Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.
Prepay checked bags 24 hours before to save on fees.
Round-trip from | $195 (Frontier) |
---|---|
One-way from | $110 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $315 |
Good round-trip deal | $324 or less |
Good one-way deal | $169 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 10/28
7:00 am-1:09 pm
Nonstop4h 09m
Chicago O'Hare Intl
Tue 11/4
2:05 pm-4:41 pm
Nonstop4h 36m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 10/22
11:00 pm-5:01 am
Nonstop4h 01m
Chicago O'Hare Intl
Wed 10/29
2:54 pm-8:46 pm
1 stop7h 52m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 10/28
7:00 am-1:09 pm
Nonstop4h 09m
Chicago O'Hare Intl
Tue 11/4
2:54 pm-8:46 pm
1 stop7h 52m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 10/10
11:00 pm-5:01 am
Nonstop4h 01m
Chicago O'Hare Intl
Tue 10/14
7:59 pm-9:44 am
1 stop15h 45m
PortlandChicago
PDX - ORD
PDXORD
Portland
Thu 2/5
10:47 am-4:48 pm
Nonstop4h 01m
Chicago O'Hare Intl
Sun 2/8
9:10 am-11:57 am
Nonstop4h 47m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 11/23
11:00 pm-5:01 am
Nonstop4h 01m
Chicago O'Hare Intl
Fri 11/28
7:00 am-9:39 am
Nonstop4h 39m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/10
8:45 pm-5:04 am
1 stop6h 19m
Chicago O'Hare Intl
Wed 3/11
7:45 am-1:46 pm
1 stop8h 01m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 12/9
12:32 am-8:40 am
1 stop6h 08m
Chicago O'Hare Intl
Mon 12/15
5:03 pm-10:09 pm
1 stop7h 06m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 10/17
11:00 pm-5:01 am
Nonstop4h 01m
Chicago O'Hare Intl
Mon 10/20
7:59 pm-9:44 am
1 stop15h 45m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 10/10
11:00 pm-5:01 am
Nonstop4h 01m
Chicago O'Hare Intl
Wed 10/15
8:20 am-4:50 pm
1 stop10h 30m
Booking 88 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, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $245). Flying from Portland to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 41% versus a flight in the morning.
Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport 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.
Las Vegas (LAS) – chosen by Cheapflights users on 83% of 1-stop itineraries from Portland to Chicago O'Hare Intl Airport on Cheapflights.
Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 8h 37m.
Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 8h 37m.
Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 3h 07m.
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Anonymous,Sep 2025
SEA - MKE
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$93 | Average$200 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$108 | Average$212 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$123 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$125 | Average$286 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$195 | Average$316 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$200 | Average$348 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$226 | Average$393 | FlexibilityNo cancel fee | On-time69% |