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
268 USD for flights from Portland to Chicago leaving on 7/1/2017 and returning on 8/4/2017
Low 90 USD
268 USD
High 853 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 55 days to departure.
Portland to Chicago flights are usually cheapest between 2 and 4 months before departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Portland is January and February. Most expensive are March and October.
Currently the cheapest days to fly this route are between July and August.
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
+7%
Spirit Airlines
+11%
Southwest Airlines
+17%
Alaska Airlines
+18%
Delta Air Lines
+18%
Major US Carrier
+20%
Best time to fly
Portland to Chicago flights are approximately 4% 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 Tuesday and the most expensive is typically Sunday.
Sunday is normally the most expensive day to fly, whilst Tuesday tends to be the cheapest.
Impact on price
Cheapest route
Fly Portland Intl - O'Hare Intl 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 - O'Hare Intl.
We've got 45 booking sites supporting this and nearby routes.
Impact on price
Portland Intl-O'Hare Intl
+0%
Portland Intl-Midway
+0%
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: 153 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Mccarran Intl - O'Hare Intl, Portland Intl - Saint Paul Intl - Midway and Portland Intl - Seattle Tacoma - Mccarran Intl - O'Hare Intl.
Stop-off cities for indirect flights from Portland Intl to Chicago include Mccarran Intl, Saint Paul Intl and Seattle Tacoma.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Portland
Return trip
Apr 27 - May 4
178 USD
Smartfares
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX
Return trip
Apr 27 - May 1
208 USD
FlyFarUS
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX
Return trip
Apr 27 - May 5
216 USD
KiwiUS
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 23min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Apr 27 - May 4
178 USD
Smartfares
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX
Return trip
Apr 27 - May 5
216 USD
KiwiUS
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 23min
Direct
PDX PDX
Return trip
Apr 27 - May 6
289 USD
OneTravel
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
May 11 - May 15
178 USD
Smartfares
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX
Return trip
May 10 - May 14
231 USD
Smartfares
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX
Return trip
May 11 - May 14
248 USD
EDreamsUS
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 16min
Direct
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Apr 27 - May 9
209 USD
FlyFarUS
CHI CHI
4h 16min
Direct
PDX PDX
PDX PDX
3h 55min
Direct
CHI CHI
Return trip
Apr 27 - May 1
271 USD
SkyToursUS
CHI CHI
4h 16min
Direct
PDX PDX
PDX PDX
3h 55min
Direct
CHI CHI
Return trip
Apr 27 - May 3
271 USD
SkyToursUS
CHI CHI
4h 16min
Direct
PDX PDX
PDX PDX
3h 55min
Direct
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
3.92 USD
-2%
Chicago
3.99 USD
Cappuccino is 1.7% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
11.95 USD
-26%
Chicago
15.04 USD
Meal is 26% more expensive in Chicago than Portland
MILK
1 liter
Portland
3.22 USD
8%
Chicago
2.96 USD
Milk is 8.1% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.49 USD
%
Chicago
2.51 USD
Bus is 0.44% more expensive in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
11.2 USD
-8%
Chicago
12.04 USD
movie theater is 7.5% more expensive in Chicago than Portland
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