Travelers have found it’s best to book a flight 16 days in advance to save up to 124% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 16 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Oregon to Chicago 1-2 weeks in advance for as low as $528, or $743 for flights within the next 24 hours.
Our data shows that January tends to be the cheapest month to fly to Chicago from Oregon. Users have commonly found prices around $377 for the month, but tickets can be as low as $149. Due to multiple factors, prepare for potentially higher prices in June.
When flying from Oregon to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$67 - $216
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/22
Nonstop3h 50m
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/22
Nonstop3h 50m
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/22
Nonstop3h 50m
Chicago O'Hare Intl
Wed 5/29
1 stop8h 17m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/22
Nonstop3h 50m
Chicago O'Hare Intl
Mon 6/3
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Thu 5/16
Nonstop3h 50m
Chicago O'Hare Intl
Tue 5/21
2 stops25h 21m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Fri 5/17
2 stops31h 06m
Chicago O'Hare Intl
Tue 5/21
2 stops25h 21m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Thu 8/15
Nonstop4h 04m
Chicago O'Hare Intl
Sat 8/31
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 6/5
Nonstop3h 58m
Chicago O'Hare Intl
Wed 6/12
Nonstop4h 28m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Sat 5/25
1 stop8h 22m
Chicago Midway
Thu 5/30
1 stop6h 13m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Crew
Overall
Comfort
Entertainment
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
6%of flight departures | Early morningMidnight to 6 am |
---|---|
69%of flight departures | Morning6 am to noon |
17%of flight departures | AfternoonNoon to 6 pm |
8%of flight departures | Evening6 pm to midnight |
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Cheapflights simply makes it quick and affordable to book flights from Oregon to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Oregon to Chicago, users can toggle the no change fees filter when performing a flight search.
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Oregon today and book when prices fit your budget.