Favorite airline: JetBlue Airways
The favorite airline for flights from Chicago to Boston is JetBlue Airways.
JetBlue Airways
31 %
United Airlines
13 %
Spirit Airlines
10 %
Direct flights are the cheapest connection
Compared to flights with a stopover, direct flights are $65.00 cheaper on this route.
non stop flight
1 stop
02h 35min
04h 52min
$98
$163
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 61 % of travelers will book a direct flight.
Route
bookings
Direct flights
02h 35min, from $98
61 %
1 stopover New York - John F. Kennedy International Airport, NY
11h 33min, from $296
25 %
1 stopover New York - La Guardia Airport, NY
04h 52min, from $163
10 %

Flights from Chicago to Boston

IDEALO: 67 Flight Offers from $98
Outbound flight: 09/19/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$98
11 days ago*
Check
Outbound flight: 09/19/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$98
11 days ago*
Check
Outbound flight: 09/20/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$127
11 days ago*
Check
Outbound flight: 09/20/19
21:19 CHI
00:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$151
11 days ago*
Check
Outbound flight: 09/19/19
06:00 CHI
09:18 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 10/08/19
05:50 BOS
07:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$151
11 days ago*
Check
Outbound flight: 09/19/19
06:00 CHI
09:18 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 10/08/19
06:15 BOS
12:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$155
11 days ago*
Check
Outbound flight: 09/19/19
06:00 CHI
09:18 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 10/08/19
06:15 BOS
12:48 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$155
11 days ago*
Check
Outbound flight: 09/19/19
06:30 CHI
12:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 10/08/19
06:00 BOS
10:47 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$163
11 days ago*
Check
Outbound flight: 09/19/19
05:40 CHI
08:58 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$166
11 days ago*
Check
Outbound flight: 09/19/19
09:15 CHI
12:36 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$166
11 days ago*
Check
Outbound flight: 09/20/19
05:40 CHI
08:58 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$166
11 days ago*
Check
Outbound flight: 09/20/19
05:40 CHI
08:58 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$166
11 days ago*
Check
Outbound flight: 09/19/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
08:08 BOS
11:58 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$171
11 days ago*
Check
Outbound flight: 09/19/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
08:08 BOS
11:58 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$171
11 days ago*
Check
Outbound flight: 09/20/19
09:15 CHI
12:36 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 10/08/19
13:25 BOS
15:22 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Spirit Airlines
$178
11 days ago*
Check
Outbound flight: 09/20/19
07:30 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 10/08/19
05:50 BOS
07:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$185
11 days ago*
Check
Outbound flight: 09/20/19
07:30 CHI
14:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 10/08/19
05:50 BOS
07:45 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$185
11 days ago*
Check
Outbound flight: 09/20/19
10:40 CHI
14:01 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 10/08/19
10:24 BOS
12:19 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$196
11 days ago*
Check
Outbound flight: 09/20/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
08:30 BOS
20:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$198
11 days ago*
Check
Outbound flight: 09/20/19
13:46 CHI
17:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Spirit Airlines
Return flight: 10/08/19
08:30 BOS
20:07 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$198
11 days ago*
Check
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