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
282 USD for flights from Portland to Chicago leaving on 9/2/2017 and returning on 10/6/2017
Low 93 USD
282 USD
High 880 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 54 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 October. Most expensive are March and December.
The cheapest flights from Portland to Chicago are currently available between September and October.
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
+0%
Frontier Airlines
+7%
Delta Air Lines
+12%
Major US Carrier
+16%
Virgin America
+19%
Alaska Airlines
+20%
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
Saturday 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 Saturday.
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.
momondo compares flights to Chicago from Portland from 45 different sites.
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: 161 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Mccarran Intl - O'Hare Intl, Portland Intl - Los Angeles Intl - O'Hare Intl and Portland Intl - Seattle Tacoma - Mccarran Intl - O'Hare Intl.
You can fly from Portland Intl to Chicago indirect via Mccarran Intl, Los Angeles Intl or Seattle Tacoma.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Portland
Return trip
Jun 29 - Jul 3
300 USD
CFFlyFarUS
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
4h 17min
Direct
PDX PDX
Return trip
Jun 28 - Jul 4
335 USD
FlyFarUS
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Jun 29 - Jul 5
385 USD
OmegaTravelUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 24min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Jun 29 - Jul 3
300 USD
CFFlyFarUS
PDX PDX
3h 50min
Direct
CHI CHI
CHI CHI
4h 17min
Direct
PDX PDX
Return trip
Jun 30 - Jul 3
331 USD
CFFlyFarUS
PDX PDX
3h 55min
Direct
CHI CHI
CHI CHI
4h 17min
Direct
PDX PDX
Return trip
Jun 29 - Jun 30
463 USD
KiwiUS
PDX PDX
3h 54min
Direct
CHI CHI
CHI CHI
11h 39min
1 stop
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Jul 12 - Jul 19
254 USD
Cheapoair
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Jul 12 - Jul 17
254 USD
CFEDreamsUS
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX
Return trip
Jul 12 - Jul 26
255 USD
FlyingCOM
PDX PDX
4h 0min
Direct
CHI CHI
CHI CHI
4h 31min
Direct
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Jun 28 - Jul 3
238 USD
Cheapoair
CHI CHI
4h 17min
Direct
PDX PDX
PDX PDX
3h 52min
Direct
CHI CHI
Return trip
Jun 28 - Jul 5
254 USD
Cheapoair
CHI CHI
4h 17min
Direct
PDX PDX
PDX PDX
4h 0min
Direct
CHI CHI
Return trip
Jun 29 - Jul 4
318 USD
EDreamsUS
CHI CHI
4h 17min
Direct
PDX PDX
PDX PDX
3h 52min
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
3.94 USD
-1%
Chicago
3.96 USD
Cappuccino is 0.57% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
12.12 USD
-24%
Chicago
15.07 USD
Meal is 24% more expensive in Chicago than Portland
MILK
1 liter
Portland
3.18 USD
7%
Chicago
2.96 USD
Milk is 7.1% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.53 USD
11%
Chicago
2.26 USD
Bus is 11% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
11.36 USD
-6%
Chicago
12.06 USD
movie theater is 6.1% more expensive in Chicago than Portland
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