$93
Cheap
$93
$93
Expensive
$285
$285
Favorite airline: e.g. American Airlines, JetBlue Airways
Flight tickets on the route Boston – Chicago are most frequently booked with American Airlines.
American Airlines
13 %
JetBlue Airways
13 %
Southwest
11 %
Tip: book 15 days before departure
The best time to buy tickets is 15 days before the flight. Pay only $99.00.
Cheapest weekday: Saturday
Cheap flights on this route are operated on Saturday.
Direct flights are cheaper
On this route, direct flights are $10.00 cheaper than flights with a stopover.
non stop flight
1 stop
2 stops
02h 46min
11h 08min
05h 45min
$93
$103
$220
The favorite connection is non-stop
Flights from Boston to Chicago are most often booked as a direct flight.
Route
bookings
Direct flights
02h 46min, from $93
59 %
1 stopover Seattle-Tacoma International Airport, WA
17h 50min, from $255
9 %
1 stopover Baltimore-Washington International-Thurgood Marshall Airport, MD
11h 08min, from $103
9 %
Round trip from $93.00
The price of a ticket for a flight on 11/02/2019 returning on 11/09/2019 is currently $93.00.
Flights from Boston to Chicago
Outbound flight: 12/31/19
09:20 BOS
11:26 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/04/20
19:40 CHI
22:55 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines $135
44 days ago*
Outbound flight: 01/24/20
09:00 BOS
10:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/26/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $145
73 days ago*
Outbound flight: 01/24/20
12:00 BOS
13:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/26/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $145
73 days ago*
Outbound flight: 12/31/19
09:20 BOS
11:26 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/04/20
12:20 CHI
19:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Southwest Airlines $148
44 days ago*
Outbound flight: 01/24/20
19:59 BOS
21:49 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/26/20
07:45 CHI
11:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $150
73 days ago*
Outbound flight: 01/24/20
08:31 BOS
10:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/26/20
07:45 CHI
11:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $150
73 days ago*
Outbound flight: 01/24/20
12:00 BOS
13:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/26/20
09:00 CHI
15:42 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $152
73 days ago*
Outbound flight: 12/31/19
09:20 BOS
11:26 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/04/20
21:11 CHI
00:24 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $157
44 days ago*
Outbound flight: 01/24/20
19:59 BOS
22:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/26/20
15:35 CHI
19:14 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines $158
73 days ago*
Outbound flight: 12/31/19
12:07 BOS
14:12 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/04/20
19:40 CHI
22:55 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines $164
44 days ago*
Outbound flight: 12/31/19
17:45 BOS
19:55 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/04/20
19:40 CHI
22:55 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines $165
44 days ago*
Outbound flight: 01/24/20
14:57 BOS
17:00 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 01/26/20
12:30 CHI
18:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $168
73 days ago*
Outbound flight: 01/24/20
19:00 BOS
21:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 01/26/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $169
73 days ago*
Outbound flight: 01/24/20
19:00 BOS
21:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 01/26/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $169
73 days ago*
Outbound flight: 12/31/19
06:00 BOS
11:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/04/20
12:20 CHI
19:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Southwest Airlines $179
44 days ago*
Outbound flight: 12/31/19
06:00 BOS
11:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/04/20
12:20 CHI
19:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Southwest Airlines $179
44 days ago*
Outbound flight: 01/24/20
19:00 BOS
21:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 01/26/20
12:30 CHI
18:22 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $180
73 days ago*
Outbound flight: 01/24/20
19:59 BOS
21:49 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/26/20
09:00 CHI
15:42 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $182
73 days ago*
Outbound flight: 01/24/20
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/26/20
09:00 CHI
15:42 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $182
73 days ago*
Outbound flight: 12/31/19
20:20 BOS
22:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines Return flight: 01/04/20
12:20 CHI
19:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Southwest Airlines $184
44 days ago*