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 12 hours ago
Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Wednesday, December 23rd, 2026

8 round-trip options

Returning
Mon, Dec 28, 2026•5 Day Trip
$416 USD
Google Flights
Returning
Tue, Dec 29, 2026•6 Day Trip
$375 USD
Google Flights
Returning
Wed, Dec 30, 2026•7 Day Trip
$325 USD
Google Flights
Returning
Fri, Jan 1, 2027•9 Day Trip
$295 USD
Google Flights
Returning
Sat, Jan 2, 2027•10 Day Trip
$355 USD
Google Flights
Returning
Sun, Jan 3, 2027•11 Day Trip
$356 USD
Google Flights
Returning
Tue, Jan 5, 2027•13 Day Trip
$295 USD
Google Flights
Returning
Wed, Jan 6, 2027•14 Day Trip
$295 USD
Google Flights