Flights from Portland to Chicago

Search and find cheap flights from Portland to Chicago (United States, North America)
Search and find cheap flights from Portland to Chicago (United States, North America)

Looking for the best tickets for Portland to Chicago?

Look no more. We’ve gone through the latest 503,199 fares to bring you all the insights you could possibly want.
Expect to pay
249 USD for flights from Portland to Chicago leaving on 5/31/2017 and returning on 7/7/2017
Low 94 USD
249 USD
High 844 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 47 days to departure.
Normally the best deals on Portland to Chicago flights are available 2 to 4 months prior to departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Portland is January and February. Most expensive are November and December.
Currently the cheapest days to fly this route are between May and July.
Impact on price
Cheapest airline
According to our data, Frontier Airlines, Spirit Airlines and Southwest Airlines are the cheapest airlines to fly this route.
Popular airlines for this route are Frontier Airlines, Spirit Airlines and Southwest Airlines.
Impact on price (additional fees may apply)
Frontier Airlines
+13%
Spirit Airlines
+17%
Southwest Airlines
+19%
Major US Carrier
+22%
Delta Air Lines
+23%
Alaska Airlines
+23%
Best time to fly
Portland to Chicago flights are approximately 5% more expensive in the morning than in the afternoon.
It's generally cheaper to take afternoon flights from Portland to Chicago.
Impact on price
Cheapest day
Cheapest day of week is typically Monday and the most expensive is typically Friday.
Friday is normally the most expensive day to fly, whilst Monday tends to be the cheapest.
Impact on price
Cheapest route
Fly Portland Intl - Midway for the best Portland to Chicago flight prices saving up to 0% on average.
Of the possible routes between Portland and Chicago best prices tend to be found on Portland Intl - Midway.
We've got 41 booking sites supporting this and nearby routes.
Impact on price
Portland Intl-Midway
+0%
Portland Intl-O'Hare Intl
+1%
Direct flights
There are direct flights from Portland Intl to Chicago all week with a flight time of 3 hours 44 minutes.
Direct flights available: 125 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Albuquerque Intl - Midway, Portland Intl - Mccarran Intl - O'Hare Intl and Portland Intl - Saint Paul Intl - Midway.
Stop-off cities for indirect flights from Portland Intl to Chicago include Albuquerque Intl, Mccarran Intl and Saint Paul Intl.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Portland
Return trip
Mar 26 - Mar 30
482 USD
Flightsbank
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX
Return trip
Apr 2 - Apr 9
492 USD
Flightsbank
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 21min
Direct
PDX PDX
Return trip
Mar 31 - Apr 2
549 USD
Flightsbank
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Apr 6 - Apr 9
333 USD
KiwiUS
PDX PDX
12h 57min
1 stop
CHI CHI
CHI CHI
22h 5min
1 stop
PDX PDX
Return trip
Mar 27 - Mar 29
453 USD
KiwiUS
PDX PDX
13h 40min
1 stop
CHI CHI
CHI CHI
13h 3min
1 stop
PDX PDX
Return trip
Mar 24 - Mar 27
681 USD
FlyFarUS
PDX PDX
13h 40min
1 stop
CHI CHI
CHI CHI
17h 34min
1 stop
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Apr 12 - Apr 16
268 USD
GotoGateUSMob
PDX PDX
5h 31min
1 stop
CHI CHI
CHI CHI
8h 2min
1 stop
PDX PDX
Return trip
Apr 13 - Apr 18
268 USD
CFEDreamsUS
PDX PDX
11h 51min
1 stop
CHI CHI
CHI CHI
12h 10min
1 stop
PDX PDX
Return trip
Apr 7 - Apr 10
315 USD
ExploreTripDom
PDX PDX
8h 30min
1 stop
CHI CHI
CHI CHI
4h 26min
Direct
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Mar 24 - Mar 31
414 USD
PaylessFlights
CHI CHI
4h 30min
Direct
PDX PDX
PDX PDX
3h 54min
Direct
CHI CHI
Return trip
Mar 24 - Mar 27
420 USD
FlightNetworkUS
CHI CHI
7h 50min
1 stop
PDX PDX
PDX PDX
6h 29min
1 stop
CHI CHI
Return trip
Mar 24 - Apr 1
469 USD
JustFly
CHI CHI
12h 14min
1 stop
PDX PDX
PDX PDX
13h 40min
1 stop
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

So what's it going to cost once you're in Chicago

Compare the costs of everyday items in Portland and Chicago
CAPPUCCINO
Regular
Portland
3.86 USD
-3%
Chicago
3.96 USD
Cappuccino is 2.5% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
11.99 USD
-26%
Chicago
15.05 USD
Meal is 26% more expensive in Chicago than Portland
MILK
1 liter
Portland
3.28 USD
12%
Chicago
2.88 USD
Milk is 12% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.49 USD
10%
Chicago
2.25 USD
Bus is 9.5% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
10.98 USD
-10%
Chicago
12.04 USD
movie theater is 9.6% more expensive in Chicago than Portland
Feedback