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
280 USD for flights from Portland to Chicago leaving on 10/28/2017 and returning on 12/1/2017
Low 1 USD
280 USD
High 922 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 9 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 March and December.
The cheapest flights from Portland to Chicago are currently available between October and December.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Frontier Airlines and Delta Air Lines are the cheapest airlines to fly this route.
Spirit Airlines, Frontier Airlines and Delta Air Lines are the most popular choices flying from Portland to Chicago.
Impact on price (additional fees may apply)
Spirit Airlines
+6%
Frontier Airlines
+13%
Delta Air Lines
+18%
Major US Carrier
+22%
Virgin America
+27%
American Airlines
+29%
Best time to fly
Portland to Chicago flights are approximately 8% more expensive in the morning than in the afternoon.
Morning flights tend to be the most expensive.
Impact on price
Cheapest day
Sunday is normally the most expensive day to fly, whilst Wednesday tends to be the cheapest.
Cheapest day of week is typically Wednesday and the most expensive is typically Sunday.
Impact on price
Cheapest route
Fly Portland Intl - Midway for the best Portland to Chicago flight prices saving up to 1% on average.
Portland Intl - Midway tends to be 1% cheaper than Portland Intl - O'Hare Intl.
We scan 50 sites offering flights from Portland to Chicago to find all the best options.
Impact on price
Portland Intl-Midway
+0%
Portland Intl-O'Hare Intl
+3%
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: 169 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Salt Lake City Intl - O'Hare Intl, Portland Intl - Mccarran Intl - O'Hare Intl and Portland Intl - Los Angeles Intl - O'Hare Intl.
You can fly from Portland Intl to Chicago indirect via Salt Lake City Intl, Mccarran Intl or Los Angeles Intl.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Portland
Return trip
Aug 23 - Aug 31
168 USD
FaregeekUSDOM
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Aug 23 - Aug 30
197 USD
FaregeekUSDOM
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Aug 23 - Aug 27
198 USD
FaregeekUSDOM
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Aug 29 - Aug 31
101 USD
KiwiUS
PDX PDX
3h 48min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Aug 25 - Aug 27
211 USD
FlightNetworkUS
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Aug 24 - Aug 24
279 USD
EDreamsUS
PDX PDX
4h 13min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Sep 7 - Sep 11
251 USD
KissAndFlyUS
PDX PDX
5h 53min
1 stop
CHI CHI
CHI CHI
6h 43min
1 stop
PDX PDX
Return trip
Sep 8 - Sep 12
266 USD
CheapBestFares
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
4h 24min
Direct
PDX PDX
Return trip
Sep 10 - Sep 20
300 USD
OmegaTravelUS
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
9h 29min
1 stop
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Aug 23 - Aug 29
110 USD
FlightNetworkUS
CHI CHI
4h 31min
Direct
PDX PDX
PDX PDX
3h 48min
Direct
CHI CHI
Return trip
Aug 23 - Aug 30
128 USD
FaregeekUSDOM
CHI CHI
4h 31min
Direct
PDX PDX
PDX PDX
3h 48min
Direct
CHI CHI
Return trip
Aug 23 - Aug 28
164 USD
FlightNetworkUS
CHI CHI
4h 31min
Direct
PDX PDX
PDX PDX
3h 48min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Thursday, Thursday, August 17, 2017

29°C
19°C

Friday, Friday, August 18, 2017

28°C
18°C

Saturday, Saturday, August 19, 2017

26°C
21°C

Sunday, Sunday, August 20, 2017

29°C
22°C

Monday, Monday, August 21, 2017

30°C
23°C

Tuesday, Tuesday, August 22, 2017

31°C
23°C

Wednesday, Wednesday, August 23, 2017

29°C
22°C

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
-1%
Chicago
3.95 USD
Cappuccino is 0.6% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
12.86 USD
-16%
Chicago
14.96 USD
Meal is 16% more expensive in Chicago than Portland
MILK
1 liter
Portland
2.98 USD
%
Chicago
2.98 USD
Milk is 0% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.5 USD
10%
Chicago
2.25 USD
Bus is 9.9% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
11.97 USD
-4%
Chicago
12.47 USD
movie theater is 4.2% more expensive in Chicago than Portland
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