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
$129 - $266
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 4/16
2 stops22h 31m
Chicago O'Hare Intl
Tue 4/23
1 stop7h 32m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Mon 4/15
1 stop21h 57m
Chicago O'Hare Intl
Wed 4/24
1 stop7h 32m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 4/9
1 stop21h 57m
Chicago O'Hare Intl
Tue 4/16
1 stop15h 40m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 4/23
1 stop11h 19m
Chicago O'Hare Intl
Wed 5/1
1 stop7h 32m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 4/17
1 stop12h 32m
Chicago O'Hare Intl
Tue 4/23
1 stop15h 40m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 4/23
Nonstop4h 10m
Chicago O'Hare Intl
Wed 5/1
Nonstop4h 34m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Fri 4/19
1 stop7h 47m
Chicago Midway
Sat 4/27
1 stop8h 06m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/1
Nonstop4h 06m
Chicago O'Hare Intl
Sun 5/5
1 stop6h 32m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Sat 4/20
Nonstop3h 58m
Chicago O'Hare Intl
Sat 4/27
1 stop9h 22m
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Overall
Boarding
Crew
Comfort
Entertainment
Food
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
88%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
11%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Oregon to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
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.