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
286 USD for flights from Portland to Chicago leaving on 4/29/2017 and returning on 6/2/2017
Low 107 USD
286 USD
High 503 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 47 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 November and December.
Currently the cheapest days to fly this route are between April and June.
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 scan 42 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
+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: 138 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Seattle Tacoma - O'Hare Intl, Portland Intl - San Francisco Intl - O'Hare Intl and Portland Intl - Seattle Tacoma - Mccarran Intl - O'Hare Intl.
You can fly from Portland Intl to Chicago indirect via Seattle Tacoma, San Francisco Intl or Mccarran Intl.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Portland
Return trip
Mar 1 - Mar 3
265 USD
OmegaTravelUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 48min
Direct
PDX PDX
Return trip
Mar 9 - Mar 12
310 USD
OmegaTravelUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX
Return trip
Mar 10 - Mar 26
350 USD
OmegaTravelUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Mar 1 - Mar 6
195 USD
KiwiUS
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
13h 3min
1 stop
PDX PDX
Return trip
Feb 28 - Mar 7
203 USD
OneTravel
PDX PDX
9h 23min
1 stop
CHI CHI
CHI CHI
13h 3min
1 stop
PDX PDX
Return trip
Feb 22 - Feb 27
219 USD
Orbitz
PDX PDX
14h 21min
2 stops
CHI CHI
CHI CHI
20h 53min
2 stops
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Mar 8 - Mar 11
222 USD
EDreamsUS
PDX PDX
13h 10min
1 stop
CHI CHI
CHI CHI
17h 4min
1 stop
PDX PDX
Return trip
Mar 8 - Mar 12
281 USD
CheapTicketsDeal
PDX PDX
9h 2min
1 stop
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX
Return trip
Mar 9 - Mar 12
310 USD
OmegaTravelUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 30min
Direct
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Feb 22 - Feb 27
207 USD
ExploreTripDom
CHI CHI
16h 16min
1 stop
PDX PDX
PDX PDX
3h 49min
Direct
CHI CHI
Return trip
Feb 22 - Feb 26
320 USD
FlyFarUS
CHI CHI
4h 48min
Direct
PDX PDX
PDX PDX
5h 59min
1 stop
CHI CHI
Return trip
Feb 23 - Feb 26
373 USD
KissAndFlyUS
CHI CHI
8h 56min
1 stop
PDX PDX
PDX PDX
7h 50min
1 stop
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Tuesday, Tuesday, February 21, 2017

17°C
9°C

Wednesday, Wednesday, February 22, 2017

18°C
12°C

Thursday, Thursday, February 23, 2017

12°C
-4°C

Friday, Friday, February 24, 2017

17°C
3°C

Saturday, Saturday, February 25, 2017

3°C
-2°C

Sunday, Sunday, February 26, 2017

5°C
-1°C

Monday, Monday, February 27, 2017

6°C
2°C

Tuesday, Tuesday, February 28, 2017

12°C
7°C

Wednesday, Wednesday, March 1, 2017

10°C
0°C

Thursday, Thursday, March 2, 2017

6°C
1°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
3.86 USD
-4%
Chicago
4.01 USD
Cappuccino is 3.8% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
12.04 USD
-25%
Chicago
15.05 USD
Meal is 25% more expensive in Chicago than Portland
MILK
1 liter
Portland
3.41 USD
13%
Chicago
2.97 USD
Milk is 13% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.51 USD
%
Chicago
2.51 USD
Bus is 0% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
11.29 USD
-7%
Chicago
12.04 USD
movie theater is 6.7% more expensive in Chicago than Portland
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