Flight Routes from Chicago to Boston

Trip type

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
06/25/26
direct
B60312
02h 27min
Return
06/30/26
direct
B60811
03h 05min
JetBlue Airways ?
$212
Chicago
Boston
Outbound
06/25/26
1 Stopover (ATL)
F92198, F93086
06h 30min
Return
06/30/26
1 Stopover (ATL)
F93085, F91441
07h 29min
Frontier Airlines
$504
Chicago
Boston
Outbound
06/25/26
1 Stopover (ATL)
F91596, F93086
16h 32min
Return
06/30/26
1 Stopover (ATL)
F93085, F93397
17h 37min
Frontier Airlines ?
$520
Chicago
Boston
Outbound
06/25/26
1 Stopover (IAD)
UA2437, UA0755
07h 06min
Return
06/30/26
direct
UA2631
02h 58min
United Airlines
$612
Chicago
Boston
Outbound
06/25/26
direct
AA2303
02h 36min
Return
06/30/26
direct
AA1554
03h 24min
American Airlines ?
$712
Chicago
Boston
Outbound
06/25/26
1 Stopover (MSP)
SY0262, SY0251
12h 54min
Return
06/30/26
1 Stopover (MCO)
NK2091, NK0393
12h 47min
Sun Country Airlines
$717
Chicago
Boston
Outbound
06/25/26
1 Stopover (MSP)
SY0262, SY0251
12h 54min
Return
06/30/26
1 Stopover (MCO)
NK2091, NK0393
12h 47min
Sun Country Airlines
$730
Chicago
Boston
Outbound
06/25/26
1 Stopover (MSP)
DL1306, DL2614
05h 32min
Return
06/30/26
direct
DL2570
02h 58min
Delta Air Lines ?
$2,987
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 $ 211,80
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