There are 10 ways to get from Chicago to Boston 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 Chicago Midway to Boston  •  3 h 56 min

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

$94 - $390

Cheapest option

Fly Chicago O'Hare to Boston  •  4 h 12 min

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

$79 - $271

8 alternative options

Fly Chicago Midway to Manchester, bus  •  5 h 6 min

  1. Fly from Chicago Midway (MDW) to Manchester (MHT) MDW - MHT
  2. Take the bus from Manchester Arpt to Boston, Ma

$159 - $500

Fly Chicago O'Hare to Manchester, bus  •  5 h 42 min

  1. Fly from Chicago O'Hare (ORD) to Manchester (MHT) ORD - MHT
  2. Take the bus from Manchester Arpt to Boston, Ma

$209 - $501

Fly Chicago Midway to Providence, train  •  6 h 7 min

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

$111 - $496

Fly Chicago O'Hare to Providence, train  •  6 h 32 min

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

$111 - $647

Bus D&J Bus  •  19 h 30 min

  1. Take the bus from Chicago, IL to New York Djb149 / ...
  2. Take the bus from New York to Boston, MA New York

$115 - $125

Train  •  21 h 31 min

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

$130 - $390

Bus Greyhound USA  •  22 h 12 min

  1. Take the bus from Chicago, Il to New York, Ny 1604
  2. Take the bus from New York, Ny to Boston, Ma 2504 / ...

$101 - $262

Drive  •  16 h 31 min

  1. Drive from Chicago to Boston 996.8 miles

$95 - $150

Questions & Answers

The cheapest way to get from Chicago to Boston is to drive which costs $95 - $150 and takes 16 h 31 min.

More details

The quickest way to get from Chicago to Boston is to fly which costs $90 - $390 and takes 3 h 56 min.

More details

The distance between Chicago and Boston is 853 miles. The road distance is 996.8 miles.

Get driving directions

It takes approximately 3 h 56 min to get from Chicago to Boston, including transfers.

More details

No, there is no direct bus from Chicago to Boston. However, there are services departing from Chicago, IL and arriving at Boston, MA via New York. The journey, including transfers, takes approximately 19 h 30 min.

More details

Yes, there is a direct train departing from Chicago Union Station Amtrak station and arriving at Boston South Station Amtrak station. Services depart once daily, and operate every day. The journey takes approximately 21 h 31 min.

More details

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

Southwest Airlines, Delta and Porter Airlines fly from Chicago to Boston hourly. Alternatively, you can take a bus from Chicago to Boston via New York in around 19 h 30 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Boston
Ave. Duration
2 h 14 min
When
Every day
Estimated price
$130 - $550
Flights from Chicago Midway to Manchester
Ave. Duration
2 h 5 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Manchester via Baltimore
Ave. Duration
4 h 25 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Providence
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$140 - $700
Flights from Chicago Midway to Providence via Baltimore
Ave. Duration
4 h 8 min
When
Every day
Estimated price
$140 - $700
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 17 min
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to Manchester via Philadelphia
Ave. Duration
4 h 57 min
When
Every day
Estimated price
$340 - $750
Flights from Chicago O'Hare to Manchester via Charlotte
Ave. Duration
5 h 4 min
When
Every day
Estimated price
$340 - $750
Flights from Chicago O'Hare to Manchester via Reagan Washington
Ave. Duration
5 h 19 min
When
Saturday
Estimated price
$340 - $750
Flights from Chicago O'Hare to Providence
Ave. Duration
2 h 21 min
When
Every day
Estimated price
$180 - $650
Flights from Chicago O'Hare to Providence via Philadelphia
Ave. Duration
4 h 15 min
When
Every day
Estimated price
$180 - $650
Flights from Chicago O'Hare to Providence via Reagan Washington
Ave. Duration
4 h 8 min
When
Monday to Saturday
Estimated price
$180 - $650
United Airlines
Website
united.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 19 min
When
Every day
Estimated price
$130 - $650
Flights from Chicago O'Hare to Manchester
Ave. Duration
2 h 23 min
When
Every day
Estimated price
$320 - $800
Flights from Chicago O'Hare to Providence
Ave. Duration
2 h 28 min
When
Every day
Estimated price
$170 - $650
Flights from Chicago O'Hare to Providence via Washington Dulles
Ave. Duration
4 h 2 min
When
Every day
Estimated price
$170 - $650
Delta
Website
delta.com
Flights from Chicago Midway to Boston via Detroit
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$140 - $850
Flights from Chicago Midway to Manchester via Detroit
Ave. Duration
4 h 13 min
When
Every day
Estimated price
$180 - $850
Flights from Chicago O'Hare to Manchester via Detroit
Ave. Duration
4 h 49 min
When
Every day
Estimated price
$390 - $900
Flights from Chicago O'Hare to Manchester via New York La Guardia
Ave. Duration
4 h 36 min
When
Every day
Estimated price
$390 - $900
Flights from Chicago Midway to Providence via Detroit
Ave. Duration
4 h 13 min
When
Every day
Estimated price
$140 - $650
Flights from Chicago O'Hare to Providence via Detroit
Ave. Duration
4 h 11 min
When
Every day
Estimated price
$180 - $600
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$140 - $600
Air Canada
Website
aircanada.com
Flights from Chicago O'Hare to Manchester
Ave. Duration
2 h 24 min
When
Every day
Estimated price
$320 - $800
Flights from Chicago O'Hare to Providence
Ave. Duration
2 h 28 min
When
Every day
Estimated price
$170 - $650
Flights from Chicago O'Hare to Providence via Toronto
Ave. Duration
4 h 9 min
When
Every day
Estimated price
$180 - $700
Porter Airlines
Website
flyporter.com
Flights from Chicago Midway to Boston via Toronto Island
Ave. Duration
4 h 10 min
When
Sunday
Estimated price
$220 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 27 min
When
Every day
Estimated price
$110 - $450
Train operators
Amtrak Acela Express
Rome2rio's guide to Amtrak Acela Express
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Providence Amtrak to Boston South Station Amtrak
Ave. Duration
59 min
Frequency
Hourly
Estimated price
$60 - $160
Website
amtrak.com
Business Seat
$60 - $150
First Class Seat
$120 - $160
Amtrak
Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak to Boston South Station Amtrak
Ave. Duration
21 h 31 min
Frequency
Once daily
Estimated price
$130 - $390
Website
amtrak.com
Coach Seat
$130 - $200
Flexi Coach Seat
$240 - $340
Business Coach Seat
$280 - $390
Room
$500 - $750
Bus operators
Greyhound USA
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 Manchester Arpt to Boston, Ma
Ave. Duration
1 h
Frequency
Hourly
Estimated price
$12 - $26
Website
greyhound.com
Economy
$12 - $17
Flexible
$20 - $26
Bus from Chicago, Il to New York, Ny
Ave. Duration
17 h 40 min
Frequency
Hourly
Estimated price
$80 - $200
Website
greyhound.com
Economy
$80 - $130
Flexible
$150 - $200
Bus from New York, Ny to Boston, Ma
Ave. Duration
4 h 20 min
Frequency
Every 30 minutes
Estimated price
$25 - $65
Website
greyhound.com
Economy
$25 - $40
Flexible
$45 - $65
D&J Bus
Bus from Chicago, IL to New York
Ave. Duration
14 h
Frequency
Once daily
Estimated price
$90
Schedules at
gotobus.com
Book at
gotobus.com
Wanda Coach
Phone
6466307186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from Chicago to New York, NY
Ave. Duration
13 h
Frequency
3 times a week
Estimated price
$100
Schedules at
wandacoach.com
Lucky Star Bus
Phone
(888) 881-0887 / (617) 269-5468
Email
info@luckystarbus.com
Website
luckystarbus.com
Bus from New York to Boston, MA
Ave. Duration
4 h 30 min
Frequency
Every 2 hours
Estimated price
$25
Schedules at
luckystarbus.com
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from New York City, NY - Port Authority Bus Terminal to Boston, MA - South Station
Ave. Duration
4 h 15 min
Frequency
Hourly
Estimated price
$21 - $40
Schedules at
peterpanbus.com
Book at
webstore.peterpanbus.com

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