast simple by fueling up from your hotel. You’ll need to be energized before being in the park all day.
For lunch, packed sandwiches will do. The Independent, in the center of Bar Harbor, does tasty takeout subs.
After a long day of walking, reward yourself with a big dinner at Side Street Cafe. The family-owned business serves fun spins on comfort food, with their lobster dishes standing out.
Acadia is easy to drive around, but it can’t be truly appreciated without using your legs. There are hundreds of miles of trails, and something for all ranges of abilities and hiking comfort.
Cadillac Mountain, the park’s highest point, is a good starting spot. For a solid loop, try the Cadillac Mountain North Ridge trail. It’s about four miles of easy walking with excellent views worked in. For something a little more challenging, the South Ridge trail is worth a look. It’s more strenuous and eight miles long.
Acadia National Park
Why you need roadside assistance
Road trips are great fun—until something goes wrong. Unfortunately, tires pop, batteries overheat, and collisions happen. It’s important to be prepared should any of those unfortunate situations arise.
Lucky for you, Jerry has a fantastic roadside assistance package. It features up to 10 miles of towing plus jump starts, tire changes, fuel deliveries, and more.
The package also comes with some exclusive benefits, including car advice, key replacement, and Uber credits. And it only costs $6.99 for one car!
The fast route back
After eight days of bustling cities and beautiful landscapes, you might not want to leave—and that’s perfectly fine! But the journey home is, unfortunately, inevitable.
The speediest route is a 19-hour slog through New Hampshire, Massachusetts, and then tracing the edge of the great lakes all the way into Chicago. It’s probably best split in half with a stop in pleasant Lenox, Massachusetts for the night.
The scenic route back
If it’s not time to go home just yet, you can always spend a few more days sauntering around.
Set off down to Portland, Maine. It’s an emerging New England city with lots to do, including a vibrant waterfront to walk, shop, and eat. Hang around there, enjoy some more sightseeing, and stay the night.
Next, head east through New Hampshire and Massachusetts. If you have time, veer off the road and check out the Mount Washington Auto Road in New Hampshire—a dramatic stretch home to the first car race in the United States.
Stop for the evening in the Catskill mountains at the Hotel Woodstock Way in Ulster County and get an extra day of hiking in.
At that point you can either drive the remaining 11 hours back to Chicago or spend the night in Pittsburgh, an intriguing option to break up the drive.
Finding cheap car insurance
No matter where you are or how far you’re driving, having the right car insurance to make sure you’re covered is vital. And car insurance comparison and broker app Jerry is here to help!
If you’re shopping for car insurance, Jerry will generate competitive quotes from top providers in less than a minute. Jerry gathers your information from your past insurer, so you’re not responsible for any long forms or phone calls. Basically, you get all of the savings and coverage, with none of the hassle.
The average Jerry user saves $897 per year on their car insurance!
“I was getting frustrated searching for cheaper insurance—then I found Jerry’s app. Less than 20 minutes later, I’m signed up for insurance that is saving me over $2,000 a year with equivalent coverage to my existing policy. They are also helping me cancel the old policy I had. Best app ever!” —Jerry user
What equipment do I need for the trip?
Just because you’re experiencing a lot of different landscapes doesn’t mean packing has to be a nightmare! For this one, it’s important to have the right hiking gear. That means you’ll need a solid pair of hiking shoes(tennis shoes or sneakers don’t usually do the trick), which you can find at any sports shop!
Also make sure you have a waterproof jacket and lightweight walking material. Although this is a road trip, you’ll be using your legs a lot!
What happens if I break down?
Well, we hope your car will serve you well for almost 1,500 miles. It’s important to put yourself in the best situation possible before leaving. Get your car serviced, have a full tank of gas, and check your tire pressure.
And if things go awry on the road, you’ll be glad you got Jerry’s roadside assistance program!
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