The Best Road Trip from Chicago to Maine

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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.
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Key trip details

Chicago, IL to Acadia National Park, ME
Chicago, IL to Acadia National Park, ME
​​Distance: 1,459 miles
Driving time: 24 hours
Suggested length of trip: 3 to 5 days
This is definitely a trip that requires some rest along the way, so why not take advantage of your drive and get the most out of every stop? Feel free to add time to any city on the way there or back.

Itinerary

  • Chicago, IL—1 day
  • Cleveland, OH—One half to 1 day
  • Niagara Falls, NY—1 day
  • New York City, NY—1 to 2 days
  • Boston, MA—One half to 1 day
  • Acadia National Park, ME—1 to 2 day

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.

Where to stay in Chicago

  • emc2 Chicago: Bed in for the night at this trendy hotel in the heart of the famous Magnificent Mile. It’s a boutique hotel with comfy, modern rooms and easy accessibility to the rest of Chicago. Cost per night: from $294.

Where to eat in Chicago

  • Batter and Berries ($$): The unassuming streetside spot is famous for its rotating and innovative recipes for french toast, so you’ll always have something different to try!
  • Nhu Lan ($): Grab a quick lunch at this bakery for some delicious banh mi. Their affordable sandwiches are some of the best around!
  • Pleasant House ($$): Finish your day 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.

What to do in Chicago

An oxidized sculpture of a lion stands outside of The Art Institute of Chicago.
The Art Institute of Chicago
  • Field Museum: Stroll around this iconic Chicago cultural experience and take in one of the best natural history museums in the world, with exhibitions focusing on dinosaurs, ancient Egypt, gems, and so much more.
  • Art Institute of Chicago: Housing an impressive collection that spans centuries and nations, it’s worth spending an afternoon in their halls. This fine museum also now has the portraits of Barack and Michelle Obama adorning its walls.
  • Chicago Cubs game at Wrigley Field: To finish off your cultural experience, you’ll want to take in a Cubs game! It’s the second-oldest venue in Major League Baseball and well worth the trip for the ambiance and hot dogs alone!

Chicago to Cleveland

346 miles, 5.5 hours
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!
To get to Cleveland, follow the I-90 E and take exit 172 A.

Where to stay in Cleveland

  • Glidden House: For a blend of modern comfort and progressive-era architecture, spend the night at this full-service boutique hotel located in a mansion dating back to the 1910s! Cost per night: from $159.

Where to eat from Chicago to Cleveland

  • M. Henry ($$): Hit up this Chicago spot for breakfast before you hit the road! Their drunken eggs are a hit, but if you want to get going quickly, they also offer carry-out pastries and coffee. Grab something for lunch, too, since you’re in for a bit of a drive to Cleveland.
  • Momocho ($$): There are loads of good restaurants in Cleveland, and one of the best is Momocho! Offering an innovative, modern take on Mexican fare with a nice outdoor patio.

What to do from Chicago to Cleveland

A view looking down a sand path at Indiana Dunes National Park.
Indiana Dunes National Park
  • Indiana Dunes National Park: On your way to Cleveland, take a detour here! 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!
  • West Side Market: Stroll through Cleveland’s public oldest market, home to over 100 vendors offering local, fresh produce, baked goods, handmade clothing and jewelry, and so much more!

Cleveland to Niagara Falls

213 miles, 3.5 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.
Continue on the I-90 E and take exit 22 to arrive in Niagara Falls!

Where to stay in Niagara Falls

  • The Giacomo: Spend your night in this comfy, art deco-style hotel close to Niagara Falls. This location lets you walk to the Falls, the Maid of the Mist, and even Niagara Falls State Park. Cost per night: from $121.

Where to eat from Cleveland to Niagara Falls

  • Luna Cafe ($$): You’ll want to make the most out of your day’s activities, so go for a quick breakfast at this cafe—their crepes and paninis are especially yummy!
  • Mabel’s BBQ ($$): For a hearty lunch to fill you up for the road, look no further than this Cleveland hotspot that serves up fantastic mac n cheese, paired with delicious smoked meats.
  • Griffon ($$): Food options in Niagara Falls are plentiful, but for a more interesting experience check out this gastropub. Their Aukra salmon served on top of ginger rice is a hit.

What to do from Cleveland to Niagara Falls

The end of a rainbow falls onto the swirling blue water of Niagara Falls on a sunny day. A tour boat glides through the water.
Niagara Falls
  • Rock & Roll Hall of Fame: Visit this music museum in the morning—and inevitably argue about the inclusion, or, perhaps, exclusion of some artists. Admission is $26 for adults, but this is a must-see for any music enthusiasts.
  • Niagara Falls: If you’ve never been to Niagara Falls before, then prepare yourself to be awestruck! 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.
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Niagara to NYC

408 miles, 6.5 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.
Take the I-90 E, I-81 S, I-380 S, I-80 E, and I-280 E to Holland Tunnel in Jersey City.

Where to stay in New York City

  • Ludlow Hotel: The Lower East Side is one of the coolest neighborhoods in the city and home to the Ludlow, a funky spot that features nearly 100 New York-style studio apartments at a good price. Cost per night: from $249.

Where to eat from Niagara to New York City

  • Coney Island of Scranton ($): 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.
  • Saigon Social ($$): For dinner, keep things close to your Lower East Side hotel and head over to this fantastic Vietnamese spot. The spicy chicken sandwich is a standout!

What to do from Niagara to New York City

  • Stroll through Central Park: Once you get to New York, you'll definitely want to stretch your legs! Dump your bags at the hotel and head to the iconic Central Park on the subway for a late afternoon/early evening walk.

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!

Where to eat in New York City

  • Shopsin’s ($): To keep things close to the hotel, head over to this small, diner-style spot hidden inside Essex Market. Their vast selection of pancakes is impressive and the Adobe plate is a real treat!
  • Spaghetti Incident ($$): An ideal dinner venue to end the night, this spot is home to some of the best pasta in the city. Stop here for a cozy, authentic dining experience.

What to do in New York City

Starry Night on display at Museum of Modern Art.
Museum of Modern Art
  • Museum of Modern Art: The MoMA is a must-see while in the Big Apple, and visiting lets you take 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.
  • Highline: Taking a stroll through this public park in Manhattan, stretching over 1.5 miles, is a great way to take in and explore the city.
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From one iconic city to another: New York to Boston

217 miles, 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.
To get to Boston, take the I-95 N, I-91 N, I-84 E, and I-90 E until you reach exit 17.

Where to stay in Boston

  • The Boxer: Stay at this funky building designed to mirror the architecture of the Flatiron in New York. It has premium accommodations and amenities and is ideally located to explore the city. Cost per night: from $152.

Where to eat from New York City to Boston

  • Katz’s Delicatessen ($$): Drop into this well-loved deli located right next door to The Ludlow Hotel. You'll find iconic mile-high New York sandwiches that will keep you full for the drive.
  • Regina Pizzeria ($): Choose any item off the menu from this popular Boston spot and you won’t be disappointed! It’s been open for almost 90 years and serves some of the best brick oven pizza you’ll ever have.
  • Shojo ($$): Located in downtown Boston’s Chinatown neighborhood, Shojo serves up modern, inventive takes on Asian cuisine and has a number of creative cocktails and Japanese spirits offered as well.

What to do from New York City to Boston

Two kids feed ducks near the Swan boats on the Boston Common.
Swan boats on the Boston Common
  • Duck Boat Tour: If you’re looking for the best, most timeless way to see Boston, then be sure to book this tour that takes you through both land and water to deliver an epic tour experience.
  • USS Constitution: First built in 1797, touring this dramatically preserved warship makes for an interesting, enlightening afternoon—it’s a must-do for any history buffs!

An escape from city life: Boston to Acadia National Park

280 miles, 4.5 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.
To get to your final destination, continue on the I-95 N, taking the I-295 N and I-95 N until you reach exit 6A.

Where to stay in Acadia National Park

  • Inn on Mount Desert: Settle down at this family-owned and operated boutique hotel located only a mile from the park border. The rooms are comfy, featuring a coastal motif, and it’s the perfect place to rest after your long road trip. *Cost per night: from $140.**

Where to eat from Boston to Acadia National Park

  • Tradesman Coffee Shop and Lounge ($$-$$$): Do breakfast quickly and early, grabbing coffee and pastries from this cozy, welcoming cafe—they offer some of Boston’s best java and yummiest pastries.
  • Jordan Pond House ($$$): Munch on a sandwich and salad at this restaurant located just inside Acadia National Park. You can enjoy your lunch with a view after your long drive.
  • Geddy’s ($$): You can find this amazing seafood spot in the nearby town of Bar Harbor. The food is all amazingly fresh and locally sourced—we recommend giving the scampi a go!

What to do in Acadia National Park

A nighttime bonfire gives pine trees an orange glow. To the right, two tents sit side by side at Acadia National Park.
Acadia National Park
  • Take in Acadia National Park: There are a number of awesome things to do in this gorgeous coastal park. Whether that’s completing some hikes, biking the carriage roads, watching the sunrise, or driving Park Loop Road—there really are endless things to do and see while here!

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.

Where to eat in Acadia National Park

  • The Independent ($): Pick up some delicious takeout subs and a cup of coffee from this Bar Harbor spot to keep yourself fueled and energized for the day!
  • Side Street Cafe ($$): After a long day of walking, reward yourself with a big dinner at this Bar Harbor staple. The family-owned business serves fun spins on comfort food, with their lobster dishes standing out.

What to do in Acadia National Park

  • Cadillac Mountain North Ridge trail: For a solid loop, try this trail found on Cadillac Mountain, the park’s highest point! It’s about four miles of easy walking with excellent views worked in.
  • Cadillac Mountain South Ridge trail: For something a little more challenging, this hike is definitely worth trying out. It’s more strenuous and is eight miles long, but it provides some views of the scenery that just can’t be beaten.

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.
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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!
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FAQs

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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