Cheap Flights from Boston to Chicago

Prices were available within the past 7 days and starts at $19 for one-way flights and $37 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Reviews from verified customers

Mar 6, 2020

Left and arrived on time

Mar 3, 2020

Having to wait to get to the gate and then a while sitting there for seat assignment was stressful. Wasn’t sure if I would be fine or be on standby but it all worked out

Mar 2, 2020

Great experience...will definitely fly American from now on!

Mar 1, 2020

They were ontime an overall good experience!

Feb 29, 2020

Seats are WAY too narrow! I am fit, as we’re the people in my row, and we could barely move. Also, the rows are too close together.

Feb 28, 2020

The staff was very accommodating and friendly

Feb 19, 2020

What a great airline!!

Feb 14, 2020

Turbulence so no actual service but it was ok

Feb 13, 2020

Staff wasn’t that friendly until the final goodbye.

Jan 31, 2020

Wonderful staff on the flight

Boston to Chicago route information

Origin Airport Logan Intl.
Destination Airport O'Hare Intl.
Flight Price $36
Distance 863 mi