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  •  4 h 28 min

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

$94 - $404

Cheapest option

Fly Boston to Chicago O'Hare  •  4 h 49 min

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

$79 - $285

8 alternative options

Bus to Manchester, fly to Chicago Midway  •  5 h 22 min

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

$124 - $449

Train to Providence, fly to Chicago Midway  •  5 h 45 min

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

$118 - $350

Bus to Hartford, fly to Chicago Midway  •  6 h 48 min

  1. Take the bus from Boston, MA - South Station to Hartford, CT - Union Station
  2. Fly from Hartford (BDL) to Chicago Midway (MDW) BDL - MDW

$189 - $454

Bus to Manchester, fly to Chicago O'Hare  •  6 h 2 min

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

$174 - $450

Train to Providence, fly to Chicago O'Hare  •  6 h 21 min

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

$118 - $501

Bus  •  20 h

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

$100 - $215

Train  •  21 h 55 min

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

$130 - $390

Drive  •  16 h 26 min

  1. Drive from Boston to Chicago 996.4 miles

$95 - $150

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 20 h.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Boston to Chicago Midway
Avg. Duration
2 h 50 min
When
Every day
Estimated price
$130 - $550
Flights from Boston to Chicago Midway via Baltimore
Avg. Duration
5 h 5 min
When
Monday to Friday
Estimated price
$130 - $550
Flights from Manchester to Chicago Midway
Avg. Duration
2 h 36 min
When
Every day
Estimated price
$120 - $900
Flights from Manchester to Chicago Midway via Baltimore
Avg. Duration
5 h 8 min
When
Every day
Estimated price
$120 - $900
Flights from Providence to Chicago Midway
Avg. Duration
2 h 37 min
When
Every day
Estimated price
$140 - $700
Flights from Providence to Chicago Midway via Baltimore
Avg. Duration
5 h 10 min
When
Every day
Estimated price
$140 - $700
Flights from Providence to Chicago Midway via Reagan Washington
Avg. Duration
4 h 30 min
When
Saturday
Estimated price
$140 - $700
Flights from Hartford to Chicago Midway
Avg. Duration
2 h 33 min
When
Every day
Estimated price
$190 - $900
Flights from Hartford to Chicago Midway via Baltimore
Avg. Duration
4 h 35 min
When
Every day
Estimated price
$190 - $900
American Airlines
Website
aa.com
Flights from Boston to Chicago O'Hare
Avg. Duration
2 h 59 min
When
Every day
Estimated price
$120 - $490
Flights from Manchester to Chicago O'Hare via Philadelphia
Avg. Duration
5 h 33 min
When
Every day
Estimated price
$340 - $750
Flights from Manchester to Chicago O'Hare via Reagan Washington
Avg. Duration
5 h 47 min
When
Every day
Estimated price
$340 - $750
Flights from Manchester to Chicago O'Hare via Charlotte
Avg. Duration
5 h 57 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$340 - $750
Flights from Providence to Chicago O'Hare
Avg. Duration
2 h 56 min
When
Every day
Estimated price
$180 - $650
Flights from Providence to Chicago O'Hare via Philadelphia
Avg. Duration
5 h 20 min
When
Every day
Estimated price
$180 - $650
Flights from Providence to Chicago O'Hare via Reagan Washington
Avg. Duration
5 h 18 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$180 - $650
Delta
Website
delta.com
Flights from Boston to Chicago Midway via Detroit
Avg. Duration
4 h 54 min
When
Every day
Estimated price
$140 - $850
Flights from Manchester to Chicago Midway via Detroit
Avg. Duration
5 h 1 min
When
Monday, Thursday, Friday, Saturday and Sunday
Estimated price
$180 - $850
Flights from Providence to Chicago Midway via Detroit
Avg. Duration
4 h 50 min
When
Every day
Estimated price
$140 - $650
Flights from Hartford to Chicago Midway via Detroit
Avg. Duration
5 h 2 min
When
Saturday
Estimated price
$200 - $750
Flights from Hartford to Chicago Midway via Minneapolis
Avg. Duration
5 h 55 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$200 - $750
Flights from Manchester to Chicago O'Hare via Detroit
Avg. Duration
4 h 54 min
When
Every day
Estimated price
$390 - $900
Flights from Manchester to Chicago O'Hare via New York La Guardia
Avg. Duration
5 h 40 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $900
Flights from Providence to Chicago O'Hare via Detroit
Avg. Duration
4 h 42 min
When
Every day
Estimated price
$180 - $600
United Airlines
Website
united.com
Flights from Boston to Chicago O'Hare
Avg. Duration
2 h 55 min
When
Every day
Estimated price
$130 - $650
Flights from Manchester to Chicago O'Hare
Avg. Duration
2 h 57 min
When
Every day
Estimated price
$320 - $800
Flights from Manchester to Chicago O'Hare via Newark
Avg. Duration
5 h 47 min
When
Every day
Estimated price
$320 - $800
Flights from Providence to Chicago O'Hare
Avg. Duration
3 h 2 min
When
Every day
Estimated price
$170 - $650
Flights from Providence to Chicago O'Hare via Washington Dulles
Avg. Duration
5 h 10 min
When
Every day
Estimated price
$170 - $650
Flights from Providence to Chicago O'Hare via Newark
Avg. Duration
5 h 9 min
When
Every day
Estimated price
$170 - $650
JetBlue Airways
Website
jetblue.com
Flights from Boston to Chicago O'Hare
Avg. Duration
2 h 59 min
When
Every day
Estimated price
$140 - $600
Air Canada
Website
aircanada.com
Flights from Boston to Chicago O'Hare via Toronto
Avg. Duration
4 h 47 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$140 - $600
Flights from Manchester to Chicago O'Hare
Avg. Duration
2 h 57 min
When
Every day
Estimated price
$320 - $800
Flights from Providence to Chicago O'Hare via Toronto
Avg. Duration
4 h 32 min
When
Every day
Estimated price
$170 - $650
Porter Airlines
Website
flyporter.com
Flights from Boston to Chicago Midway via Toronto Island
Avg. Duration
4 h 57 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Boston to Chicago O'Hare
Avg. Duration
2 h 48 min
When
Every day
Estimated price
$110 - $450
Train operators
Amtrak Acela Express
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Boston South Station Amtrak to Providence Amtrak
Avg. Duration
36 min
Frequency
Hourly
Estimated price
$14
Website
amtrak.com
Rome2rio guide to
rome2rio.com
Coach
$14
Business Class
$29 - $60
First Class
$65 - $95
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Boston South Station Amtrak to Chicago Union Station Amtrak
Avg. Duration
21 h 55 min
Frequency
Once daily
Estimated price
$130 - $390
Website
amtrak.com
Rome2rio guide to
rome2rio.com
Coach Seat
$130 - $200
Flexi Coach Seat
$240 - $340
Business Coach Seat
$280 - $390
Room
$500 - $750
Bus operators
Greyhound USA
Phone
+1 214-849-8100
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Boston, MA to Manchester Arpt, NH
Avg. Duration
1 h 19 min
Frequency
Once daily
Estimated price
$11 - $26
Website
greyhound.com
Rome2rio guide to
rome2rio.com
Economy
$11 - $17
Flexible
$20 - $26
Bus from Boston, MA to Hartford, CT
Avg. Duration
1 h 50 min
Frequency
Once daily
Estimated price
$16 - $40
Website
greyhound.com
Rome2rio guide to
rome2rio.com
Economy
$16 - $24
Flexible
$29 - $40
Bus from New York to Chicago, IL
Avg. Duration
14 h 30 min
Frequency
Every 4 hours
Estimated price
$75 - $190
Website
greyhound.com
Rome2rio guide to
rome2rio.com
Economy
$75 - $130
Flexible
$140 - $190
Peter Pan Bus Lines
Phone
1-800-343-9999
Email
dveronesi@peterpanbus.com
Website
peterpanbus.com
Bus from Boston, MA - South Station to Hartford, CT - Union Station
Avg. Duration
1 h 55 min
Frequency
Every 5 minutes
Estimated price
$15 - $28
Website
peterpanbus.com
Lucky Star Bus
Phone
(888) 881-0887 / (617) 269-5468
Email
info@luckystarbus.com
Website
luckystarbus.com
Bus from Boston, MA to New York
Avg. Duration
4 h 30 min
Frequency
Hourly
Estimated price
$25
Schedules at
luckystarbus.com
D&J Bus
Bus from New York to Chicago, IL
Avg. Duration
14 h
Frequency
Once daily
Estimated price
$90
Schedules at
gotobus.com
Book at
gotobus.com

Want to know more about travelling around United States

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Questions & Answers

How far is it from Boston to Chicago?

The distance between Boston and Chicago is 1365 km. The road distance is 1594 km.

What is the cheapest way to get from Boston to Chicago?

The cheapest way to get from Boston to Chicago is to bus which costs $120 and takes 20 h.

What is the fastest way to get from Boston to Chicago?

The quickest way to get from Boston to Chicago is to fly which takes 4 h 28 min and costs $180.

Is there a direct train between Boston and Chicago?

Yes, there is a direct train departing from Boston South Station Amtrak and arriving at Chicago Union Station Amtrak. Services depart once daily, and operate every day. The journey takes approximately 21 h 55 min.

Is there a direct bus between Boston and Chicago?

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

How long does it take to get from Boston to Chicago?

It takes approximately 4 h 28 min to get from Boston to Chicago, including transfers.