Favorite airline: United Airlines
The most popular airline for flights from Boston to Chicago is United Airlines.
United Airlines
19 %
American Airlines
17 %
JetBlue Airways
14 %
Tip: book 5 days before departure
Save up to 63 % by booking flights 5 days before departure.
5 days before departure
Cheapest weekday: Thursday
Compared to other weekdays, flights are cheapest on Thursday.
Direct flights are cheaper
Direct flights on this route are $ 7.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
02h 41min
05h 13min
$146
$153
The favorite connection is non-stop
65 % of all bookings on the route Boston to Chicago are for non-stop flights.
Route
bookings
Direct flights
02h 41min, from $146
65 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
04h 28min, from $169
11 %
1 stopover New York - La Guardia Airport, NY
06h 53min, from $159
7 %
Round trip from $146.00
Flights on this route with a departure on 08/22/2019 and return flight on 08/31/2019 currently cost $146.00.

$146
Cheap
$86
Expensive
$293