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.
Round-trip from | $198 (Alaska Airlines) |
---|---|
One-way from | $113 (FlightHub) |
Popular in | March |
Cheapest in | January |
Average price | $317 |
Good round-trip deal | $250 or less |
Good one-way deal | $171 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 9/19
8:04 pm-4:49 am
1 stop6h 45m
Chicago O'Hare Intl
mié. 10/1
6:00 am-11:12 am
1 stop7h 12m
PortlandChicago
PDX - ORD
PDXORD
Portland
mié. 8/27
10:38 am-4:47 pm
Nonstop4h 09m
Chicago O'Hare Intl
dom. 8/31
7:00 am-9:24 am
Nonstop4h 24m
PortlandChicago
PDX - MDW
PDXMDW
Portland
mar. 8/26
1:30 pm-7:30 pm
Nonstop4h 00m
Chicago Midway
sáb. 8/30
2:10 pm-4:25 pm
Nonstop4h 15m
PortlandChicago
PDX - ORD
PDXORD
Portland
sáb. 9/6
1:24 pm-12:03 am
1 stop8h 39m
Chicago O'Hare Intl
mié. 9/10
2:07 pm-4:37 pm
Nonstop4h 30m
PortlandChicago
PDX - MDW
PDXMDW
Portland
sáb. 8/30
10:05 pm-9:36 am
1 stop9h 31m
Chicago Midway
mar. 9/23
1:43 pm-8:56 pm
1 stop9h 13m
PortlandChicago
PDX - ORD
PDXORD
Portland
sáb. 9/6
1:24 pm-12:03 am
1 stop8h 39m
Chicago O'Hare Intl
sáb. 9/20
6:20 am-12:27 pm
1 stop8h 07m
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 9/19
12:45 am-8:28 am
1 stop5h 43m
Chicago O'Hare Intl
mié. 9/24
5:30 pm-11:52 pm
1 stop8h 22m
PortlandChicago
PDX - ORD
PDXORD
Portland
lun. 8/11
3:10 pm-6:03 am
1 stop12h 53m
Chicago O'Hare Intl
mié. 8/13
7:00 am-11:30 am
1 stop6h 30m
PortlandChicago
PDX - ORD
PDXORD
Portland
mar. 8/26
8:15 am-4:45 pm
1 stop6h 30m
Chicago O'Hare Intl
sáb. 8/30
1:30 pm-8:35 pm
1 stop9h 05m
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 8/7
6:35 am-12:32 am
1 stop15h 57m
Chicago O'Hare Intl
dom. 8/10
9:56 pm-12:51 pm
1 stop16h 55m
Booking 84 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 $245). Flying from Portland to Chicago 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.
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 40% 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 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.
The most flights from PDX to CHI are scheduled on a Wednesday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
Las Vegas (LAS) – chosen by Cheapflights users on 55% of 1-stop itineraries from Portland to Chicago on Cheapflights.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $136.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 32m.
Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 30m.
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
Jonathan,Jul 2025
SEA - BOS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$96 | Average$176 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$108 | Average$219 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$123 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$178 | Average$292 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$187 | Average$337 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$218 | Average$328 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$224 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$249 | Average$437 | FlexibilityNo cancel fee | On-time63% |