Flights from Chicago to Boston

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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
03/02/25
1 Stopover (EWR)
UA0563, UA1864
04h 05min
Return
03/07/25
direct
UA1414
03h 04min
United Airlines ?
$247
Best option
Chicago
Boston
Outbound
03/02/25
direct
AA3703
02h 20min
Return
03/07/25
direct
AA2837
02h 58min
American Airlines ?
$250
Chicago
Boston
Outbound
03/29/25
1 Stopover (JFK)
B60906, B61418
06h 32min
Return
04/02/25
direct
B60611
02h 56min
JetBlue Airways ?
$251
Chicago
Boston
Outbound
03/02/25
direct
AA3703
02h 20min
Return
03/07/25
direct
AA2837
02h 58min
American Airlines ?
$255
Chicago
Boston
Outbound
03/02/25
direct
AA3703
02h 20min
Return
03/07/25
direct
AA2837
02h 58min
American Airlines ?
$319
Chicago
Boston
Outbound
03/02/25
1 Stopover (EWR)
UA0563, UA1864
04h 05min
Return
03/07/25
1 Stopover (EWR)
UA0570, UA1875
06h 41min
United Airlines
$348
Chicago
Boston
Outbound
03/29/25
1 Stopover (DTW)
DL3858, DL1171
05h 27min
Return
04/02/25
1 Stopover (DTW)
DL2222, DL3869
06h 08min
Delta Air Lines ?
$383
Chicago
Boston
Outbound
03/29/25
1 Stopover (ATL)
F92292, F93512
07h 04min
Return
04/02/25
1 Stopover (RDU)
F93057, F93717
13h 39min
Frontier Airlines
$401
Chicago
Boston
Outbound
03/29/25
1 Stopover (ATL)
F92292, F93512
07h 04min
Return
04/02/25
1 Stopover (RDU)
F93057, F93717
13h 39min
Frontier Airlines
$411
Chicago
Boston
Outbound
03/02/25
1 Stopover (MCO)
NK0507, NK1848
13h 49min
Return
03/07/25
1 Stopover (FLL)
NK2887, NK0003
09h 31min
Spirit Airlines
$458
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 $ 246,24
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
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.