$145
Cheap
$86
$86
Expensive
$294
$294
Favorite airline: United Airlines
United Airlines is the most popular airline for flights from Boston to Chicago.
United Airlines
25 %
American Airlines
24 %
Delta
16 %
Tip: book 5 weeks before departure
Our tip: book flights on this route 5 weeks before departure and save up to 57 %.
Cheapest weekday: Thursday
The cheapest days to fly on this route are Thursday.
Direct flights are the cheapest connection
Compared to direct flights, flights with a stopover on this route are on average 5 % more expensive.
non stop flight
1 stop
02h 41min
05h 13min
$145
$153
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 82 % of travelers will book a direct flight.
Route
bookings
Direct flights
02h 41min, from $145
82 %
1 stopover Philadelphia International Airport, PA
05h 13min, from $153
7 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
05h 08min, from $335
6 %
Round trip from $145.00
The best price roundtrip flight is currently available departing on 01/24/2020 and returning on 01/26/2020.
Flights from Boston to Chicago
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
18 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
18 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
18 days ago*
Outbound flight: 12/30/19
08:00 BOS
09:41 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/01/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
77 days ago*
Outbound flight: 12/30/19
07:02 BOS
09:02 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
21:05 CHI
00:19 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $149
77 days ago*
Outbound flight: 12/30/19
20:25 BOS
22:06 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 01/02/20
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $149
77 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
18 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
18 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
18 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
18 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
09:00 CHI
15:42 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $152
18 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
09:00 CHI
15:42 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $152
18 days ago*
Outbound flight: 12/30/19
19:50 BOS
21:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 01/02/20
06:00 CHI
09:10 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $153
77 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/02/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
77 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/02/20
09:50 CHI
13:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
77 days ago*
Outbound flight: 12/30/19
19:00 BOS
23:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines Return flight: 01/01/20
22:19 CHI
01:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $153
77 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
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $156
18 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
07:15 CHI
10:32 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $156
18 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
18 days ago*
Outbound flight: 01/24/20
08:55 BOS
10:59 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Delta Air Lines Return flight: 01/26/20
11:30 CHI
15:07 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Delta Air Lines $158
18 days ago*