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
294 USD for flights from Portland to Chicago leaving on 12/31/2017 and returning on 2/2/2018
Low 97 USD
294 USD
High 922 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 58 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 December and February.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Frontier Airlines and Major US Carrier are the cheapest airlines to fly this route.
Spirit Airlines, Frontier Airlines and Major US Carrier are the most popular choices flying from Portland to Chicago.
Impact on price (additional fees may apply)
Spirit Airlines
+4%
Frontier Airlines
+9%
Major US Carrier
+11%
Delta Air Lines
+12%
Virgin America
+22%
Alaska Airlines
+25%
Best time to fly
Portland to Chicago flights are approximately 6% 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 Tuesday tends to be the cheapest.
Cheapest day of week is typically Tuesday 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 0% on average.
Portland Intl - Midway tends to be 0% cheaper than Portland Intl - O'Hare Intl.
We scan 48 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
+0%
Direct flights
There are direct flights from Portland Intl to Chicago all week with a flight time of 3 hours 48 minutes.
Direct flights available: 121 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Salt Lake City Intl - O'Hare Intl, Portland Intl - Sky Harbor Intl - O'Hare Intl and Portland Intl - Seattle Tacoma - Mccarran Intl - O'Hare Intl.
Stop-off cities for indirect flights from Portland Intl to Chicago include Salt Lake City Intl, Sky Harbor 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
Nov 22 - Nov 28
371 USD
CheapestFareNow
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 35min
Direct
PDX PDX
Return trip
Nov 20 - Nov 26
425 USD
BargainAirTicket
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 35min
Direct
PDX PDX
Return trip
Nov 22 - Nov 26
509 USD
CheapestFareNow
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 29min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Nov 3 - Nov 6
220 USD
ExploreTripDom
PDX PDX
17h 20min
1 stop
CHI CHI
CHI CHI
9h 8min
1 stop
PDX PDX
Return trip
Nov 2 - Nov 5
300 USD
ExploreTripDom
PDX PDX
9h 27min
1 stop
CHI CHI
CHI CHI
8h 9min
1 stop
PDX PDX
Return trip
Oct 26 - Oct 29
335 USD
FlyFarUS
PDX PDX
3h 57min
Direct
CHI CHI
CHI CHI
15h 53min
1 stop
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Nov 7 - Nov 14
168 USD
ExploreTripDom
PDX PDX
26h 34min
1 stop
CHI CHI
CHI CHI
20h 48min
1 stop
PDX PDX
Return trip
Nov 5 - Nov 8
192 USD
ExploreTripDom
PDX PDX
9h 36min
1 stop
CHI CHI
CHI CHI
12h 7min
1 stop
PDX PDX
Return trip
Nov 5 - Nov 10
220 USD
ExploreTripDom
PDX PDX
21h 20min
1 stop
CHI CHI
CHI CHI
9h 8min
1 stop
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Oct 26 - Nov 2
271 USD
OmegaTravelUS
CHI CHI
4h 28min
Direct
PDX PDX
PDX PDX
3h 57min
Direct
CHI CHI
Return trip
Oct 23 - Oct 25
305 USD
EDreamsUS
CHI CHI
12h 7min
1 stop
PDX PDX
PDX PDX
9h 27min
1 stop
CHI CHI
Return trip
Oct 23 - Oct 24
352 USD
ExploreTripDom
CHI CHI
4h 27min
Direct
PDX PDX
PDX PDX
21h 54min
1 stop
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Wednesday, Wednesday, October 18, 2017

17°C
12°C

Thursday, Thursday, October 19, 2017

18°C
12°C

Friday, Friday, October 20, 2017

21°C
15°C

Saturday, Saturday, October 21, 2017

22°C
15°C

Sunday, Sunday, October 22, 2017

16°C
12°C

Monday, Monday, October 23, 2017

17°C
12°C

Tuesday, Tuesday, October 24, 2017

12°C
8°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
3.95 USD
1%
Chicago
3.91 USD
Cappuccino is 0.9% cheaper in Chicago than Portland
MEAL
Inexpensive
Portland
12.01 USD
-25%
Chicago
15.02 USD
Meal is 25% more expensive in Chicago than Portland
MILK
1 liter
Portland
2.91 USD
-4%
Chicago
3.03 USD
Milk is 4% more expensive in Chicago than Portland
BUS
One-way ticket
Portland
2.51 USD
10%
Chicago
2.25 USD
Bus is 10% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
12.01 USD
-2%
Chicago
12.26 USD
movie theater is 2.1% more expensive in Chicago than Portland
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