$129 Cheap Sun Country Airlines flights Portland (PDX) to Chicago (ORD)

View $129 flight on Sun, Oct 5, 2025Opens in a new window

$129 Cheap Sun Country Airlines flights Portland (PDX) to Chicago (ORD)

Prices were available within the past 7 days and start at $129 for one-way flights and $257 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun Country Airlines
Sun, Oct 5 - Mon, Oct 6
PDX
Portland
ORD
Chicago
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago
Select Sun Country Airlines flight, departing Sun, Oct 5 from Portland to Chicago, returning Mon, Oct 6, priced at $257 found 2 hours ago
Flights from Portland (PDX) to Chicago (ORD)
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Popular airline
Alaska Airlines
Distance
1734 mi
Average flight time
6 hours 9 mins

Frequently asked questions

How much is a Sun Country Airlines flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Finding cheap one-way Sun Country Airlines flights from PDX to ORD from $129 on Expedia is easy — just filter by "Price (lowest to highest)." Or check out our budget-friendly round-trip fares from $257 for your next exciting vacation.**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.
What is the cheapest month to fly from PDX to ORD with Sun Country Airlines?
Sun Country Airlines flights to Chicago are typically more affordable in the off-peak months of January and February. Whether you're in search of a one-way or round-trip ticket, you could score a better deal then.
What is the cheapest time to book flights from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) with Sun Country Airlines?
For cheap Sun Country Airlines fares from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also impact the overall price. Sunday is typically the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight on a Sunday.**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.
Does Sun Country Airlines fly nonstop from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Use the "Nonstop" filter when searching for direct Sun Country Airlines flights from PDX to ORD. It's also a great way to compare other carriers offering the same direct trip.
What is the earliest Sun Country Airlines flight from PDX to ORD?
To find the earliest departure from PDX to ORD with Sun Country Airlines, filter your results by "Early Morning" and "Morning." Booking an early flight usually means you're less likely to experience cancellations.**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.
What airports does Sun Country Airlines fly into in Chicago?
O'Hare Intl. Airport (ORD) is the primary Chicago gateway for Sun Country Airlines flights from Portland Intl. Airport (PDX).
What kind of luggage can I take on a Sun Country Airlines flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
You're permitted 1 cabin bag weighing up to 33 lb and dimensions no larger than 23 inches x 10 inches x 15 inches. You may also bring a small personal item with you when flying standard economy from PDX to ORD with Sun Country Airlines. Baggage limits can differ by cabin class and airfare type, so check Sun Country Airlines's website to avoid last-minute fees at the airport.
Why fly with Sun Country Airlines from PDX to ORD?
Taking off from PDX to ORD with Sun Country Airlines comes with a range of perks, such as top-tier customer service and a rewarding loyalty program. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to redeem on select future travel purchases. That's in addition to the Sun Country Rewards points you can earn with Sun Country Airlines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Sun Country Airlines flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Typically, you can modify or cancel your flight, although there may be additional charges if you made your booking over 24 hours ago. Need to keep your options open? Make use of our "Changes included" or "No cancel fee" filter to find flights that won't charge extra if you need to revise your plans. To make changes, visit "Trips," select your flight and click on "Manage Booking" for more details.

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*Available to One Key members.