Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.
Economy Plus offers extra legroom and is free for MileagePlus Premier members.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $225 (Delta) |
One-way from | $109 (United Airlines) |
Popular in | March |
Cheapest in | August |
Average price | $293 |
Good round-trip deal | $318 or less |
Good one-way deal | $148 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 2/15
7:00 am-1:11 pm
Nonstop4h 11m
Chicago O'Hare Intl
Tue 2/17
2:07 pm-4:50 pm
Nonstop4h 43m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 2/18
1:36 pm-11:56 pm
1 stop8h 20m
Chicago O'Hare Intl
Sat 2/21
2:07 pm-4:50 pm
Nonstop4h 43m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 2/17
1:36 pm-11:56 pm
1 stop8h 20m
Chicago O'Hare Intl
Wed 3/11
2:07 pm-4:50 pm
Nonstop4h 43m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 2/14
1:36 pm-11:56 pm
1 stop8h 20m
Chicago O'Hare Intl
Wed 2/18
2:07 pm-4:50 pm
Nonstop4h 43m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 2/18
2:15 pm-9:50 pm
1 stop5h 35m
Chicago Midway
Wed 2/25
8:10 am-3:45 pm
1 stop9h 35m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 1/31
8:45 am-6:30 pm
2 stops7h 45m
Chicago Midway
Sat 2/7
8:35 am-11:15 am
Nonstop4h 40m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 1/31
6:00 am-11:55 am
Nonstop3h 55m
Chicago Midway
Thu 2/5
8:10 am-10:45 am
Nonstop4h 35m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 1/31
1:24 pm-9:15 pm
1 stop5h 51m
Chicago O'Hare Intl
Tue 2/3
5:16 pm-12:31 am
1 stop9h 15m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 1/11
5:30 am-1:22 pm
1 stop5h 52m
Chicago O'Hare Intl
Wed 1/14
2:20 pm-6:50 pm
1 stop6h 30m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 3/2
4:15 pm-5:05 am
1 stop10h 50m
Chicago Midway
Sat 3/7
10:30 pm-12:55 am
Nonstop4h 25m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star |
Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, August is the cheapest month in which you can book a flight from Portland to Chicago (average of $120). Flying from Portland to Chicago in March is currently the most expensive (average of $244). 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.
A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the evening.
Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Wednesday 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.
The most flights from PDX to CHI are scheduled on a Thursday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
Overall
Crew
Comfort
Food
Entertainment
Boarding
Reviews
Anonymous,Dec 2025
SEA - MSY
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$123 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$286 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$196 | Average$323 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$219 | Average$351 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$223 | Average$378 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$238 | Average$379 | FlexibilityNo cancel fee | On-time63% |