Travelers have found it’s best to book a flight 47 days in advance to save up to 132% 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 47 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 Chicago to Oregon 1-2 weeks in advance for as low as $469, or $739 for flights within the next 24 hours.
January is one of the best times of the year to fly to Oregon from Chicago. Prices for January average $383 per person but you can even find prices for as low as $149. The most expensive prices can be found in the month of June. Opting for a January flight can save you 23% on your journey compared to booking in June
When flying from Chicago to Oregon, 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
$137 - $264
Route
Depart
Return
Price
Chicago MidwayPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 5/10
1 stop12h 21m
Portland
Mon 5/13
1 stop8h 39m
Chicago MidwayPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 5/8
1 stop27h 46m
Portland
Mon 5/13
1 stop8h 39m
Chicago MidwayPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 5/18
1 stop13h 10m
Portland
Sun 5/19
1 stop11h 05m
Chicago O'Hare IntlPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 5/17
Nonstop4h 30m
Portland
Sun 5/19
1 stop22h 00m
Chicago O'Hare IntlPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 6/11
1 stop14h 40m
Portland
Mon 6/17
Nonstop4h 07m
Chicago O'Hare IntlPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 6/4
Nonstop4h 28m
Portland
Fri 6/7
Nonstop3h 58m
Chicago O'Hare IntlEugene
ORD - EUG
ORDEUG
Chicago O'Hare Intl
Wed 9/11
1 stop8h 51m
Eugene
Tue 9/17
1 stop7h 59m
Chicago MidwayPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 5/25
1 stop8h 25m
Portland
Mon 5/27
1 stop6h 07m
Chicago O'Hare IntlEugene
ORD - EUG
ORDEUG
Chicago O'Hare Intl
Wed 5/15
1 stop18h 24m
Eugene
Wed 5/29
1 stop19h 17m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Boarding
Entertainment
Comfort
Crew
Food
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
41%of flight departures | Morning6 am to noon |
30%of flight departures | AfternoonNoon to 6 pm |
28%of flight departures | Evening6 pm to midnight |
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