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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

Fly Boston to Chicago Midway

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

Cheapest

Fly Boston to Chicago O'Hare

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

Bus to Manchester, fly to Chicago Midway

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

Bus to Manchester, fly to Chicago O'Hare

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

Train to Providence, fly to Chicago Midway

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

Train to Providence, fly to Chicago O'Hare

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

Fly Boston to Milwaukee, train

  1. Fly from Boston (BOS) to Milwaukee (MKE)
  2. Take the train from Milwaukee to Chicago Union Station

Bus

  1. Take the bus from Boston, MA Oak & Harrison to New York, NY
  2. Take the bus from New York, NY - 3 Allen St to Chicago

Train

  1. Take the train from Boston to Chicago Union Station

Drive

  1. Drive from Boston to Chicago
Boston → Chicago
Fully open

Travel safe during COVID-19

Rules to follow in United States

2m

Recommended

Recommended

Travel within United States

Domestic border crossings may be subject to approval, testing and quarantine

COVID-19 help in United States

If you need help, visit the national COVID-19 website or call the COVID-19 Helpline 800-232-4636

Frequently Asked Questions


Yes, travel within United States is currently allowed.

Explore travel options

Domestic travel is not restricted, but some conditions may apply

  • Face masks are recommended
  • There is a social distancing requirement of 2 metres
  • Domestic border crossings may be subject to approval, testing and quarantine

Explore travel options

The national COVID-19 helpline number in Chicago is 800-232-4636.

Wearing a face mask on public transport in Chicago is recommended.

The social distance requirement in Chicago is 2 metres.

Make yourself known to an official member of staff and/or call the national coronavirus helpline number on 800-232-4636.

Last updated: 14 Sep 2021
Exceptions may apply, for full details: Centers for Disease control and prevention (CDC).

We're working around the clock to bring you the latest COVID-19 travel updates.
This information is compiled from official sources. To the best of our knowledge, it is correct as of the last update.
Visit Rome2rio travel advice for general help.

Questions & Answers

The cheapest way to get from Boston to Chicago is to fly which costs $50 - $210 and takes 4h 33m.

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The quickest way to get from Boston to Chicago is to fly which costs $150 - $800 and takes 4h 20m.

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No, there is no direct bus from Boston to Chicago. However, there are services departing from Boston, MA Oak & Harrison and arriving at Chicago via New York, NY - 3 Allen St. The journey, including transfers, takes approximately 20h 10m.

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

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It is 853 miles from Boston to Chicago. It is approximately 995.4 miles to drive.

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The best way to get from Boston to Chicago without a car is to bus which takes 20h 10m and costs $55 - $120.

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It takes approximately 4h 20m to get from Boston to Chicago, including transfers.

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Boston to Chicago bus services, operated by Coach Run, depart from Boston, MA Oak & Harrison station.

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

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The best way to get from Boston to Chicago is to fly which takes 4h 20m and costs $150 - $800. Alternatively, you can bus, which costs $55 - $120 and takes 20h 10m, 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 20m

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

Southwest Airlines, Delta and Allegiant Air fly from Boston to Chicago hourly. Alternatively, you can take a bus from Boston to Chicago via New York, NY and New York, NY - 3 Allen St in around 20h 10m.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Boston to Chicago Midway
Ave. Duration
2h 48m
When
Every day
Estimated price
$100 - $650
Flights from Boston to Chicago Midway via Baltimore
Ave. Duration
4h 30m
When
Sunday
Estimated price
$100 - $650
Flights from Manchester to Chicago Midway
Ave. Duration
2h 36m
When
Every day
Estimated price
$210 - $650
Flights from Manchester to Chicago Midway via Baltimore
Ave. Duration
5h 8m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $700
Flights from Manchester to Chicago O'Hare via Baltimore
Ave. Duration
5h 28m
When
Monday, Thursday, Friday, Saturday and Sunday
Estimated price
$150 - $470
Flights from Providence to Chicago Midway
Ave. Duration
2h 38m
When
Every day
Estimated price
$230 - $750
Flights from Providence to Chicago Midway via Baltimore
Ave. Duration
5h 19m
When
Every day
Estimated price
$230 - $750
Flights from Providence to Chicago O'Hare via Baltimore
Ave. Duration
4h 30m
When
Monday, Thursday and Friday
Estimated price
$160 - $500
Flights from Boston to Milwaukee via Baltimore
Ave. Duration
5h 5m
When
Tuesday and Wednesday
Estimated price
$130 - $440
American Airlines
Website
aa.com
Flights from Boston to Chicago O'Hare
Ave. Duration
3h 2m
When
Every day
Estimated price
$80 - $480
Flights from Manchester to Chicago O'Hare
Ave. Duration
2h 51m
When
Every day
Estimated price
$220 - $550
Flights from Manchester to Chicago O'Hare via Philadelphia
Ave. Duration
5h 25m
When
Every day
Estimated price
$220 - $550
Flights from Manchester to Chicago O'Hare via Charlotte
Ave. Duration
5h 56m
When
Every day
Estimated price
$220 - $550
Flights from Manchester to Chicago O'Hare via Reagan Washington
Ave. Duration
6h 39m
When
Saturday
Estimated price
$220 - $550
Flights from Providence to Chicago O'Hare
Ave. Duration
2h 51m
When
Every day
Estimated price
$220 - $490
Flights from Providence to Chicago O'Hare via Philadelphia
Ave. Duration
5h 7m
When
Every day
Estimated price
$220 - $490
Flights from Boston to Milwaukee via Chicago O'Hare
Ave. Duration
4h 59m
When
Wednesday and Sunday
Estimated price
$170 - $650
Flights from Boston to Milwaukee via Philadelphia
Ave. Duration
5h 4m
When
Sunday
Estimated price
$170 - $650
Delta
Website
delta.com
Flights from Boston to Chicago Midway via Detroit
Ave. Duration
4h 20m
When
Every day
Estimated price
$350 - $450
Flights from Boston to Chicago O'Hare
Ave. Duration
2h 51m
When
Every day
Estimated price
$240 - $310
Flights from Boston to Chicago O'Hare via Detroit
Ave. Duration
4h 27m
When
Every day
Estimated price
$240 - $310
Flights from Providence to Chicago Midway via Detroit
Ave. Duration
4h 32m
When
Every day
Estimated price
$500 - $650
Flights from Providence to Chicago Midway via Atlanta
Ave. Duration
5h 55m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$550 - $800
Flights from Providence to Chicago O'Hare via Detroit
Ave. Duration
4h 30m
When
Every day
Estimated price
$350 - $450
Flights from Boston to Milwaukee
Ave. Duration
2h 35m
When
Every day
Estimated price
$300 - $390
Flights from Boston to Milwaukee via Detroit
Ave. Duration
4h 23m
When
Every day
Estimated price
$300 - $390
Flights from Boston to Milwaukee via New York La Guardia
Ave. Duration
5h
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$300 - $390
United Airlines
Website
united.com
Flights from Boston to Chicago O'Hare
Ave. Duration
2h 54m
When
Every day
Estimated price
$110 - $480
Flights from Manchester to Chicago O'Hare via Washington Dulles
Ave. Duration
5h 24m
When
Every day
Estimated price
$240 - $600
Flights from Manchester to Chicago O'Hare via Newark
Ave. Duration
5h 43m
When
Every day
Estimated price
$240 - $600
Flights from Providence to Chicago O'Hare
Ave. Duration
2h 54m
When
Every day
Estimated price
$230 - $600
Flights from Providence to Chicago O'Hare via Washington Dulles
Ave. Duration
4h 52m
When
Every day
Estimated price
$230 - $600
Flights from Boston to Milwaukee via Chicago O'Hare
Ave. Duration
4h 44m
When
Every day
Estimated price
$180 - $800
JetBlue Airways
Website
jetblue.com
Flights from Boston to Chicago O'Hare
Ave. Duration
3h 3m
When
Every day
Estimated price
$80 - $470
Flights from Boston to Milwaukee
Ave. Duration
2h 40m
When
Every day
Estimated price
$110 - $460
Flights from Boston to Milwaukee via New York JFK
Ave. Duration
5h 3m
When
Every day
Estimated price
$110 - $460
Allegiant Air
Website
allegiantair.com
Flights from Boston to Chicago Midway via Knoxville
Ave. Duration
4h 35m
When
Thursday and Sunday
Estimated price
$180 - $490
Train operators
Amtrak Acela Express

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 Acela Express
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Boston to Providence
Ave. Duration
34 min
Frequency
Every 3 hours
Estimated price
$70 - $110
Schedules at
amtrak.com
Business Seat - Adult
$75 - $110
Business Seat - Seniors and Active Military
$75 - $110
Business Seat - Child
$70 - $110
First Class - Adult
$120 - $180
First Class - Senior Citizens and Active Military
$120 - $180
First Class - Child
$120 - $170
MBTA
Phone
617-222-3200
Website
mbta.com
Train from South Station to Providence
Ave. Duration
1h 8m
Frequency
Hourly
Estimated price
$0 - $13
Website
MBTA
children 11 and under
$0
Adult
$11 - $13
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 to Providence
Ave. Duration
49 min
Frequency
Every 3 hours
Estimated price
$13 - $75
Schedules at
amtrak.com
Child 2-12 with paid adult
$13 - $40
Reserved Coach Seat
$25 - $75
Business Class Seat
$40 - $100
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 Milwaukee to Chicago Union Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$27 - $40
Schedules at
amtrak.com
Coach Seat
$27 - $40
Premium
$180 - $260
Flexi Coach Seat
$40 - $60
Business Seat
$35 - $55
Train from Boston to Chicago Union Station
Ave. Duration
22h
Frequency
Twice daily
Estimated price
$100 - $150
Schedules at
amtrak.com
Coach Seat
$100 - $150
Premium
$330 - $460
Flexi Coach Seat
$200 - $310
Business Seat
$220 - $310
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
Every 2 hours
Estimated price
$12 - $19
Schedules at
bostonexpressbus.com
Book at
webstore.bostonexpressbus.com
Coach Run
Website
coachrun.com
Bus from Boston, MA Oak & Harrison to New York, NY
Ave. Duration
4h 10m
Frequency
3 times a day
Estimated price
$9 - $20
Schedules at
coachrun.com
Book at
gotobus.com
Wanda Coach
Phone
646-630-7186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from New York, NY - 3 Allen St to Chicago
Ave. Duration
15h
Frequency
3 times a week
Estimated price
$50 - $100
Book at
GoTo Bus

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 45m.

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Boston to Chicago bus services, operated by Wanda Coach, arrive at Chicago station.

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Chicago is 1h behind Boston. It is currently 8:19 AM in Boston and 7:19 AM 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 995 miles. It takes approximately 16h 30m to drive from Boston to Chicago.

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Allegiant Air, 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 310+ 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 - $13.

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