Boston (BOS) to Chicago (ORD) flight deal from $127 USD in economy class

UAUnited Airlines

Round Trip•Economy

BOS

Logan International Airport

Boston, United States

ORD

O'Hare International Airport

Chicago, United States

$196 USD

-35%$127 USD

Verified Nov 30, 2025 at 2:25 AM

December 2025

Today

Mon

Tue

Wed

Thu

Fri

Sat

Sun

1$260 2$235 3$235 4$235 5$235 6$127 7$127 8$127 9$127 10$127 11$127 12$151 13$137 14$137 15$137 16$148 17$165 18$207 19$302 20$302 21$226 22$255 23$247 24$263 25$190 26$237 27$303 28$267 29$196 30$180 31$127 1$127 2$137 3$169 4$157

Good Availability

44% of dates checked are available within 10% of the lowest price

Monday, December 1st, 2025

10 round-trip options

Returning

Sat, Dec 6, 2025•5 Day Trip

$543 USD

Google Flights

Returning

Sun, Dec 7, 2025•6 Day Trip

$260 USD

Google Flights

Returning

Mon, Dec 8, 2025•7 Day Trip

$538 USD

Google Flights

Returning

Tue, Dec 9, 2025•8 Day Trip

$622 USD

Google Flights

Returning

Wed, Dec 10, 2025•9 Day Trip

$597 USD

Google Flights

Returning

Thu, Dec 11, 2025•10 Day Trip

$503 USD

Google Flights

Returning

Fri, Dec 12, 2025•11 Day Trip

$503 USD

Google Flights

Returning

Sat, Dec 13, 2025•12 Day Trip

$538 USD

Google Flights

Returning

Sun, Dec 14, 2025•13 Day Trip

$511 USD

Google Flights

Returning

Mon, Dec 15, 2025•14 Day Trip

$737 USD

Google Flights