$154
Cheap
$0
$0
Expensive
$0
$0
Favorite airline: American Airlines
Flight tickets on the route Boston – Chicago are most frequently booked with American Airlines.
American Airlines
15 %
United Airlines
13 %
JetBlue Airways
11 %
Tip: book 6 weeks before departure
Save up to 51 % by booking flights 6 weeks before departure.
Cheapest weekday: Thursday
Choosing the right day of the week is worthwhile as prices of flights on this route are cheapest on Thursday.
Direct flights are cheaper
Direct flights on this route are $24.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
03h 01min
06h 20min
$154
$178
The favorite connection is non-stop
61 % of all bookings on the route Boston to Chicago are for non-stop flights.
Route
bookings
Direct flights
03h 01min, from $154
61 %
1 stopover Washington DC - Dulles International Airport, DC
04h 12min, from $293
19 %
1 stopover Port Columbus International Airport, OH
04h 30min, from $286
11 %
Round trip from $154.00
A roundtrip costing only $154.00 is for example available departing 04/03/2019 and returning 04/07/2019.
Flights from Boston to Chicago
Outbound flight: 04/03/19
06:00 BOS
08:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $154
61 days ago*
Outbound flight: 04/03/19
06:00 BOS
08:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $172
61 days ago*
Outbound flight: 04/03/19
06:00 BOS
08:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $172
61 days ago*
Outbound flight: 04/03/19
12:38 BOS
17:58 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $179
61 days ago*
Outbound flight: 04/03/19
16:05 BOS
00:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $194
61 days ago*
Outbound flight: 04/03/19
19:57 BOS
21:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 04/07/19
06:02 CHI
09:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $218
61 days ago*
Outbound flight: 04/03/19
19:57 BOS
21:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 04/07/19
06:02 CHI
09:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $218
61 days ago*
Outbound flight: 04/03/19
06:00 BOS
08:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
JetBlue Airways Return flight: 04/07/19
11:36 CHI
17:25 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines $229
61 days ago*
Outbound flight: 04/03/19
06:25 BOS
08:13 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 04/07/19
11:36 CHI
17:25 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines $230
61 days ago*
Outbound flight: 04/03/19
14:00 BOS
18:00 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Delta Air Lines Return flight: 04/07/19
11:02 CHI
15:56 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
Delta Air Lines $230
61 days ago*
Outbound flight: 04/03/19
05:10 BOS
07:10 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 04/07/19
07:20 CHI
10:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $234
61 days ago*
Outbound flight: 04/03/19
19:57 BOS
21:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 04/07/19
06:02 CHI
09:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $244
61 days ago*
Outbound flight: 04/03/19
06:50 BOS
08:57 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 04/07/19
08:30 CHI
14:08 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $253
61 days ago*
Outbound flight: 04/03/19
20:36 BOS
00:01 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
JetBlue Airways Return flight: 04/07/19
05:45 CHI
09:06 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
JetBlue Airways $271
61 days ago*
Outbound flight: 04/03/19
19:25 BOS
21:24 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 04/07/19
05:00 CHI
10:05 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
1 Stopover
American Airlines $271
61 days ago*
Outbound flight: 04/03/19
19:25 BOS
21:24 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines Return flight: 04/07/19
07:20 CHI
10:38 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
American Airlines $281
61 days ago*
Outbound flight: 06/07/19
06:10 BOS
09:40 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Southwest Airlines Return flight: 06/21/19
22:30 CHI
01:40 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines $286
57 days ago*
Outbound flight: 06/07/19
19:35 BOS
21:20 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Southwest Airlines Return flight: 06/21/19
22:30 CHI
01:40 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
Southwest Airlines $288
57 days ago*
Outbound flight: 04/03/19
19:45 BOS
22:57 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
United Airlines Return flight: 04/07/19
06:02 CHI
09:20 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $293
61 days ago*
Outbound flight: 04/03/19
19:57 BOS
21:51 CHI
Boston Logan International Airport, MA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
United Airlines Return flight: 04/07/19
21:33 CHI
00:50 BOS
Chicago-IL all Airports (ORD, MDW, RFD)
Boston Logan International Airport, MA
direct
United Airlines $295
61 days ago*