Boston (BOS) to Chicago (ORD) cheap flight deal from $117 USD in economy class

AAAmerican Airlines

Round Trip•Economy

BOS

Logan International Airport

Boston, United States

ORD

O'Hare International Airport

Chicago, United States

$249 USD

-53%$117 USD

Verified Sep 20, 2025 at 4:37 PM

October 2025

Today

Mon

Tue

Wed

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Sun

29$212 30$127 1$127 2$127 3$167 4$117 5$187 6$187 7$117 8$117 9$187 10$418 11$361 12$258 13$232 14$182 15$117 16$145 17$200 18$182 19$257 20$187 21$117 22$117 23$117 24$145 25$117 26$200 27$162 28$117 29$117 30$117 31$145 1 2

Extremely Rare Availability

4% of dates checked are available within 10% of the lowest price

Saturday, October 4th, 2025

10 round-trip options

Returning

Thu, Oct 9, 2025•5 Day Trip

$200 USD

Google Flights

Returning

Fri, Oct 10, 2025•6 Day Trip

$257 USD

Google Flights

Returning

Sat, Oct 11, 2025•7 Day Trip

$162 USD

Google Flights

Returning

Sun, Oct 12, 2025•8 Day Trip

$117 USD

Google Flights

Returning

Mon, Oct 13, 2025•9 Day Trip

$342 USD

Google Flights

Returning

Tue, Oct 14, 2025•10 Day Trip

$184 USD

Google Flights

Returning

Wed, Oct 15, 2025•11 Day Trip

$117 USD

Google Flights

Returning

Thu, Oct 16, 2025•12 Day Trip

$187 USD

Google Flights

Returning

Fri, Oct 17, 2025•13 Day Trip

$162 USD

Google Flights

Returning

Sat, Oct 18, 2025•14 Day Trip

$117 USD

Google Flights