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 4/6/2017 and returning on 5/5/2017
Low 108 USD
294 USD
High 507 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Portland — Chicago is approximately 47 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 November and December.
The cheapest flights from Portland to Chicago are currently available between April and May.
Impact on price
Cheapest airline
According to our data, Frontier Airlines, Spirit Airlines and Southwest Airlines are the cheapest airlines to fly this route.
Frontier Airlines, Spirit Airlines and Southwest Airlines are the most popular choices flying from Portland to Chicago.
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.
Morning flights tend to be the most expensive.
Impact on price
Cheapest day
Friday is normally the most expensive day to fly, whilst Monday tends to be the cheapest.
Cheapest day of week is typically Monday and the most expensive is typically Friday.
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 40 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: 135 PER WEEK
Popular non-direct routes for this connection are Portland Intl - Denver Intl - Midway, Portland Intl - Detroit Metro - Midway and Portland Intl - Mccarran Intl - O'Hare Intl.
You can fly from Portland Intl to Chicago indirect via Denver Intl, Detroit Metro 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
Feb 10 - Feb 13
228 USD
GotoGateUSMob
PDX PDX
3h 53min
Direct
CHI CHI
CHI CHI
4h 34min
Direct
PDX PDX
Return trip
Feb 4 - Feb 5
260 USD
ExpediaCOM
PDX PDX
4h 4min
Direct
CHI CHI
CHI CHI
4h 43min
Direct
PDX PDX
Return trip
Feb 13 - Feb 17
299 USD
FlyFarUS
PDX PDX
3h 49min
Direct
CHI CHI
CHI CHI
4h 48min
Direct
PDX PDX

Go right away

Last minute flights from Portland to Chicago
Return trip
Jan 25 - Jan 31
228 USD
KiwiUS
PDX PDX
12h 55min
1 stop
CHI CHI
CHI CHI
12h 45min
1 stop
PDX PDX
Return trip
Jan 25 - Jan 28
250 USD
KiwiUS
PDX PDX
12h 21min
1 stop
CHI CHI
CHI CHI
12h 45min
1 stop
PDX PDX
Return trip
Jan 27 - Jan 29
258 USD
KiwiUS
PDX PDX
9h 35min
1 stop
CHI CHI
CHI CHI
17h 50min
1 stop
PDX PDX

Go for less - experience more

Cheap flights from Portland to Chicago
Return trip
Feb 7 - Feb 9
216 USD
OneTravel
PDX PDX
20h 21min
1 stop
CHI CHI
CHI CHI
12h 58min
1 stop
PDX PDX
Return trip
Feb 10 - Feb 13
228 USD
GotoGateUSMob
PDX PDX
3h 53min
Direct
CHI CHI
CHI CHI
4h 34min
Direct
PDX PDX
Return trip
Feb 13 - Feb 14
240 USD
ExpediaCOM
PDX PDX
14h 21min
2 stops
CHI CHI
CHI CHI
20h 53min
2 stops
PDX PDX

Coming or going?

Cheap flights from Chicago to Portland
Return trip
Jan 24 - Feb 7
207 USD
ExpediaCOM
CHI CHI
12h 45min
1 stop
PDX PDX
PDX PDX
14h 26min
2 stops
CHI CHI
Return trip
Jan 24 - Feb 8
207 USD
ExpediaCOM
CHI CHI
12h 45min
1 stop
PDX PDX
PDX PDX
14h 31min
2 stops
CHI CHI
Return trip
Jan 24 - Feb 6
211 USD
KiwiUS
CHI CHI
12h 45min
1 stop
PDX PDX
PDX PDX
12h 48min
1 stop
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
3.84 USD
-3%
Chicago
3.97 USD
Cappuccino is 3.3% more expensive in Chicago than Portland
MEAL
Inexpensive
Portland
12.08 USD
-25%
Chicago
15.09 USD
Meal is 25% more expensive in Chicago than Portland
MILK
1 liter
Portland
3.44 USD
13%
Chicago
2.99 USD
Milk is 13% cheaper in Chicago than Portland
BUS
One-way ticket
Portland
2.52 USD
10%
Chicago
2.26 USD
Bus is 10% cheaper in Chicago than Portland
MOVIE THEATER
1 ticket
Portland
11.07 USD
-9%
Chicago
12.08 USD
movie theater is 9.1% more expensive in Chicago than Portland
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