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

American AirlinesAAAmerican Airlines
Round Trip•Economy
United StatesORD

O'Hare International Airport

Chicago, United States
United StatesBOS

Logan International Airport

Boston, United States
$232 USD
-36%$149 USD
Verified about 20 hours ago
Rare Availability
7% of dates checked are available within 10% of the lowest price

Tuesday, December 22nd, 2026

8 round-trip options

Returning
Sun, Dec 27, 2026•5 Day Trip
$374 USD
Google Flights
Returning
Mon, Dec 28, 2026•6 Day Trip
$336 USD
Google Flights
Returning
Wed, Dec 30, 2026•8 Day Trip
$215 USD
Google Flights
Returning
Thu, Dec 31, 2026•9 Day Trip
$215 USD
Google Flights
Returning
Fri, Jan 1, 2027•10 Day Trip
$215 USD
Google Flights
Returning
Sat, Jan 2, 2027•11 Day Trip
$255 USD
Google Flights
Returning
Sun, Jan 3, 2027•12 Day Trip
$313 USD
Google Flights
Returning
Tue, Jan 5, 2027•14 Day Trip
$215 USD
Google Flights