Boston (BOS) to Chicago (ORD) flight deal from $139 USD in economy class

UAUnited Airlines

Round Trip•Economy

BOS

Logan International Airport

Boston, United States

ORD

O'Hare International Airport

Chicago, United States

$250 USD

-44%$139 USD

Verified Apr 8, 2026 at 7:13 PM

April 2026

Today

Mon

Tue

Wed

Thu

Fri

Sat

Sun

30 31 1 2 3 4 5 6 7 8$305 9$305 10$305 11$200 12$200 13$200 14$170 15$170 16$306 17$590 18$609 19$337 20$212 21$309 22$155 23$168 24$168 25$163 26$168 27$168 28$147 29$139 30$158 1$158 2$153 3$158

Extremely Rare Availability

1% of dates checked are available within 10% of the lowest price

Tuesday, April 14th, 2026

10 round-trip options

Returning

Sun, Apr 19, 2026•5 Day Trip

$215 USD

Google Flights

Returning

Mon, Apr 20, 2026•6 Day Trip

$215 USD

Google Flights

Returning

Tue, Apr 21, 2026•7 Day Trip

$185 USD

Google Flights

Returning

Wed, Apr 22, 2026•8 Day Trip

$170 USD

Google Flights

Returning

Thu, Apr 23, 2026•9 Day Trip

$191 USD

Google Flights

Returning

Fri, Apr 24, 2026•10 Day Trip

$315 USD

Google Flights

Returning

Sat, Apr 25, 2026•11 Day Trip

$568 USD

Google Flights

Returning

Sun, Apr 26, 2026•12 Day Trip

$357 USD

Google Flights

Returning

Mon, Apr 27, 2026•13 Day Trip

$285 USD

Google Flights

Returning

Tue, Apr 28, 2026•14 Day Trip

$178 USD

Google Flights