Boston (BOS) to Chicago (ORD) flight deal in economy from $149

American AirlinesAAAmerican Airlines
Round Trip•Economy
United StatesBOS

Logan International Airport

Boston, United States
United StatesORD

O'Hare International Airport

Chicago, United States
$237 USD
-37%$149 USD
Verified about 6 hours ago
Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Wednesday, August 5th, 2026

3 round-trip options

Returning
Tue, Aug 11, 2026•6 Day Trip
$149 USD
Google Flights
Returning
Tue, Aug 18, 2026•13 Day Trip
$149 USD
Google Flights
Returning
Wed, Aug 19, 2026•14 Day Trip
$149 USD
Google Flights