When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 16 days in advance, which can save you up to 124% on flights from Portland to Illinois compared to booking the week you need them. Waiting 16 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $528. For sooner than that we have options available in the next 3 days from $743.
Our data shows that January tends to be the cheapest month to fly to Illinois from Portland. Users have commonly found prices around $377 for the month, but tickets can be as low as $149. Due to multiple factors, prepare for potentially higher prices in June.
When flying from Portland to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$118 - $287
Route
Depart
Return
Price
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Sat 5/4
1 stop12h 25m
Chicago Midway
Wed 5/8
1 stop27h 46m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Sat 5/4
1 stop12h 25m
Chicago Midway
Wed 5/8
1 stop27h 46m
PortlandChicago Midway
PDX - MDW
PDXMDW
Portland
Tue 5/7
1 stop13h 17m
Chicago Midway
Wed 5/15
1 stop27h 18m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Wed 5/8
1 stop14h 35m
Chicago O'Hare Intl
Tue 5/14
1 stop10h 41m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Fri 6/7
Nonstop4h 07m
Chicago O'Hare Intl
Sun 6/9
Nonstop4h 27m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 5/21
Nonstop4h 06m
Chicago O'Hare Intl
Sat 6/22
Nonstop4h 28m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Thu 6/6
1 stop7h 49m
Chicago O'Hare Intl
Tue 6/18
1 stop8h 35m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Tue 5/7
Nonstop4h 21m
Chicago O'Hare Intl
Fri 5/10
Nonstop4h 34m
PortlandChicago O'Hare Intl
PDX - ORD
PDXORD
Portland
Fri 5/31
Nonstop3h 58m
Chicago O'Hare Intl
Wed 6/5
Nonstop4h 28m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
4%of flight departures | Early morningMidnight to 6 am |
---|---|
63%of flight departures | Morning6 am to noon |
25%of flight departures | AfternoonNoon to 6 pm |
8%of flight departures | Evening6 pm to midnight |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Portland to Illinois. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Illinois from Portland.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Portland to Illinois, users can toggle the no change fees filter when performing a flight search.
Of course! You can now track prices for flights from Portland to Illinois and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.