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.
15 days before departure
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.

$93
Cheap
$93
Expensive
$285