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Boston, MA, USA to Chicago, IL, USA from $40: 10 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Boston, United States
to
Chicago, United States

How to Get from Boston to Chicago: 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
4h 22m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Boston to Chicago 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
4h  22m
Estimated price
$89-632
Recommended
Company
Amtrak
Train
Average Duration
22h  22m
Estimated price
$40-300
Cheapest
route map
Distance: 1372 km
Duration: 4h 22m

See more options

Company
Various
Plane
Average Duration
4h  41m
Estimated price
$64-302
Company
Various
Plane
Train
Average Duration
6h  54m
Estimated price
$97-518
Company
Various
Train
Plane
Average Duration
5h  28m
Estimated price
$119-849
Company
Various
Train
Plane
Average Duration
6h  1m
Estimated price
$159-719
Company
Various
Bus
Plane
Average Duration
5h  17m
Estimated price
$168-439
Company
Self
Drive
Average Duration
16h  30m
Estimated price
$180-270
Company
Flixbus USA
Bus
Average Duration
22h  49m
Estimated price
$204-295
Company
Various
Bus
Plane
Average Duration
5h  33m
Estimated price
$228-519
Browse car rentalsExplore flights

Traveling From Boston to Chicago

Journeying from Boston to Chicago offers you a shift from the coastal charm and historic streets of New England to the Midwestern vibrancy and iconic architecture of the Windy City.

Best Neighbourhoods in Chicago

Chicago boasts diverse neighborhoods, each offering distinct experiences and attractions.

Wicker Park
• Trendy shops and cafés line the vibrant streets.
• A hub for live music and art events.
Lincoln Park
• Expansive park areas and beautiful lakefront views.
• Home to the renowned Lincoln Park Zoo.
The Loop
• Chicago's bustling business district with stunning architecture.
• Close to theaters, museums, and Millennium Park.

Best Times To Visit Chicago's Attractions

Timing your visits can significantly enhance your experience at Chicago's top sites.

Millennium Park
Early mornings on weekdays offer a serene atmosphere and fewer crowds.
Art Institute of Chicago
Visit on Thursdays in the afternoon for less foot traffic and broader gallery access.
Willis Tower Skydeck
Late afternoons on weekdays provide stunning sunset views and shorter lines.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with hot summers and cold winters, making each season uniquely enjoyable. Planning your visit during late spring or early fall often brings comfortable temperatures and vibrant city life, enhancing your travel experience.

Dining Recommendation

Visit Lou Malnati's Pizzeria for an unforgettable deep-dish pizza experience that showcases Chicago's signature style, rich with gooey cheese and hearty toppings. This contrasts with Boston's seafood-centric cuisine, offering you a chance to savor a savory, comforting dish in a lively, casual atmosphere that's distinctly Chicago.

Boston - Chicago operators

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

Plane Show flights
Website
southwest.com

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

Average Duration
2h 47m
Estimated price
$110-260
Website
aa.com

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

Average Duration
3h 1m
Estimated price
$80-350
Website
delta.com

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

Average Duration
4h 35m
Estimated price
$150-470

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

Average Duration
3h 3m
Estimated price
$120-360
Website
united.com

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

Average Duration
3h 1m
Estimated price
$100-440
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Boston to Chicago Union Station

Average Duration
22h 22m
Estimated price
$40-300
Bus Show bus routes
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Boston to New York Midtown

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

Bus from Boston to Boston Manchester Airport

Average Duration
1h 5m
Estimated price
$5-35

Bus from New York to Indianapolis, IN

Average Duration
11h 15m
Estimated price
$130-130
Website
palmlandlines.com

Bus from Indianapolis, IN to Chicago IL

Average Duration
3h 20m
Estimated price
$50-65

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

Traveling between Boston and Chicago 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 a scenic road trip from Boston to Chicago, covering a distance of 1601.3 km, which will take you around 16 hours and 30 minutes of driving time. 💰 Explore budget-friendly options for your car trip, with prices ranging from $180 to $270 for the ride from Boston to Chicago.
Average price
$180 - $270
🚆 Embark on a scenic train journey from Boston to Chicago aboard Amtrak. With services operating daily, enjoy a comfortable 22-hour and 22-minute ride from Boston station to Chicago Union Station. 🛤️ Choose from different routes with varying durations and transfers. Whether opting for a direct ride or a multi-step journey, sit back and relax as you cover the 1915.1 km distance between these vibrant cities by rail.
Departure Point
Boston station
Arrival Point
Chicago Union Station
Useful tips for train travellers
• On your train journey from Boston to Chicago, Amtrak offers catering services through its Café Car. You can purchase a range of snacks, beverages, and light meals during the trip; some popular options include sandwiches, salads, and iconic Amtrak treats like cookies. Make sure to check the menu upon boarding for availability.
• Amtrak operates the Cardinal and Lake Shore Limited routes between Boston and Chicago, offering a variety of seating options. You can travel in First Class with more spacious and comfortable seating, Business Class with amenities such as complimentary beverages, or Economy Class if you prefer a budget-friendly option. Each class has its own features, so choose based on your comfort and budget.
• Upon arrival at Chicago Union Station, expect to find a bustling environment with multiple transit options. Union Station does not have luggage storage, but you can make use of the restrooms located throughout the station. For a quick transfer to the city center, take the CTA 'Blue Line' train directly from the station, which will get you to downtown Chicago in about 45 minutes.
🛫 Flying from Boston to Chicago is made convenient by taking a direct flight that typically lasts 2 hours and 45 minutes, making it a quick journey. 🌆 The total flight duration from Boston to Chicago is approximately 4 hours and 22 minutes, allowing passengers to reach their destination efficiently. Prices for flights between the two cities can range from $89 to $632, offering a variety of options for different budgets.
Departure Point
Boston Airport
Arrival Point
Chicago Midway Airport
🚌 The journey from Boston to Chicago by bus includes transfers in New York Midtown, New York, Lafayette Rd & 37th St, and Indianapolis IN, taking approximately 22 hours and 49 minutes. 🌆 Route options vary, with distances ranging from 1705.9 km to 1755.8 km and 2 transfers required on each route. Greyhound and other bus agencies operate the services along the way. 💰 Prices for the Boston to Chicago bus trip range from $204 to $295, offering budget-friendly travel options for those exploring the East to Midwest route.
Departure Point
Boston station
Arrival Point
Chicago IL station

Frequently asked questions

Find out more about the route from Boston to Chicago.

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The distance between Boston and Chicago is approximately 1372.8 km. The typical travel times by various modes of transportation vary. It takes about 22 hours and 22 minutes to reach Chicago from Boston by train, 5 hours and 7 minutes by taking a bus to Manchester and then flying to Chicago Midway, and 4 hours and 7 minutes by plane. Conversely, it takes around 16 hours and 30 minutes to drive from Chicago to Boston and about 17 hours and 45 minutes by bus.
To travel from Boston to Chicago the most cost-effective option would be to take the train. With prices ranging from $40 to $300, it takes approximately 22 hours and 22 minutes to reach Chicago. For a quicker alternative, flying would be the best option, costing around $75 to $500 and taking only 4 hours and 7 minutes.
The prices for traveling from Boston to Chicago vary depending on the mode of transportation. By train, prices range from $40 to $300, while bus tickets range from $14 to $147.
To get from Boston to Chicago without using public transportation, you can drive the distance of approximately 1601.3 km. The journey usually takes around 16 hours and 30 minutes by car. The cost of this option could range from $180 to $270, depending on factors such as gas prices and tolls.
The best way to travel from Boston to Chicago without a car is by taking a bus. It takes approximately 17 hours and 45 minutes and costs between $14 and $150. Another option is to fly, which takes around 4 hours and 7 minutes and costs between $75 and $500. Alternatively, you can also take a train which takes 22 hours and 22 minutes and costs between $40 and $300.
Yes, there is a direct train link between Boston and Chicago. The train journey takes approximately 22 hours and 22 minutes and operates once daily. There is no direct bus service between the two cities, but buses are available with a transfer in Ithaca, NY, taking approximately 17 hours and 45 minutes.
The flight from Boston to Chicago typically takes around 2 hours and 30 minutes. However, the duration may vary depending on factors such as weather conditions and the specific airline. As for the cost, prices for a flight between Chicago and Boston can range from $79 to $501.
There are numerous accommodation options available near Chicago. With over 1116 hotels to choose from, visitors can find options suitable for all budgets and preferences. Prices start at $58 per night, providing a range of affordable choices for travelers.