$132 Cheap Sun Country Airlines flights Chicago (ORD) to Portland (PDX)

Finding cheap one-way Sun Country Airlines flights from ORD to PDX from $132 on Expedia is easy — just filter by "Price (lowest to highest)." Or check out our budget-friendly round-trip fares from $278 for your next break.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Start searching one to three months ahead of your travel date to find cheap fares on Sun Country Airlines flights from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Get your timing right, and you can enjoy significant savings on domestic flights.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Browse Sun Country Airlines's earliest flights from ORD to PDX by checking the "Morning" and "Early Morning" filters. Not only will you arrive at your destination sooner, early departures are also 20% less likely to be canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.

Offering top-tier customer service and a rewarding loyalty program, Sun Country Airlines is a favorite for many travelers flying from ORD to PDX. What's more, if you're a Sun Country Rewards and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can be put toward future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.