Travelers have found it’s best to book a flight 59 days in advance to save up to 23% 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 59 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 $332, or $615 for flights within the next 24 hours.
Our data shows that November tends to be the cheapest month to fly to Chicago from Oregon. Users have commonly found prices around $361 for the month, but tickets can be as low as $127. 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
$84 - $227
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 6/12
Nonstop4h 07m
Chicago O'Hare Intl
Wed 6/19
Nonstop4h 27m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 8/21
Nonstop3h 50m
Chicago O'Hare Intl
Wed 8/28
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 8/28
Nonstop3h 50m
Chicago O'Hare Intl
Sun 9/1
Nonstop4h 30m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Fri 6/14
Nonstop4h 07m
Chicago O'Hare Intl
Wed 6/19
Nonstop4h 27m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 8/28
Nonstop3h 50m
Chicago O'Hare Intl
Sat 8/31
1 stop7h 44m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Wed 9/4
1 stop9h 04m
Chicago Midway
Tue 9/17
1 stop19h 40m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 8/20
Nonstop4h 02m
Chicago O'Hare Intl
Fri 8/23
Nonstop4h 31m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 7/9
Nonstop4h 04m
Chicago O'Hare Intl
Fri 7/12
1 stop7h 21m
Boise Air Term. Gowen FldChicago O'Hare Intl
BOI - ORD
BOIORD
Boise Air Term. Gowen Fld
Sat 7/20
1 stop8h 08m
Chicago O'Hare Intl
Tue 7/23
1 stop9h 11m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
4%of flight departures | Early morningMidnight to 6 am |
---|---|
47%of flight departures | Morning6 am to noon |
26%of flight departures | AfternoonNoon to 6 pm |
23%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.