Favorite airline: Delta
56 % of flights from Chicago to Boston are booked with Delta.
Delta
56 %
Southwest
44 %
Direct flights are the cheapest connection
Compared to flights with a stopover, direct flights are $18.00 cheaper on this route.
non stop flight
1 stop
02h 15min
03h 29min
$174
$192
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 80 % of travelers will book a direct flight.
Route
bookings
Direct flights
02h 15min, from $174
80 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
05h 58min, from $289
20 %

Flights from Chicago to Boston

IDEALO: 41 Flight Offers from $135
Outbound flight: 03/22/19
09:00 CHI
12:18 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$135
77 days ago*
Check
Outbound flight: 03/22/19
21:33 CHI
00:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$135
77 days ago*
Check
Outbound flight: 03/23/19
20:21 CHI
23:39 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
$139
77 days ago*
Check
Outbound flight: 03/23/19
20:21 CHI
23:39 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
$146
75 days ago*
Check
Outbound flight: 03/22/19
22:20 CHI
01:35 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
$147
77 days ago*
Check
Outbound flight: 05/08/19
06:05 CHI
09:15 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 05/22/19
08:35 BOS
10:20 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$174
79 days ago*
Check
Outbound flight: 05/08/19
22:00 CHI
01:15 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 05/22/19
14:25 BOS
16:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$174
79 days ago*
Check
Outbound flight: 05/08/19
09:22 CHI
13:51 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
Return flight: 05/22/19
14:25 BOS
16:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$192
79 days ago*
Check
Outbound flight: 03/22/19
09:30 CHI
15:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$197
77 days ago*
Check
Outbound flight: 03/23/19
12:25 CHI
17:49 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines
$197
75 days ago*
Check
Outbound flight: 03/22/19
19:00 CHI
22:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$219
77 days ago*
Check
Outbound flight: 03/22/19
19:00 CHI
22:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$219
77 days ago*
Check
Outbound flight: 07/15/19
22:30 CHI
01:40 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 07/29/19
08:50 BOS
10:35 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
$250
8 days ago*
Check
Outbound flight: 03/23/19
16:01 CHI
23:46 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$251
75 days ago*
Check
Outbound flight: 03/23/19
16:01 CHI
23:46 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$252
77 days ago*
Check
Outbound flight: 03/22/19
06:47 CHI
14:02 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
United Airlines
$256
77 days ago*
Check
Outbound flight: 03/22/19
20:30 CHI
11:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
$257
77 days ago*
Check
Outbound flight: 07/15/19
22:30 CHI
01:40 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 07/29/19
15:25 BOS
20:00 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Southwest Airlines
$264
8 days ago*
Check
Outbound flight: 07/15/19
22:30 CHI
01:40 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
Return flight: 07/29/19
15:25 BOS
20:00 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Southwest Airlines
$264
8 days ago*
Check
Outbound flight: 03/23/19
15:11 CHI
22:35 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines
$266
75 days ago*
Check
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