Favorite airline: JetBlue Airways
Flight tickets on the route Chicago – Boston are most frequently booked with JetBlue Airways.
JetBlue Airways
16 %
United Airlines
12 %
Southwest
10 %
Direct flights are the cheapest connection
Compared to flights with a stopover, direct flights are $14.00 cheaper on this route.
non stop flight
1 stop
02h 23min
04h 44min
$159
$173
The favorite connection is non-stop
56 % of travelers decide to book a direct flight on this route.
Route
bookings
Direct flights
02h 23min, from $159
56 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
09h 24min, from $335
11 %
1 stopover New York - John F. Kennedy International Airport, NY
05h 25min, from $248
8 %

Flights from Chicago to Boston

IDEALO: 233 Flight Offers from $159
Outbound flight: 01/10/20
18:30 CHI
21:53 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 01/12/20
06:00 BOS
08:08 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$159
28 days ago*
Check
Outbound flight: 01/10/20
18:30 CHI
21:53 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
Return flight: 01/12/20
06:00 BOS
08:08 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$159
28 days ago*
Check
Outbound flight: 01/10/20
19:55 CHI
23:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$161
28 days ago*
Check
Outbound flight: 01/10/20
19:55 CHI
23:23 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$161
28 days ago*
Check
Outbound flight: 01/10/20
11:55 CHI
15:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$161
28 days ago*
Check
Outbound flight: 01/10/20
11:55 CHI
15:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$161
28 days ago*
Check
Outbound flight: 01/10/20
08:57 CHI
12:09 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$166
28 days ago*
Check
Outbound flight: 01/10/20
08:57 CHI
12:09 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$166
28 days ago*
Check
Outbound flight: 01/10/20
21:11 CHI
00:25 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$166
28 days ago*
Check
Outbound flight: 01/10/20
14:45 CHI
18:12 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$168
28 days ago*
Check
Outbound flight: 01/10/20
14:45 CHI
18:12 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$168
28 days ago*
Check
Outbound flight: 01/10/20
09:15 CHI
14:59 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$173
28 days ago*
Check
Outbound flight: 01/10/20
09:15 CHI
14:59 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/12/20
09:00 BOS
11:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$173
28 days ago*
Check
Outbound flight: 01/10/20
13:30 CHI
19:24 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$180
28 days ago*
Check
Outbound flight: 01/10/20
09:15 CHI
14:59 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$180
28 days ago*
Check
Outbound flight: 01/02/20
20:20 CHI
23:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 01/05/20
22:25 BOS
00:15 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$183
12 days ago*
Check
Outbound flight: 01/02/20
20:20 CHI
23:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 01/04/20
06:25 BOS
08:20 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$183
12 days ago*
Check
Outbound flight: 01/02/20
20:20 CHI
23:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 01/04/20
06:25 BOS
08:20 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$183
12 days ago*
Check
Outbound flight: 01/10/20
21:11 CHI
00:25 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$187
28 days ago*
Check
Outbound flight: 01/10/20
08:57 CHI
12:09 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
Return flight: 01/12/20
14:41 BOS
19:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$187
28 days ago*
Check
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