Favorite airline: JetBlue Airways
The most popular airline for flights from Chicago to Boston is JetBlue Airways.
JetBlue Airways
31 %
United Airlines
16 %
Delta
15 %
Direct flights are cheaper
Direct flights on this route are $10.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 17min
05h 41min
$142
$152
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 64 % of travelers will book a direct flight.
Route
bookings
Direct flights
02h 17min, from $142
64 %
1 stopover New York - John F. Kennedy International Airport, NY
05h 37min, from $279
14 %
1 stopover Baltimore-Washington International-Thurgood Marshall Airport, MD
09h 48min, from $186
12 %

Flights from Chicago to Boston

IDEALO: 61 Flight Offers from $142
Outbound flight: 12/17/19
11:03 CHI
14:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 01/04/20
06:56 BOS
08:58 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$142
47 days ago*
Check
Outbound flight: 12/17/19
09:37 CHI
12:52 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 01/04/20
06:56 BOS
08:58 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$142
47 days ago*
Check
Outbound flight: 12/17/19
05:25 CHI
12:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/04/20
06:00 BOS
08:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$152
47 days ago*
Check
Outbound flight: 12/06/19
06:30 CHI
12:24 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 12/08/19
05:00 BOS
09:03 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$155
42 days ago*
Check
Outbound flight: 12/17/19
08:30 CHI
14:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/04/20
06:25 BOS
10:47 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$159
47 days ago*
Check
Outbound flight: 12/06/19
05:05 CHI
08:21 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 12/08/19
13:30 BOS
15:27 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$169
42 days ago*
Check
Outbound flight: 12/06/19
21:38 CHI
00:58 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 12/08/19
09:00 BOS
10:59 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$169
42 days ago*
Check
Outbound flight: 12/06/19
21:38 CHI
00:58 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 12/08/19
09:00 BOS
10:59 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$169
42 days ago*
Check
Outbound flight: 12/06/19
06:00 CHI
09:15 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 12/08/19
10:26 BOS
12:23 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$181
42 days ago*
Check
Outbound flight: 12/17/19
08:44 CHI
12:13 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/04/20
08:00 BOS
09:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$181
47 days ago*
Check
Outbound flight: 12/06/19
06:00 CHI
09:15 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 12/08/19
09:00 BOS
14:15 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$183
42 days ago*
Check
Outbound flight: 12/17/19
21:19 CHI
00:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/04/20
08:00 BOS
09:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$183
47 days ago*
Check
Outbound flight: 12/06/19
20:45 CHI
07:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Spirit Airlines
Return flight: 12/08/19
08:59 BOS
11:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
$186
42 days ago*
Check
Outbound flight: 12/06/19
20:45 CHI
07:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Spirit Airlines
Return flight: 12/08/19
08:59 BOS
11:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
$186
42 days ago*
Check
Outbound flight: 12/06/19
08:44 CHI
12:13 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 12/08/19
09:00 BOS
10:59 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$187
42 days ago*
Check
Outbound flight: 12/06/19
19:50 CHI
23:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 12/08/19
19:55 BOS
22:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
$187
42 days ago*
Check
Outbound flight: 12/06/19
08:44 CHI
12:13 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 12/08/19
09:00 BOS
10:59 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$187
42 days ago*
Check
Outbound flight: 12/06/19
19:50 CHI
23:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 12/08/19
19:55 BOS
22:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines
$187
42 days ago*
Check
Outbound flight: 12/06/19
20:45 CHI
07:33 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Spirit Airlines
Return flight: 12/08/19
09:00 BOS
13:18 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$189
42 days ago*
Check
Outbound flight: 12/17/19
11:03 CHI
14:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
Return flight: 01/04/20
22:40 BOS
00:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
$195
47 days ago*
Check
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