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Stops
- Nonstopfrom $463
- Up to 1 stop$413
Airlines
- American Airlines$413
Cabin Class
- First$413
Departure Airports
- General Edward Lawrence Logan International Airport$413
Arrival Airports
- Chicago O Hare Airport$413
Layover Airports
- Charlotte Douglas International Airport$436
- Indianapolis International Airport$413
- New York John F Kennedy Airport$519
- Philadelphia International Airport$436
Best Price. GUARANTEED.
Exclusively for Priceline Members
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05/30/25
BOS
6h 30m
IND
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$413
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 30m
IND
05/30/25
ORD
06/06/25
ORD
2h 23m
Direct
06/06/25
BOS
$431
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 13m
PHL
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$436
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 41m
CLT
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$436
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 41m
CLT
05/30/25
ORD
06/06/25
ORD
2h 23m
Direct
06/06/25
BOS
$453
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 13m
PHL
05/30/25
ORD
06/06/25
ORD
2h 23m
Direct
06/06/25
BOS
$453
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 30m
IND
05/30/25
ORD
06/06/25
ORD
2h 26m
Direct
06/06/25
BOS
$453
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 30m
IND
05/30/25
ORD
06/06/25
ORD
2h 18m
Direct
06/06/25
BOS
$463
Free cancellation within 83 hours of booking
05/30/25
BOS
3h
Direct
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$463
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 14m
PHL
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$471
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 41m
CLT
05/30/25
ORD
06/06/25
ORD
2h 26m
Direct
06/06/25
BOS
$476
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 13m
PHL
05/30/25
ORD
06/06/25
ORD
2h 26m
Direct
06/06/25
BOS
$476
Free cancellation within 83 hours of booking
05/30/25
BOS
3h
Direct
05/30/25
ORD
06/06/25
ORD
2h 23m
Direct
06/06/25
BOS
$480
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 41m
CLT
05/30/25
ORD
06/06/25
ORD
2h 18m
Direct
06/06/25
BOS
$486
Free cancellation within 83 hours of booking
05/30/25
BOS
6h 13m
PHL
05/30/25
ORD
06/06/25
ORD
2h 18m
Direct
06/06/25
BOS
$486
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 14m
PHL
05/30/25
ORD
06/06/25
ORD
2h 23m
Direct
06/06/25
BOS
$488
Free cancellation within 83 hours of booking
05/30/25
BOS
3h
Direct
05/30/25
ORD
06/06/25
ORD
2h 26m
Direct
06/06/25
BOS
$503
Free cancellation within 83 hours of booking
05/30/25
BOS
3h 1m
Direct
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$509
Free cancellation within 83 hours of booking
05/30/25
BOS
2h 56m
Direct
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$509
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 14m
PHL
05/30/25
ORD
06/06/25
ORD
2h 26m
Direct
06/06/25
BOS
$511
Free cancellation within 83 hours of booking
05/30/25
BOS
3h
Direct
05/30/25
ORD
06/06/25
ORD
2h 18m
Direct
06/06/25
BOS
$513
Free cancellation within 83 hours of booking
05/30/25
BOS
4h 47m
PHL
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$519
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 14m
JFK
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$519
Free cancellation within 83 hours of booking
05/30/25
BOS
5h 29m
CLT
05/30/25
ORD
06/06/25
ORD
2h 40m
Direct
06/07/25
BOS
$519
Free cancellation within 83 hours of booking
05/30/25
BOS
2h 56m
Direct
05/30/25
ORD
06/06/25
ORD
2h 18m
Direct
06/06/25
BOS
$559
Free cancellation within 83 hours of booking
Top Deals on flights Business Class from Boston to Chicago
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
3h
Direct
May 29
ORD
as low as
$166
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
2h 56m
Direct
May 29
ORD
as low as
$224
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
4h 49m
IND
May 29
ORD
as low as
$240
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
4h 38m
CMH
May 29
ORD
as low as
$240
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
6h 20m
STL
May 29
ORD
as low as
$257
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
5h 29m
CLT
May 29
ORD
as low as
$298
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
7h 53m
IND
May 29
ORD
as low as
$312
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
4h 45m
PHL
May 29
ORD
as low as
$344
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
6h 41m
CLT
May 29
ORD
as low as
$344
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
7h 13m
LGA
May 29
ORD
as low as
$429
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
4h 47m
PHL
May 29
ORD
as low as
$429
Boston, US (BOS) - Chicago, US (CHI)
May 29
BOS
11h 21m
CMH
May 30
ORD
as low as
$457
Frequently Asked Questions
What are all possible destination arrival airports?
The possible destination arrival airport for your flight is Chicago O'Hare Airport.
What is the time difference between destination and arrival?
Boston is in the Eastern Time Zone and Chicago is in the Central Time Zone, so there is a 1-hour time difference, with Chicago being one hour behind Boston.
Is there a direct flight from Boston to Chicago?
Yes, there are several non-stop flights available from Boston to Chicago. Delta Air Lines offers a flight for $116, American Airlines for $116, JetBlue for $148, and United Airlines for $182.
Are there convenient layover flights from Boston to Chicago?
Yes, convenient 1 stop flights are available from Boston to Chicago with American Airlines at $183, JetBlue at $199, Spirit Airlines at $216, Delta Air Lines at $216, and United Airlines at $221. Additionally, there are 2 stop flights with Alaska Airlines at $729.
What are the most convenient layover airports for my flight?
For your flight from Boston to Chicago, convenient layover airports include Charlotte Douglas International Airport, New York John F Kennedy Airport, Fort Lauderdale Hollywood International Airport, Detroit Metropolitan Airport, and Washington Dulles Airport.
What is the cheapest and fastest flight from Boston to Chicago?
The cheapest flight is with Delta Air Lines at $116, 1h 53m. The fastest flight is with United Airlines at $186, 1h 50m.
Flights to Chicago
Return flights
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- North America
- United States
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Browse destinations
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- North America
- United States
- Illinois
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