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There are 10 ways to get from Boston to Chicago by plane, bus, train or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Boston to Chicago Midway  •  4h 10m

  1. Fly from Boston (BOS) to Chicago Midway (MDW) BOS - MDW

$89 - $6,515

Cheapest option

Fly Boston to Chicago O'Hare  •  4h 28m

  1. Fly from Boston (BOS) to Chicago O'Hare (ORD) BOS - ORD

$21 - $285

8 alternative options

Bus to Manchester, fly to Chicago Midway  •  5h 1m

  1. Take the bus from Boston South Buses to North Londonderry, NH - exit 5
  2. Fly from Manchester (MHT) to Chicago Midway (MDW) MHT - MDW

$260 - $534

Bus to Manchester, fly to Chicago O'Hare  •  5h 37m

  1. Take the bus from Boston South Buses to North Londonderry, NH - exit 5
  2. Fly from Manchester (MHT) to Chicago O'Hare (ORD) MHT - ORD

$95 - $324

Train to Providence, fly to Chicago Midway  •  5h 33m

  1. Take the train from Boston South Station to Providence Amtrak Station
  2. Fly from Providence (PVD) to Chicago Midway (MDW) PVD - MDW

$211 - $873

Train to Providence, fly to Chicago O'Hare  •  6h 1m

  1. Take the train from Boston South Station to Providence Amtrak Station
  2. Fly from Providence (PVD) to Chicago O'Hare (ORD) PVD - ORD

$91 - $493

Bus  •  20h

  1. Take the bus from Boston South Buses to New York Boston
  2. Take the bus from New York to Chicago, IL Wdt 205

$90 - $150

Train  •  22h

  1. Take the train from Boston South Station to Chicago Union Station Lake Shore Limited

$100 - $150

Bus via New York  •  23h 45m

  1. Take the bus from South Station, Boston, MA to Port Authority Bus Terminal, New York, NY Peter Pan / ...
  2. Take the bus from New York, Ny to Chicago Amtrak, Il 4425

$113 - $168

Drive  •  16h 32m

  1. Drive from Boston to Chicago 996.4 miles

$95 - $150

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Some travel restrictions may still be in place within United States. For the latest travel status, please check the official page for United States.

For travel planning advice, please refer to our Rome2rio Coronavirus information page .
For the latest travel status, we recommend checking the official page for United States.

Coronavirus (COVID-19) Travel Advice

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Official Coronavirus (COVID-19) Information for United States

Currently, we are unable to provide domestic travel restriction information for travelling within United States. For the latest Coronavirus (COVID-19) travel status within United States, please check government recommendations.

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Official Coronavirus (COVID-19) Information for United States

Last updated: June 29 | Data sourced from: ACAPS, OXFORD

Questions & Answers

The cheapest way to get from Boston to Chicago is to fly which costs $20 - $290 and takes 4h 28m.

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The quickest way to get from Boston to Chicago is to fly which costs $85 - $6,500 and takes 4h 10m.

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No, there is no direct bus from Boston to Chicago. However, there are services departing from Boston South Buses and arriving at Chicago, IL via New York. The journey, including transfers, takes approximately 20h.

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Yes, there is a direct train departing from Boston South Station station and arriving at Chicago Union Station station. Services depart once daily, and operate every day. The journey takes approximately 22h.

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The distance between Boston and Chicago is 853 miles. The road distance is 996.4 miles.

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The best way to get from Boston to Chicago without a car is to bus which takes 20h and costs $90 - $150.

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It takes approximately 4h 10m to get from Boston to Chicago, including transfers.

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Boston to Chicago bus services, operated by Peter Pan Bus Lines, depart from South Station, Boston, MA.

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Boston to Chicago train services, operated by Amtrak, depart from Boston South Station.

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The best way to get from Boston to Chicago is to fly which takes 4h 10m and costs $85 - $6,500. Alternatively, you can bus, which costs $90 - $150 and takes 20h, you could also train, which costs $100 - $150 and takes 22h.

Mode details

Map of how to get from Boston to Chicago.
Launch map view
  • Distance: 853.4 miles
  • Duration: 4h 10m

What companies run services between Boston, MA, USA and Chicago, IL, USA?

Southwest Airlines, Delta and Porter Airlines fly from Boston to Chicago hourly. Alternatively, you can take a bus from Boston to Chicago via New York in around 20h.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Boston to Chicago Midway
Ave. Duration
2h 42m
When
Every day
Estimated price
$85 - $1,000
Flights from Boston to Chicago Midway via Columbus
Ave. Duration
4h 15m
When
Monday to Friday
Estimated price
$85 - $1,000
Flights from Boston to Chicago Midway via Baltimore
Ave. Duration
4h 27m
When
Monday to Saturday
Estimated price
$85 - $1,000
Flights from Manchester to Chicago Midway
Ave. Duration
2h 23m
When
Every day
Estimated price
$330 - $460
Flights from Manchester to Chicago Midway via Baltimore
Ave. Duration
5h 7m
When
Every day
Estimated price
$330 - $460
Flights from Providence to Chicago Midway
Ave. Duration
2h 24m
When
Every day
Estimated price
$200 - $800
Flights from Providence to Chicago Midway via Baltimore
Ave. Duration
4h 16m
When
Monday to Friday
Estimated price
$200 - $800
Flights from Providence to Chicago Midway via Reagan Washington
Ave. Duration
4h 33m
When
Every day
Estimated price
$200 - $800
American Airlines
Website
aa.com
Flights from Boston to Chicago O'Hare
Ave. Duration
2h 41m
When
Every day
Estimated price
$24 - $140
Flights from Manchester to Chicago O'Hare
Ave. Duration
2h 45m
When
Every day
Estimated price
$45 - $250
Flights from Manchester to Chicago O'Hare via Philadelphia
Ave. Duration
5h 15m
When
Every day
Estimated price
$50 - $260
Flights from Manchester to Chicago O'Hare via Charlotte
Ave. Duration
5h 21m
When
Every day
Estimated price
$55 - $270
Flights from Manchester to Chicago O'Hare via Reagan Washington
Ave. Duration
5h 21m
When
Every day
Estimated price
$50 - $260
Flights from Providence to Chicago O'Hare
Ave. Duration
2h 36m
When
Every day
Estimated price
$80 - $420
Flights from Providence to Chicago O'Hare via Reagan Washington
Ave. Duration
4h 54m
When
Every day
Estimated price
$85 - $430
Flights from Providence to Chicago O'Hare via Philadelphia
Ave. Duration
4h 58m
When
Every day
Estimated price
$80 - $420
Delta
Website
delta.com
Flights from Boston to Chicago Midway via Detroit
Ave. Duration
4h 30m
When
Every day
Estimated price
$190 - $550
Flights from Boston to Chicago O'Hare
Ave. Duration
3h 1m
When
Every day
Estimated price
$100 - $300
Flights from Manchester to Chicago Midway via Detroit
Ave. Duration
4h 37m
When
Every day
Estimated price
$200 - $600
Flights from Manchester to Chicago O'Hare via Detroit
Ave. Duration
4h 38m
When
Every day
Estimated price
$100 - $300
Flights from Manchester to Chicago O'Hare via New York La Guardia
Ave. Duration
4h 50m
When
Monday to Friday
Estimated price
$110 - $330
Flights from Providence to Chicago Midway via Detroit
Ave. Duration
4h 13m
When
Every day
Estimated price
$340 - $950
Flights from Providence to Chicago O'Hare via Detroit
Ave. Duration
4h 33m
When
Every day
Estimated price
$180 - $500
United Airlines
Website
united.com
Flights from Boston to Chicago O'Hare
Ave. Duration
2h 48m
When
Every day
Estimated price
$65 - $290
Flights from Manchester to Chicago O'Hare via Washington Dulles
Ave. Duration
4h 45m
When
Every day
Estimated price
$85 - $330
Flights from Providence to Chicago O'Hare
Ave. Duration
2h 47m
When
Every day
Estimated price
$130 - $550
Flights from Providence to Chicago O'Hare via Washington Dulles
Ave. Duration
4h 47m
When
Every day
Estimated price
$140 - $550
JetBlue Airways
Website
jetblue.com
Flights from Boston to Chicago O'Hare
Ave. Duration
2h 55m
When
Every day
Estimated price
$35 - $290
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Boston South Station to Providence Amtrak Station
Ave. Duration
36 min
Frequency
Every 3 hours
Estimated price
$24 - $35
Website
amtrak.com
Coach Seat
$24 - $35
Premium
$180 - $250
Flexi Coach Seat
$30 - $50
Business Seat
$30 - $45
Train from Boston South Station to Chicago Union Station
Ave. Duration
22h
Frequency
Once daily
Estimated price
$100 - $150
Website
amtrak.com
Coach Seat
$100 - $150
Premium
$330 - $460
Flexi Coach Seat
$200 - $310
Business Seat
$220 - $310
Amtrak Northeast Regional

Amtrak’s Northeast Regional train service serves the US’ busy northeast corridor from Virginia to Massachusetts; major stops include Boston, Providence, New York City, Philadelphia, Washington DC and Baltimore. Amenities include Wi-Fi, a quiet car, cafe and business-class seating, and travelling with a small dog or cat is permitted. Book at least 14 days in advance for a cheaper Saver Fare.

Rome2rio's guide to Amtrak Northeast Regional
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Boston South Station to Providence Amtrak Station
Ave. Duration
49 min
Frequency
Every 3 hours
Estimated price
$35 - $70
Website
amtrak.com
Reserved Coach Seat
$35 - $70
Business Class Seat
$55 - $110
MBTA
Phone
617-222-3200
Website
mbta.com
Train from Boston / South Station Trains to Providence
Ave. Duration
1h 11m
Frequency
Hourly
Estimated price
$7 - $13
Website
MBTA
Bus operators
Boston Express
Phone
1800-639-8080
Email
contact@bostonexpressbus.com
Website
bostonexpressbus.com
Bus from Boston South Buses to North Londonderry, NH - exit 5
Ave. Duration
55 min
Frequency
Hourly
Estimated price
$12 - $19
Schedules at
bostonexpressbus.com
Book at
webstore.bostonexpressbus.com
Lucky Star Bus
Phone
(888) 881-0887 / (617) 269-5468
Email
info@luckystarbus.com
Website
luckystarbus.com
Bus from Boston South Buses to New York
Ave. Duration
5h
Frequency
Hourly
Estimated price
$30
Schedules at
luckystarbus.com
D&W Bus
Website
gotobus.com
Bus from New York to Chicago, IL
Ave. Duration
14h
Frequency
3 times a week
Estimated price
$90 - $120
Schedules at
gotobus.com
Book at
gotobus.com
Bus Ticket Inc.
Website
gotobus.com
Bus from New York, NY - Allen St. to Chicago, IL
Ave. Duration
15h
Frequency
3 times a week
Estimated price
$60 - $100
Book at
gotobus.com
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from South Station, Boston, MA to Port Authority Bus Terminal, New York, NY
Ave. Duration
4h 20m
Frequency
Every 3 hours
Estimated price
$35 - $50
Website
peterpanbus.com
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Boston South Buses to New York, Ny
Ave. Duration
6h 55m
Frequency
Hourly
Estimated price
$27 - $40
Website
greyhound.com
Economy
$27 - $40
Flexible
$50 - $70
Bus from New York, Ny to Chicago Amtrak, Il
Ave. Duration
18h 25m
Frequency
Once daily
Estimated price
$85 - $120
Website
greyhound.com
Economy
$85 - $120
Flexible
$130 - $190

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

More Questions & Answers

The quickest flight from Boston Airport to Chicago Midway Airport is the direct flight which takes 2h 35m.

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Boston to Chicago bus services, operated by Greyhound USA, arrive at Chicago Amtrak, Il station.

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Chicago is 1h behind Boston. It is currently 5:21 PM in Boston and 4:21 PM in Chicago.

Boston to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

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Yes, the driving distance between Boston to Chicago is 996 miles. It takes approximately 16h 32m to drive from Boston to Chicago.

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Delta and Southwest Airlines offer flights from Boston Airport to Chicago Midway Airport.

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Book your Boston to Chicago train tickets online with Omio.

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There are 664+ hotels available in Chicago. Prices start at $100 USD per night.

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The best way to get from Boston to Boston Airport is to bus which takes 0 min and costs $1 - $11.

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