
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Trip.com) |
One-way from | $134 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $435 |
Good round-trip deal | $309 or less |
Good one-way deal | $153 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 4/22
4:00 pm-11:10 pm
2 stops9h 10m
Portland
Tue 4/28
5:00 pm-5:50 am
2 stops10h 50m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 4/16
9:50 pm-12:10 am
Nonstop4h 20m
Portland
Sat 4/18
11:55 pm-5:50 am
Nonstop3h 55m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 5/6
8:50 pm-11:10 pm
Nonstop4h 20m
Portland
Sun 5/10
5:20 am-11:15 am
Nonstop3h 55m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 5/19
11:55 am-9:00 pm
2 stops11h 05m
Portland
Tue 6/2
6:40 am-3:00 pm
1 stop6h 20m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Mon 5/11
6:00 am-12:52 pm
1 stop8h 52m
Portland
Tue 5/12
10:56 pm-5:05 am
Nonstop4h 09m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 4/23
9:50 pm-12:10 am
Nonstop4h 20m
Portland
Sat 4/25
11:55 pm-5:50 am
Nonstop3h 55m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Mon 6/22
7:05 am-9:39 am
Nonstop4h 34m
Portland
Sat 6/27
10:40 pm-4:45 am
Nonstop4h 05m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 8/5
2:42 pm-10:13 pm
1 stop9h 31m
Portland
Wed 8/12
6:30 am-5:30 pm
1 stop9h 00m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 5/13
11:55 am-10:00 pm
2 stops12h 05m
Portland
Fri 5/15
10:45 am-10:55 pm
2 stops10h 10m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Thu 9/24
7:00 am-9:28 am
Nonstop4h 28m
Portland
Mon 9/28
5:35 pm-11:41 pm
Nonstop4h 06m
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 79 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.
Currently, January is the cheapest month in which you can book a flight from Chicago to Portland (average of $133). Flying from Chicago to Portland in December is currently the most expensive (average of $207). 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.
Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Saturday mornings 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.
The most flights from CHI to PDX are scheduled on a Tuesday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Entertainment
Boarding
Food
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$124 | Average$259 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$232 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$310 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$194 | Average$343 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$200 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$383 | FlexibilityNo cancel fee | On-time63% |