$146
Cheap
$86
$86
Expensive
$293
$293
Favorite airline: United Airlines
The most popular airline for flights from Boston to Chicago is United Airlines.
United Airlines
19 %
American Airlines
17 %
JetBlue Airways
14 %
Tip: book 5 days before departure
Save up to 63 % by booking flights 5 days before departure.
Cheapest weekday: Thursday
Compared to other weekdays, flights are cheapest on Thursday.
Direct flights are cheaper
Direct flights on this route are $ 7.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 41min
05h 13min
$146
$153
The favorite connection is non-stop
65 % of all bookings on the route Boston to Chicago are for non-stop flights.
Route
bookings
Direct flights
02h 41min, from $146
65 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
04h 28min, from $169
11 %
1 stopover New York - La Guardia Airport, NY
06h 53min, from $159
7 %
Round trip from $146.00
Flights on this route with a departure on 08/22/2019 and return flight on 08/31/2019 currently cost $146.00.
Flights from Boston to Chicago
Outbound flight: 08/22/19
06:00 BOS
07:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 08/31/19
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $146
78 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $149
12 days ago*
Outbound flight: 12/30/19
06:00 BOS
07:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/01/20
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
12 days ago*
Outbound flight: 12/30/19
20:25 BOS
22:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/02/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
06:00 CHI
09:10 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $149
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
06:00 CHI
09:10 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $149
12 days ago*
Outbound flight: 12/30/19
08:00 BOS
09:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/01/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
12 days ago*
Outbound flight: 12/30/19
20:25 BOS
22:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/02/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $149
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Interjet Return flight: 01/01/20
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Interjet $150
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Interjet Return flight: 01/02/20
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Interjet $150
12 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Interjet Return flight: 01/02/20
06:00 CHI
09:16 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Interjet $150
12 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/02/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:50 BOS
21:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
06:00 CHI
09:10 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/01/20
12:00 CHI
15:17 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/01/20
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/02/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/01/20
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
12 days ago*
Outbound flight: 12/30/19
19:50 BOS
21:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $153
12 days ago*
Outbound flight: 08/22/19
12:43 BOS
14:34 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines Return flight: 08/31/19
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines $156
78 days ago*