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Chicago, IL, USA to Boston, MA, USA from $40: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Boston, United States of America

How to Get from Chicago to Boston: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$40 by trainBest price
1372 kmDistance
3h 58m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Boston with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Average Duration
3h  58m
Estimated price
$88-617
Recommended
Company
Amtrak
Train
Average Duration
22h  2m
Estimated price
$40-300
Cheapest
route map
Distance: 1372 km
Duration: 3h 58m

See more options

Company
various
Plane
Average Duration
4h  19m
Estimated price
$62-287
Company
various
Plane
Average Duration
5h  41m
Estimated price
$96-502
Company
various
Plane
Average Duration
5h  40m
Estimated price
$120-857
Company
various
Plane
Average Duration
6h  11m
Estimated price
$160-727
Company
various
Plane
Average Duration
5h  30m
Estimated price
$168-440
Company
N/A
Drive
Average Duration
16h  33m
Estimated price
$180-270
Company
various
Bus
Average Duration
22h  33m
Estimated price
$206-294
Browse car rentalsExplore flights

Traveling From Chicago to Boston

Traveling from Chicago, a bustling Midwestern hub known for its architecture and deep-dish pizza, to Boston, steeped in American history and coastal charm, offers travelers an opportunity to experience two distinctly vibrant cities.

Best Neighbourhoods in Boston

Boston’s neighborhoods each showcase a unique blend of culture and history.

Back Bay
• Famous for its stunning Victorian brownstones.
• Home to upscale shopping on Newbury Street.
North End
• Renowned for authentic Italian cuisine and bakeries.
• Rich in history, with the oldest streets in Boston.
Beacon Hill
• Notable for its historic cobblestone streets.
• Offers picturesque views and charming gas lamps.

Best Times To Visit Boston's Attractions

Timing your visit can greatly enhance your experience in Boston's top attractions.

Freedom Trail
Visit early in the morning or late afternoon for a quieter stroll.
Fenway Park
Attend weekday games for fewer crowds and a relaxed atmosphere.
Harvard University
Explore during the summer for serene campus tours and pleasant weather.

Boston Weather: What to Expect Year-Round

Boston experiences a humid continental climate with cold winters and warm summers, making spring and fall the best times to visit for pleasant weather and vibrant foliage. The changing seasons can significantly affect your travel experience, from winter sports and holiday festivities to summer outdoor events.

Dining Recommendation in Boston

Try the classic New England clam chowder at Union Oyster House, the oldest continuously operating restaurant in the United States. Unlike Chicago’s hearty deep-dish pizza, this creamy, savory soup showcases fresh local seafood and offers a cozy atmosphere that immerses you in Boston's rich maritime history.

Chicago - Boston operators

Explore transport companies operating between Chicago and Boston, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights
Website
southwest.com

Plane from Chicago Midway (MDW) to Boston (BOS)

Average Duration
3h 58m
Estimated price
$88-617
Website
delta.com

Plane from Chicago Midway (MDW) to Boston (BOS)

Average Duration
3h 58m
Estimated price
$85-650

Plane from Chicago O'Hare (ORD) to Boston (BOS)

Average Duration
2h 21m
Estimated price
$120-370
Website
aa.com

Plane from Chicago O'Hare (ORD) to Boston (BOS)

Average Duration
2h 24m
Estimated price
$80-350
Website
united.com

Plane from Chicago O'Hare (ORD) to Boston (BOS)

Average Duration
2h 21m
Estimated price
$100-440
Website
jetblue.com

Plane from Chicago O'Hare (ORD) to Boston (BOS)

Average Duration
2h 25m
Estimated price
$90-380
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Boston

Average Duration
22h 2m
Estimated price
$40-300
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$3-75
Bus Show bus routes
Website
palmlandlines.com

Bus from Chicago IL to Indianapolis IN

Average Duration
3h 20m
Estimated price
$50-65
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from New York Midtown to Boston

Average Duration
4h 20m
Estimated price
$19-70
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Indianapolis IN to New York

Average Duration
11h
Estimated price
$130-130

Chicago to Boston: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Boston offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on an epic road trip from Chicago to Boston, covering a total driving distance of 997 miles. The journey offers a scenic route through the heart of the Midwest and the East Coast, showcasing the diverse landscapes of America. 💸 Prices for the road trip from Chicago to Boston range from $180 to $270, allowing flexibility for different budgets. Along the way, you can enjoy the freedom of the open road, stopping at charming towns and landmarks, and indulging in local cuisine and culture. 🌆 Arrive in vibrant Boston after approximately 16 hours and 33 minutes of driving, ready to explore the historic streets, iconic landmarks, and bustling neighborhoods of this East Coast gem.
Average price
$180 - $270
🚆 Embark on a scenic train journey from Chicago Union Station to Boston, enjoying a leisurely ride that takes approximately 22 hours and 2 minutes. Operated by Amtrak, this daily service offers a comfortable and convenient way to travel between the two bustling cities. 🌆 Traverse a distance of 1,017 miles as you make your way from Chicago to Boston aboard the Lake Shore Limited train. With an assortment of amenities onboard, including stunning views and ample seating, the journey promises a relaxing experience for passengers. 🚉 Experience the charm of train travel with two transfers on an alternate route, taking you on a scenic adventure through diverse landscapes. Admire the countryside as you pass through various stations, culminating in your arrival at Boston's South Station after a memorable 1 day and 2 hours journey.
Departure Point
Chicago Union Station
Arrival Point
Boston station
Useful tips for train travellers
• On your train trip from Chicago to Boston, consider Amtrak as the primary operator for this route. Amtrak offers a variety of onboard services including a café car where you can purchase snacks, beverages, and light meals. Additionally, if you are in the Business Class or First Class, you may receive complimentary meals and drinks served at your seat.
• The Amtrak Lake Shore Limited train operates between Chicago and Boston, providing several seating options. In Economy class, you can choose from standard coach seating, which is comfortable yet basic. If you’re looking for more comfort, consider upgrading to Business class, which offers wider seats and more legroom. First Class is typically not available on this route, but in Business class, expect additional amenities like priority boarding and access to the lounge in some stations.
• Upon arriving at Boston's South Station, you can easily access local transportation options. The station provides luggage storage services for a fee, so you don't have to carry your bags around if you plan to explore the city right after your arrival. Showers are not available at the station, but restrooms are easily accessible. For the fastest way to get to the city center, take the MBTA’s Red Line from South Station. It’s just a few steps from the train platforms and will get you to Park Street station in about 5 minutes, where you can transfer to other lines if needed.
🛫 Experience a convenient and quick journey from Chicago to Boston with a direct flight taking only 2 hours and 10 minutes. Choose from reputable airlines like Delta and Southwest for a smooth trip. 🏙️ Upon landing in Boston, after a short flight of 3 hours and 58 minutes, immerse yourself in the rich history and vibrant atmosphere of this iconic East Coast city. 💸 Enjoy the flexibility of flight prices ranging from $88 to $617 for a round trip between Chicago and Boston, making it accessible for various budgets.
Departure Point
Chicago Midway Airport
Arrival Point
Boston Airport
Useful tips for plane travellers
• Be prepared for potential weather changes; Boston’s unpredictable climate can result in delays during fall and winter, so consider booking a later flight to avoid being affected by these conditions.
• Upon arrival at Boston Logan International Airport (BOS), take advantage of the airport's free Silver Line bus service, which provides direct transport to South Station and the city center; this can save you significant taxi fare.
• Expect taxi fares from Boston Logan to downtown to range from $25 to $35; also, consider apps like Uber or Lyft to compare prices and avoid the frustration of parking if you're renting a car.
🚌 Embark on a scenic bus journey from Chicago to Boston, with transfers in Indianapolis, New York City Chinatown, and New York Midtown. The total travel time, including transfers, is approximately 22 hours and 33 minutes. 🛣️ Route options vary in duration, with distances between 1,093 to 1,162 miles and 2 to 3 transfers along the way. Passengers can expect stops in cities like Cleveland, New York, and possibly other locations before reaching Boston. 💰 Ticket prices range from $206 to $294 for this extensive bus adventure from the vibrant streets of Chicago to the historic landmarks of Boston. Prepare for a comfortable ride and enjoy the diverse scenery as you make your way to your final destination.
Departure Point
Chicago IL station
Arrival Point
Boston station
Useful tips for bus travellers
• Consider downloading the FlixBus and Greyhound apps for up-to-date schedules, boarding information, and mobile ticketing before your trip, as you'll be using their services on this route: flixbus.com and greyhound.com
• While transferring in New York City, take advantage of the 45-minute break to grab a quick meal or coffee; check out nearby options like Xi'an Famous Foods for delicious hand-pulled noodles, located at 67 Bayard St, just a 10-minute walk from the Port Authority Bus Terminal.
• Upon arrival at Boston's South Station, use the interactive maps available at the station to locate nearby subway connections for easy access to the rest of the city, including the Red Line to Cambridge or the Silver Line for the airport: mbta.com

Frequently asked questions

Find out more about the route from Chicago to Boston.

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The cheapest way to travel from Chicago to Boston is by train. Amtrak offers several options, including the Lake Shore Limited route which takes approximately 22 hours and 2 minutes. Prices for train tickets range from $40 to $300, depending on the time of year and class of service chosen. While it may not be the fastest option, it is a cost-effective and scenic way to travel between these two cities.
The fastest way to travel from Chicago to Boston is by flying. There are direct flights available which can take approximately 4 hours and 6 minutes. The cost of the flight can vary between $75 to $500, depending on the airline and time of booking. Airlines such as American Airlines, United Airlines, and Delta Air Lines offer regular flights between the two cities.
It is approximately 853 miles from Chicago to Boston. If you choose to drive, the distance is approximately 997 miles. However, keep in mind that the actual distance may vary depending on the route you take. It is important to factor in traffic and road conditions when planning your trip.
The most convenient and affordable way to travel from Chicago to Boston without a car is by taking a bus. There are several bus companies that offer direct routes between the two cities, with journey times typically ranging from 19 to 24 hours. The cost of a bus ticket can vary depending on the provider and the time of travel, but fares usually range from $14 to $150. It is recommended to book your bus ticket in advance to secure the best prices and ensure availability.
The travel time from Chicago to Boston is approximately 4 hours and 6 minutes, depending on the mode of transportation and any potential transfers. This is based on an average travel time and may vary depending on specific circumstances. It is recommended to check with the specific mode of transportation for the most accurate and up-to-date travel time information.
The most convenient and fastest way to travel from Chicago to Boston is by flying, with a travel time of approximately 4 hours and 6 minutes. Flights can range in price from $75 to $500 depending on the airline and when you book. If you are looking for a more affordable option, you can consider taking a bus, which takes around 19 hours and 5 minutes and costs between $14 and $150. Another option is to travel by train, with a travel time of approximately 22 hours and 2 minutes and ticket prices ranging from $40 to $300.
There are plenty of accommodation options available near Boston. With over 808 hotels to choose from, you will have no shortage of choices. Prices start at $73 per night, making it accessible for various budgets. Whether you prefer luxury hotels, boutique accommodations, or budget-friendly options, you should be able to find a suitable place to stay near Boston.
Yes, you can drive from Chicago to Boston. The driving distance between the two cities is 997 miles. It takes approximately 16 hours and 33 minutes to drive from Chicago to Boston, depending on the traffic and stops along the way. Keep in mind that gas, tolls, and potential overnight accommodation costs should also be factored into your budget when considering this option.
Yes, there is no direct bus from Chicago to Boston. However, there are bus services available that include transfers. The journey typically involves departing from Chicago and transferring in Ithaca, NY before reaching Boston. The total travel time for this route is approximately 19 hours and 5 minutes.
To catch the bus from Chicago to Boston you will need to go to the Chicago station. This is where the bus services, operated by OurBus, depart from. Make sure to check the schedule and arrive at the station in advance to avoid missing your departure time.
The Chicago to Boston bus arrives at the Boston station. This bus service is operated by OurBus. The exact arrival location may vary depending on the specific bus route and schedule, but it will be in the city of Boston. The bus stations in Boston are well-connected and easily accessible for onward travel within the city.
To get to Boston from the airport, you can take the Silver Line bus service from Boston Logan International Airport. The bus operates every 10 minutes and takes around 20-30 minutes to reach downtown Boston. The fare for the Silver Line bus is $2.8 per person. Alternatively, you can also take a taxi or use a ridesharing service, which will take approximately 15-30 minutes depending on traffic conditions, and cost around $25-$40.
Southwest Airlines is the only airline that offers direct flights between Chicago and Boston. Their flights operate from Chicago Midway Airport to Boston Airport. It is recommended to check the airline's website or flight booking platforms for the most up-to-date information on schedules and pricing. Keep in mind that other airlines may offer connecting flights between the two cities as well.
The quickest way to travel from Chicago to Boston is by taking a direct flight. The flight duration from Chicago Midway Airport to Boston Airport is approximately 2 hours and 10 minutes. Southwest Airlines offers flights on this route. The prices for flights between Chicago and Boston range from $78 to $501 depending on the airline and time of booking.
The flight from Chicago to Boston typically takes around 2 hours and 10 minutes for a direct flight. However, this can vary depending on factors such as the airline, route, and any layovers. It's worth noting that flight times can sometimes be subject to delays due to weather conditions or air traffic. It's always recommended to check with the airline for the most accurate and up-to-date information regarding your specific flight.
Trains from Chicago to Boston arrive at the Boston station. This is the main train station in Boston, conveniently located in the city center. It is served by various Amtrak train services, providing a convenient and accessible transportation option for travelers. The Boston station offers connections to other modes of transportation such as buses and taxis, making it easy to reach your final destination.
Yes, there is a direct train between Chicago and Boston. The train departs from Chicago Union Station once daily and operates every day. The journey takes approximately 22 hours and 2 minutes. This direct train provides a convenient and hassle-free way to travel between the two cities without the need for transfers or layovers.
To catch the train from Chicago to Boston head to Chicago Union Station. Amtrak operates train services from this station to Boston. Make sure to arrive at the station ahead of time to check-in and board the train. The train journey takes approximately 22 hours and 2 minutes.
The cost of a flight from Chicago to Boston typically ranges between $78 to $501. The prices can vary depending on factors such as the airline, time of booking, and availability of seats. It is recommended to compare prices from different airlines and use travel comparison websites to find the best deals for your specific travel dates.
The cost of a train ticket from Chicago to Boston can range from $40 to $300, depending on factors such as the type of train, class of service, and time of booking. Prices may also vary based on availability and demand. It is recommended to book your train ticket in advance to secure the best possible fare.
The cost of a bus ticket from Chicago to Boston can range from $14 to $146. The exact price depends on factors such as the bus company, the time of travel, and the seating class chosen. It is recommended to check with different bus companies and compare prices to find the best deal.
The cost of driving from Chicago to Boston will depend on various factors such as the distance, gas prices, tolls, and the vehicle's fuel efficiency. On average, the estimated cost ranges from $180 to $270 for a one-way trip. It's important to consider additional expenses like food, accommodation, and parking fees. It is recommended to calculate the costs based on your specific route and vehicle to get a more accurate estimation.

Trips from Chicago