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 | $226 (Frontier) |
One-way from | $109 (United Airlines) |
Popular in | March |
Cheapest in | August |
Average price | $339 |
Good round-trip deal | $334 or less |
Good one-way deal | $177 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 12/7
11:59 pm-5:52 am
Nonstop3h 53m
Chicago O'Hare Intl
Tue 12/9
4:10 pm-6:45 pm
Nonstop4h 35m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 12/10
11:59 pm-5:52 am
Nonstop3h 53m
Chicago O'Hare Intl
Mon 12/15
7:37 pm-10:15 pm
Nonstop4h 38m
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 12/10
7:04 am-1:09 pm
Nonstop4h 05m
Chicago O'Hare Intl
Mon 12/15
8:00 am-1:50 pm
1 stop7h 50m
PortlandChicago
PDX - ORD
PDXORD
Portland
Mon 12/8
12:32 am-8:40 am
1 stop6h 08m
Chicago O'Hare Intl
Tue 12/16
7:20 am-12:40 pm
1 stop7h 20m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 12/9
12:32 am-8:40 am
1 stop6h 08m
Chicago O'Hare Intl
Tue 12/16
6:00 am-12:54 pm
1 stop8h 54m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 12/12
12:32 am-10:33 am
1 stop8h 01m
Chicago O'Hare Intl
Tue 12/16
7:20 am-12:40 pm
1 stop7h 20m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 1/16
11:59 pm-6:00 am
Nonstop4h 01m
Chicago O'Hare Intl
Tue 1/20
8:45 am-1:45 pm
1 stop7h 00m
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 2/27
8:40 am-5:50 pm
1 stop7h 10m
Chicago O'Hare Intl
Mon 3/2
2:05 pm-4:39 pm
Nonstop4h 34m
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/10
7:00 am-1:04 pm
Nonstop4h 04m
Chicago O'Hare Intl
Wed 3/11
2:05 pm-4:39 pm
Nonstop4h 34m
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 1/11
1:30 pm-11:53 pm
1 stop8h 23m
Chicago O'Hare Intl
Wed 1/14
7:30 am-12:44 pm
1 stop7h 14m
| 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 77 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 $256). 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 21% 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 Saturday evenings 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
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Entertainment
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Entertainment
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Entertainment
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Entertainment
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Entertainment
Comfort
Boarding
Food
Overall
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$280 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$123 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$284 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$194 | Average$321 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$322 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$224 | Average$385 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$404 | FlexibilityNo cancel fee | On-time63% |