Flights from Chicago to Boston

Our cheapest offers for flights from Chicago to Boston

Here you can compare cheap flights from Chicago (CHI) to Boston (BOS) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Boston. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Chicago
Boston
Outbound
02/13/26
direct
AA1033
02h 24min
Return
02/26/26
direct
B60811
02h 52min
American Airlines ?
$143
Chicago
Boston
Outbound
02/13/26
direct
UA1989
02h 28min
Return
02/26/26
direct
UA0398
03h 05min
United Airlines ?
$211
Chicago
Boston
Outbound
02/13/26
direct
B61012
02h 25min
Return
02/26/26
direct
B60811
02h 52min
JetBlue Airways ?
$217
Chicago
Boston
Outbound
02/13/26
direct
UA1989
02h 28min
Return
02/26/26
direct
UA1414
03h 05min
United Airlines ?
$235
Chicago
Boston
Outbound
02/13/26
direct
AA1033
02h 24min
Return
02/26/26
direct
AA3477
03h 01min
American Airlines ?
$283
Chicago
Boston
Outbound
04/03/26
direct
UA1693
02h 33min
Return
04/16/26
direct
UA1921
02h 44min
United Airlines ?
$311
Chicago
Boston
Outbound
02/13/26
1 Stopover (FLL)
NK0002, NK3061
12h 06min
Return
02/26/26
1 Stopover (FLL)
NK1097, NK1986
12h 35min
Spirit Airlines
$361
Chicago
Boston
Outbound
02/13/26
1 Stopover (FLL)
NK0002, NK3061
12h 06min
Return
02/26/26
1 Stopover (FLL)
NK1097, NK1986
12h 35min
Spirit Airlines
$379
Chicago
Boston
Outbound
04/03/26
1 Stopover (ATL)
F91442, F93086
12h 25min
Return
04/16/26
1 Stopover (MSP)
SY0252, SY0261
08h 04min
Frontier Airlines ?
$436
Chicago
Boston
Outbound
04/03/26
direct
AA4650
02h 31min
Return
04/16/26
1 Stopover (CVG)
AA4760, AA3554
05h 10min
American Airlines ?
$486
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Boston

Favorite airline: Spirit Airlines
Flight tickets on the route Chicago – Boston are most frequently booked with Spirit Airlines.
Spirit Airlines
33 %
United Airlines
20 %
Delta
15 %
Direct flights are more expensive
On this route, direct flights are $13.00 more expensive than flights with a stopover.
non stop flight
1 stop
02h 30min
09h 23min
$160
$147
The favorite connection is non-stop
Flights from Chicago to Boston are most often booked as a direct flight.
Route
bookings
Direct flights
02h 30min, from $160
44 %
1 stopover Orlando International Airport, FL
09h 23min, from $147
15 %
1 stopover Minneapolis - St. Paul International Airport, MN
13h 44min, from $335
12 %

Important flight information

Flight information: Chicago - Boston

Roundtrip from $142.61
Flight duration min. 02:08 / max. 11:15
Return flight duration min. 02:45/ max. 06:55
Distance 1371 km
Flights per week 153
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Boston Logan International Airport, MA (BOS)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Boston
Flight destinations with a similar price
Flight destinations with a similar price