Beginning of main content

Cheap Flights from Portland to Chicago from $232

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap PDX to ORD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 18 - Tue, Oct 1
PDX
Portland
to
ORD
Chicago
$232

roundtrip

found 2 days ago

Open PDX to ORD flights search result page
Wed, Sep 11 - Sat, Sep 14
PDX
Portland
to
ORD
Chicago
$250

roundtrip

found 1 day ago

Open PDX to ORD flights search result page
Wed, Sep 18 - Sun, Sep 22
PDX
Portland
to
ORD
Chicago
$252

roundtrip

found 9 hours ago

Open PDX to ORD flights search result page
Tue, Sep 10 - Wed, Sep 11
PDX
Portland
to
ORD
Chicago
$254

roundtrip

found 4 days ago

Open PDX to ORD flights search result page
Wed, Sep 18 - Tue, Oct 8
PDX
Portland
to
ORD
Chicago
$255

roundtrip

found 2 days ago

Open PDX to ORD flights search result page
Wed, Sep 11 - Mon, Sep 16
PDX
Portland
to
ORD
Chicago
$257

roundtrip

found 1 day ago

Open PDX to ORD flights search result page
Tue, Oct 22 - Tue, Oct 29
PDX
Portland
to
ORD
Chicago
$258

roundtrip

found 1 hour ago

Open PDX to ORD flights search result page
Wed, Sep 4 - Wed, Sep 11
PDX
Portland
to
ORD
Chicago
$258

roundtrip

found 5 hours ago

Open PDX to ORD flights search result page
Tue, Oct 22 - Tue, Oct 29
PDX
Portland
to
ORD
Chicago
$259

roundtrip

found 1 hour ago

Open PDX to ORD flights search result page
Wed, Sep 11 - Mon, Sep 16
PDX
Portland
to
ORD
Chicago
$263

roundtrip

found 1 day ago

Open PDX to ORD flights search result page
Fri, Sep 6 - Wed, Sep 11
PDX
Portland
to
ORD
Chicago
$266

roundtrip

found 4 hours ago

Open PDX to ORD flights search result page
Tue, Oct 22 - Tue, Oct 29
PDX
Portland
to
ORD
Chicago
$267

roundtrip

found 1 hour ago

Open PDX to ORD flights search result page
Wed, Sep 25 - Sat, Oct 5
PDX
Portland
to
ORD
Chicago
$268

roundtrip

found 15 hours ago

Open PDX to ORD flights search result page
Mon, Sep 16 - Sat, Sep 21
PDX
Portland
to
ORD
Chicago
$269

roundtrip

found 3 hours ago

Open PDX to ORD flights search result page
Wed, Sep 18 - Tue, Oct 8
PDX
Portland
to
ORD
Chicago
$271

roundtrip

found 2 days ago

Open PDX to ORD flights search result page
Tue, Aug 27 - Sat, Aug 31
PDX
Portland
to
ORD
Chicago
$281

roundtrip

found 2 days ago

Open PDX to ORD flights search result page
Fri, Sep 6 - Wed, Sep 11
PDX
Portland
to
ORD
Chicago
$291

roundtrip

found 4 hours ago

Open PDX to ORD flights search result page
Thu, Aug 22 - Mon, Aug 26
PDX
Portland
to
ORD
Chicago
$332

roundtrip

found 3 hours ago

Open PDX to ORD flights search result page
Mon, Oct 28 - Fri, Nov 8
PDX
Portland
to
ORD
Chicago
$611

roundtrip

found 2 hours ago

Open PDX to ORD flights search result page

Portland to Chicago route information

Origin Airport Portland Intl.
Destination Airport O'Hare Intl.
Airlines Serving Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, United
Flight Price $232
Distance 1,734 mi

Chicago

MDW-Midway Intl.

$283.51

Top Routes from Portland

Top Routes to Chicago

Cheap PDX to ORD Flights

  • Question : Which airline has the least delays from Portland to Chicago?
    Answer : Booking with Virgin America means you will arrive to Chicago approximately the time you were supposed to. In fact, this timely airline has a 100% on-time average. Of course, it never hurts to be prepared. If you’re on Delta Air Lines, be sure to sign up for the delay notifications to stay up to date with your flight’s status.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Portland to Chicago is on Wednesday. So, if you would like to save a little cash on your next vacation look for flights on Wednesday.
  • Question : How long is the flight from PDX to ORD?
    Answer : If you're able to take the direct flight (which is offered by United Airlines), you will be able to leave PDX at 11:10 PM PDT and get to ORD at 4:52 AM CDT (three hours and 42 minutes). Remember, there is a time change of two hours.
  • Question : How much is a plane ticket to Chicago (ORD) from Portland (PDX)?
    Answer : Cost can range from $252 to $1,436, prices for PDX to ORD change less than most routes in the United States. Prices are usually less the further out you book.
  • Question : What is the cheapest airline flying from Portland to Chicago?
    Answer : Spirit Airlines is the leader in keeping costs low for their passengers over the next three months. Bookings are being made at just $252 and, when compared to the more expensive bookings of $1,436, it's a terrific bargain.
  • Question : What is the cheapest day to fly to Chicago?
    Answer : As of May 20th, the best day for deals to Chicago (ORD) is Jun 3rd. It cost $252, which is 30% below the average price to book the same route.
  • Question : Can I change the date of my flight?
    Answer : Yes, you can change your departure date. If you would like to save a little cash in doing so, the cheapest day to fly in June is Wednesday.