
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $250 (Frontier) |
One-way from | $117 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $338 |
Good round-trip deal | $367 or less |
Good one-way deal | $204 or less |
Fly from
Fly to
Route
Depart
Return
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 5/9
7:10 am-10:20 pm
2 stops13h 10m
Chicago O'Hare Intl
Tue 5/12
4:50 pm-11:10 pm
1 stop8h 20m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 5/9
7:45 pm-5:40 am
1 stop7h 55m
Chicago O'Hare Intl
Wed 5/13
9:20 pm-11:55 pm
Nonstop4h 35m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 4/28
8:45 am-4:56 pm
1 stop6h 11m
Chicago O'Hare Intl
Wed 4/29
8:00 am-12:52 pm
1 stop6h 52m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 5/13
11:12 pm-8:45 am
1 stop7h 33m
Chicago O'Hare Intl
Wed 5/27
12:47 pm-5:11 pm
1 stop6h 24m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/22
5:00 pm-11:13 pm
Nonstop4h 13m
Chicago O'Hare Intl
Tue 7/28
4:15 pm-6:47 pm
Nonstop4h 32m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 4/28
2:35 pm-11:55 pm
1 stop7h 20m
Chicago O'Hare Intl
Thu 5/7
8:00 am-2:20 pm
1 stop8h 20m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/22
10:53 am-11:18 pm
1 stop10h 25m
Chicago O'Hare Intl
Tue 7/28
6:55 am-11:43 am
1 stop6h 48m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 8/26
1:59 pm-11:59 pm
1 stop8h 00m
Chicago O'Hare Intl
Fri 8/28
2:22 pm-4:50 pm
Nonstop4h 28m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/8
10:59 pm-5:00 am
Nonstop4h 01m
Chicago O'Hare Intl
Wed 7/15
6:20 am-1:43 pm
1 stop9h 23m
PortlandChicago
PDX - ORD
PDXORD
Portland
Thu 5/21
10:40 pm-4:45 am
Nonstop4h 05m
Chicago O'Hare Intl
Mon 5/25
5:00 am-9:47 am
1 stop6h 47m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, September is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $125). Flying from Portland to Chicago O'Hare Intl Airport 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.
When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 35% versus a flight in the morning.
Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport 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.
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
Entertainment
Overall
Crew
Boarding
Food
Comfort
Reviews
Eugene,Mar 2026
MFR - SEA
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$271 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$169 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$364 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$208 | Average$334 | FlexibilityNo cancel fee | On-time75% |