
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (Kiwi.com) |
One-way from | $153 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $357 |
Good round-trip deal | $315 or less |
Good one-way deal | $163 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 7/4
7:20 am-9:45 am
Nonstop4h 25m
Portland
Tue 7/7
10:59 pm-5:00 am
Nonstop4h 01m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 7/22
9:10 pm-11:35 pm
Nonstop4h 25m
Portland
Tue 7/28
7:50 pm-5:45 am
1 stop7h 55m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 8/21
8:50 pm-11:05 pm
Nonstop4h 15m
Portland
Sat 8/22
11:30 pm-5:25 am
Nonstop3h 55m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 8/18
6:00 am-11:21 am
1 stop7h 21m
Portland
Tue 8/25
7:06 am-1:26 pm
Nonstop4h 20m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 7/29
5:05 am-10:00 am
1 stop6h 55m
Portland
Tue 8/4
6:25 pm-5:45 am
1 stop9h 20m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 7/14
9:10 pm-11:35 pm
Nonstop4h 25m
Portland
Fri 7/17
11:30 pm-5:20 am
Nonstop3h 50m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 7/3
7:20 am-9:45 am
Nonstop4h 25m
Portland
Mon 7/6
10:59 pm-5:00 am
Nonstop4h 01m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 7/5
7:20 am-9:45 am
Nonstop4h 25m
Portland
Sun 7/12
10:59 pm-5:00 am
Nonstop4h 01m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 8/5
7:00 am-2:45 pm
1 stop9h 45m
Portland
Wed 8/12
1:30 pm-9:47 pm
1 stop6h 17m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 8/19
8:35 am-3:25 pm
2 stops8h 50m
Portland
Tue 8/25
7:50 am-7:50 pm
2 stops10h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
Currently, August is the cheapest month in which you can book a flight from Chicago to Portland (average of $94). Flying from Chicago to Portland in July is currently the most expensive (average of $697). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike at noon, when flights are generally more expensive, you can save up to 19% on flights from Chicago to Portland by exploring options for tickets in the evening.
The most flights from CHI to PDX are scheduled on a Thursday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 on average).
To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Food
Overall
Boarding
Entertainment
Crew
Reviews
Walter,May 2026
LAS - BUR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$247 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$319 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$329 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$201 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$357 | FlexibilityNo cancel fee | On-time63% |