Portland (PDX) to Chicago (ORD) flight deal from $197 USD in economy class

UAUnited Airlines

Round Trip•Economy

PDX

Portland International Airport

Portland, United States

ORD

O'Hare International Airport

Chicago, United States

$304 USD

-35%$197 USD

Verified Nov 5, 2025 at 2:27 AM

December 2025

Today

Mon

Tue

Wed

Thu

Fri

Sat

Sun

1$316 2$197 3$197 4$201 5$201 6$201 7$205 8$205 9$201 10$201 11$205 12$215 13$260 14$264 15$264 16$260 17$274 18$250 19$392 20$268 21$318 22$253 23$306 24$225 25$205 26$237 27$222 28$276 29$233 30$247 31$207 1 2 3 4

Limited Availability

17% of dates checked are available within 10% of the lowest price

Thursday, December 18th, 2025

10 round-trip options

Returning

Tue, Dec 23, 2025•5 Day Trip

$301 USD

Google Flights

Returning

Wed, Dec 24, 2025•6 Day Trip

$264 USD

Google Flights

Returning

Thu, Dec 25, 2025•7 Day Trip

$324 USD

Google Flights

Returning

Fri, Dec 26, 2025•8 Day Trip

$283 USD

Google Flights

Returning

Sat, Dec 27, 2025•9 Day Trip

$574 USD

Google Flights

Returning

Sun, Dec 28, 2025•10 Day Trip

$608 USD

Google Flights

Returning

Mon, Dec 29, 2025•11 Day Trip

$290 USD

Google Flights

Returning

Tue, Dec 30, 2025•12 Day Trip

$405 USD

Google Flights

Returning

Wed, Dec 31, 2025•13 Day Trip

$331 USD

Google Flights

Returning

Thu, Jan 1, 2026•14 Day Trip

$250 USD

Google Flights