
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Kiwi.com) |
One-way from | $99 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $327 |
Good round-trip deal | $328 or less |
Good one-way deal | $168 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 5/6
7:25 pm-5:45 am
1 stop8h 20m
Chicago Midway
Sat 5/9
6:05 pm-8:25 pm
Nonstop4h 20m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sun 4/26
5:20 am-11:15 am
Nonstop3h 55m
Chicago Midway
Wed 4/29
8:50 pm-11:10 pm
Nonstop4h 20m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 4/20
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
Tue 4/21
8:50 pm-11:10 pm
Nonstop4h 20m
PortlandChicago
PDX - RFD
PDXRFD
Portland
Thu 4/30
7:46 pm-7:45 pm
1 stop21h 59m
Chicago Greater Rockford
Wed 5/6
2:51 pm-6:56 pm
1 stop30h 05m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 6/10
10:40 pm-4:45 am
Nonstop4h 05m
Chicago O'Hare Intl
Sun 6/14
7:05 am-9:39 am
Nonstop4h 34m
PortlandChicago
PDX - ORD
PDXORD
Portland
Mon 4/20
3:30 pm-1:28 am
1 stop7h 58m
Chicago O'Hare Intl
Tue 4/21
4:05 pm-6:34 pm
Nonstop4h 29m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 5/6
7:25 pm-5:45 am
1 stop8h 20m
Chicago Midway
Sun 5/10
9:45 pm-12:05 am
Nonstop4h 20m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/14
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
Thu 4/16
6:55 am-2:20 pm
1 stop9h 25m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 6/26
10:56 pm-5:00 am
Nonstop4h 04m
Chicago O'Hare Intl
Wed 7/1
2:12 pm-4:50 pm
Nonstop4h 38m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 6/30
11:05 am-8:05 pm
1 stop7h 00m
Chicago O'Hare Intl
Sun 7/5
8:57 am-11:38 am
Nonstop4h 41m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 43 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 $118). Flying from Portland to Chicago in July is currently the most expensive (average of $238). 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 18% on your trip compared to booking a flight in the morning.
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 Monday, which is when the least amount of flights are scheduled (15 on average).
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
robert,Feb 2026
LAS - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$99 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$286 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$180 | Average$311 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$370 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$340 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$231 | Average$372 | FlexibilityNo cancel fee | On-time63% |