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
Chicago
Boston
Outbound
04/21/25
1 Stopover (ATL)
F91442, F93512
06h 13min
Return
05/19/25
1 Stopover (ATL)
NK3381, NK1200
06h 53min
Frontier Airlines
$114
Best option
Chicago
Boston
Outbound
04/12/25
direct
AA3325
02h 28min
Return
04/27/25
direct
AA2837
02h 58min
American Airlines ?
$198
found yesterday
Chicago
Boston
Pay attention to transfer at connecting flight
Outbound
04/12/25
1 Stopover (FLL)
NK0002, NK0188
15h 43min
Return
04/27/25
2 Stopovers (ATL, LAX)
NK0217, NK0206, NK0491
33h 40min
Spirit Airlines
$151
found yesterday
Chicago
Boston
Outbound
04/21/25
1 Stopover (ATL)
F91442, F93512
06h 13min
Return
05/19/25
1 Stopover (ATL)
NK3381, NK1200
06h 53min
Frontier Airlines
$117
Chicago
Boston
Outbound
04/21/25
1 Stopover (MCO)
NK0573, NK0186
06h 41min
Return
05/19/25
1 Stopover (ATL)
NK3381, NK1200
06h 53min
Spirit Airlines
$119
Chicago
Boston
Outbound
04/21/25
1 Stopover (MCO)
NK0573, NK0186
06h 41min
Return
05/19/25
1 Stopover (ATL)
NK3381, NK1200
06h 53min
Spirit Airlines
$126
Chicago
Boston
Outbound
04/12/25
direct
B60612
02h 29min
Return
04/27/25
1 Stopover (MCO)
NK0997, NK0568
11h 33min
JetBlue Airways ?
$177
found yesterday
Chicago
Boston
Outbound
04/12/25
direct
UA1989
02h 32min
Return
04/27/25
direct
UA1414
02h 57min
United Airlines ?
$205
found yesterday
Chicago
Boston
Outbound
04/12/25
direct
UA1989
02h 32min
Return
04/27/25
direct
UA1414
02h 57min
United Airlines
$223
found yesterday
Chicago
Boston
Outbound
06/20/25
direct
B60312
02h 25min
Return
07/19/25
direct
B60311
02h 55min
JetBlue Airways ?
$234
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 $ 113,04
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 (ORD, MDW, RFD) (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