Favorite airline: United Airlines
Most travelers looking for flights on the route from Boston to Chicago decide to book flights with United Airlines.
United Airlines
24 %
American Airlines
16 %
Southwest
10 %
Tip: book 21 days before departure
Our tip: book flights on this route 21 days before departure and save up to 44 %.
21 days before departure
Cheapest weekday: Thursday
The cheapest days to fly on this route are Thursday.
Direct flights are cheaper
On this route, direct flights are $52.00 cheaper than flights with a stopover.
non stop flight
1 stop
03h 03min
04h 27min
$140
$192
The favorite connection is non-stop
81 % of travelers decide to book a direct flight on this route.
Route
bookings
Direct flights
03h 03min, from $140
81 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
04h 27min, from $192
11 %
1 stopover New York - John F. Kennedy International Airport, NY
05h 47min, from $216
6 %
Round trip from $140.00
A roundtrip costing only $140.00 is for example available departing 01/25/2019 and returning 01/27/2019.

$140
Cheap
$86
Expensive
$294

Flights from Boston to Chicago

IDEALO: 49 Flight Offers from $140
Outbound flight: 01/25/19
07:05 BOS
09:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
19:15 BOS
21:17 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
26 days ago*
Check
Outbound flight: 01/25/19
09:40 BOS
11:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$140
26 days ago*
Check
Outbound flight: 01/25/19
05:06 BOS
07:09 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
26 days ago*
Check
Outbound flight: 01/25/19
19:15 BOS
21:17 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
26 days ago*
Check
Outbound flight: 01/25/19
05:06 BOS
07:09 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
26 days ago*
Check
Outbound flight: 01/25/19
05:06 BOS
07:09 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
19:15 BOS
21:17 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
09:40 BOS
11:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
19:15 BOS
21:17 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
05:06 BOS
07:09 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 01/27/19
08:25 CHI
11:37 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines
$140
18 days ago*
Check
Outbound flight: 01/25/19
07:05 BOS
09:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
21:33 CHI
00:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$149
26 days ago*
Check
Outbound flight: 01/25/19
09:40 BOS
11:37 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
21:33 CHI
00:45 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$149
26 days ago*
Check
Outbound flight: 01/25/19
06:26 BOS
08:28 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways
Return flight: 01/27/19
05:40 CHI
08:59 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways
$172
18 days ago*
Check
Outbound flight: 01/25/19
08:25 BOS
10:21 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
21:20 CHI
00:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
$173
18 days ago*
Check
Outbound flight: 01/25/19
05:45 BOS
07:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$173
18 days ago*
Check
Outbound flight: 01/25/19
08:25 BOS
10:21 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines
Return flight: 01/27/19
21:20 CHI
00:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
$173
18 days ago*
Check
Outbound flight: 01/25/19
05:45 BOS
07:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$173
18 days ago*
Check
Outbound flight: 01/25/19
14:20 BOS
16:05 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
Return flight: 01/27/19
21:20 CHI
00:30 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines
$174
18 days ago*
Check
Outbound flight: 01/25/19
05:45 BOS
07:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines
Return flight: 01/27/19
06:35 CHI
09:48 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines
$174
26 days ago*
Check
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