Portland to Chicago Flights

Portland to Chicago Flight Info

Peak season for travel

November
£53

Cheapest return ticket price

£197
Portland(PDX) ⇒ Chicago(MDW)

Cheapest direct flight price

£114
Portland(PDX) ⇒ Chicago(ORD)

Frequently Asked Questions

  • When are flight tickets from Portland (PDX) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Portland to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Portland (PDX) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £198.
  • How long does it take to fly from Portland (PDX) to Chicago (CHI)?

    It takes about 4 hours 1 minute to fly from Portland (PDX) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 13km, by taxi about 30 minutes.
  • What are the most popular airlines that fly from Portland (PDX) to Chicago (CHI)?

    Airlines with flights from Portland (PDX) to Chicago (CHI): Alaska Airlines, American Airlines, Finnair, British Airways, Aer Lingus, Gulf Air and Iberia.
  • What's the most popular airline for non-stop flights from Portland (PDX) to Chicago (CHI)?

    United Airlines operates 232 non-stop flights from Portland (PDX) to Chicago (CHI).
  • How many airports are there in Chicago (CHI)?

  • What are some travel guidelines for Chicago during the COVID19 pandemic?

    Entry restrictions and flight schedule changes and cancellations are frequently updated and subject to change. If you plan to travel to Chicago, please obtain the most updated information from the airline you plan to book your travels with. You can also refer to COVID19 Country/Region Entry Restrictions for more information.
  • Which airlines offer free date changes for flights to this city during the COVID19 pandemic?

    There are no airlines with flights to this city that provide this service. Please use this information as a reference only and confirm with the airline prior to booking.

Portland (PDX) to Chicago (CHI) Flight Schedule

Flight info.
Departure
Arrival
Weekly Schedule
United Airlines

00:38

PDX

06:24

ORD

Portland to ChicagoSMTWTFSSearch
United Airlines

00:54

PDX

06:48

ORD

Portland to Chicago-------Search
United Airlines

00:56

PDX

06:50

ORD

Portland to Chicago-------Search
American Airlines

06:40

PDX

12:42

ORD

Portland to ChicagoSMTWTFSSearch
Finnair

06:50

PDX

12:56

ORD

Portland to Chicago------SSearch
Aer Lingus

07:00

PDX

13:03

ORD

Portland to ChicagoSMTWTFSSearch
United Airlines

07:11

PDX

13:00

ORD

Portland to ChicagoS------Search
Alaska Airlines

10:05

PDX

16:10

ORD

Portland to ChicagoSMTWTFSSearch
Alaska Airlines

10:30

PDX

16:35

ORD

Portland to ChicagoSMTWTFSSearch
United Airlines

10:55

PDX

16:49

ORD

Portland to ChicagoSMTWTFSSearch
Lufthansa

11:02

PDX

16:58

ORD

Portland to ChicagoS------Search
United Airlines

11:07

PDX

16:59

ORD

Portland to ChicagoSMTWTFSSearch
Aer Lingus

11:12

PDX

17:06

ORD

Portland to ChicagoS-T-T-SSearch
Alaska Airlines

12:45

PDX

18:55

ORD

Portland to ChicagoSMTWTFSSearch
British Airways

13:35

PDX

19:40

ORD

Portland to ChicagoS--WT--Search
Alaska Airlines

13:40

PDX

19:40

ORD

Portland to ChicagoSMTWTFSSearch
Lufthansa

13:55

PDX

19:50

ORD

Portland to Chicago-M--T-SSearch
American Airlines

14:00

PDX

20:03

ORD

Portland to ChicagoS-TWTFSSearch
Aer Lingus

14:17

PDX

20:10

ORD

Portland to Chicago--T----Search
Alaska Airlines

16:55

PDX

22:55

ORD

Portland to ChicagoS------Search
Alaska Airlines

17:15

PDX

23:14

ORD

Portland to Chicago--T----Search
Alaska Airlines

17:55

PDX

23:56

ORD

Portland to Chicago--T----Search
United Airlines

23:25

PDX

05:12

ORD

Portland to ChicagoSMTWTFSSearch
United Airlines

23:30

PDX

05:14

ORD

Portland to ChicagoS----F-Search
American Airlines

23:52

PDX

05:50

ORD

Portland to ChicagoSMT-T-SSearch
Iberia

23:59

PDX

06:01

ORD

Portland to Chicago-------Search
Show less
  • Plan Your Trip from Portland (PDX) to Chicago (CHI)

    Chicago attracts thousands of visitors every year for both business and pleasure. Whether you’re taking a last-minute break or a much needed getaway, flights from Portland to Chicago on Trip.com can help you get there with ease. With Trip.com, you can browse popular airlines with flights to Chicago, check the best season to visit, and preview Chicago attractions before you arrive. With flight deals and exciting attractions waiting for you to explore in Chicago, the best time to book flights from Portland to Chicago is now! Planning a trip from Portland to Chicago is easy when you use Trip.com to help you make travel arrangements. Whether you are flying one-way, non-stop, or round-trip, you will find just the flight you need with us. If you want to lock in a great deal for your flights, go for a round-trip flight, if you need flexibility with your itinerary, book a one-way flight to Chicago. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online and on the go. Pack your travel accessories, make a must-see bucket list, and book your flight to Chicago on Trip.com today!

  • A Trip to Remember (PDX—CHI)

    Make your journey from Portland (PDX) to Chicago (CHI) a trip to remember by using Trip.com to view Chicago attractions before you arrive. Once you know what to do in Chicago, you can reserve and book in advance for the best travel experience possible. Planning ahead is the most effective way to ensure your whole travel experience goes smoothly. Whether you need help choosing the perfect restaurant, discovering the best places to try local flavors, or finding the most stunning views in town, Trip.com is with you every step of the way for your trip to Chicago.