Cheap Flights from Portland to Chicago

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Flight deals from Portland to Chicago

Looking for a cheap last-minute deal or the best return flight from Portland to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Portland to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Portland to Chicago flights are currently cheapest in September.

Direct flights from Portland to Chicago

Alternative Portland to Chicago routes

Looking for the cheapest, fastest or easiest route from Portland to Chicago? You could fly into the following airports instead.

Portland to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,185
Cheapest month to flySeptember
Average flight time4 hrs, 2 mins
Most popular airlineAmerican Airlines
Average flights per week187

Finding cheap flights from Portland to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Portland to Chicago is R 2,337. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 1 minute is the average flight time from Portland to Chicago.
American Airlines, United and Qatar Airways fly direct from Portland to Chicago.
As of August 2025, there are 187 flights per week flying from Portland to Chicago.
The cheapest month to fly from Portland to Chicago is usually September.
If you're flying from Portland Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from R 2,337.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago on Saturday, 6 September 2025.
Yes – the average flight time is 4 hours and 1 minute.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

Travelling from Portland International Airport (PDX) to Chicago: what you need to know

  • The average time for a direct flight from Portland International Airport to Chicago is 4 hours 30 minutes.

  • Portland International Airport is located in Portland. Following the UTC-5 timezone, Chicago is two hours ahead of Portland.

  • The most popular route is from Portland International Airport (PDX) to O'Hare International Airport (ORD). There are 48 services every week between these two airports. If you want to take off as soon as possible, the earliest flight from PDX to ORD is the 06:32 American Airlines service. If you'd rather fly out later on, the last departure is at 23:59 with United Airlines.

  • To avoid missing your PDX to Chicago flight, leave plenty of time for things like check-in and baggage drop. Turning up two hours before international departures and an hour before domestic flights is the standard rule.

  • If you're heading away during a major holiday or another peak period, allow for even more time. A good rule is two hours ahead of domestic flights and up to four hours before international departures. Lines at check-in and security will be longer.

  • Start your trip at PDX and fly straight to O'Hare International Airport (ORD). That's where you can expect to touch down when searching for Portland International Airport to Chicago tickets.

  • Choose from a variety of airlines offering direct flights from Portland International Airport to Chicago. Book your journey with one of these:

  • PDX is about 10 kilometres from central Portland. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 20 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the travel time to be around 45 minutes.

  • Booked an early flight from Portland International Airport to Chicago? Avoid the last-minute rush to the airport (and catch some extra z's) by choosing one of these stays near PDX:

  • Portland International Airport gets high marks for its on-time performance. 83.65% of flights that take off from PDX reach their destination on time.

  • PDX is located at 7000 NE Airport Way.

How to find the cheapest flights from Portland International Airport (PDX) to Chicago

  • The lowest price we've seen for a one-way Portland International Airport to Chicago flight is R 1,185. The cheapest price for a return flight is R 2,337. Keep in mind fares can change due to availability at the time of booking.

  • Get cheap flights from PDX to Chicago by booking one month ahead. Based on our research, that's the best time for finding the biggest deals.

  • Plan your trip for May. That's the best month for scoring an incredible deal on Portland International Airport to Chicago tickets. If your travel dates are flexible, use the 'Whole month' tool to find the cheapest price across every month.

  • Locking in a cheap flight from PDX to Chicago is a breeze with Price Alerts. All you need to do is create one of these automatic notifications and we'll let you know when a better deal is available.

  • Choose your ideal departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Portland International Airport to Chicago by 'Best,' 'Cheapest' or 'Fastest.'

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're catching a cab or a ride-share, the drive will take roughly 35 minutes.

  • It typically takes 55 minutes to get there using public transport.

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Portland International Airport to Chicago. Check in to one of these accommodation options near ORD instead:

  • Begin your adventure by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and experience the lesser-explored corners of Chicago and beyond.

  • Booking your ride from O'Hare International Airport around four weeks ahead of your flight from PDX to Chicago can help you lock in the lowest rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is located around 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Portland International Airport to Chicago has hit the runway and you've made your way out of the airport, expect a drive of about 20 minutes.

  • The journey will take about 45 minutes on public transport.

  • You'll find some great places to call home for the night near MDW. Unwind and get cosy after your PDX to Chicago flight at one of these perfectly located options:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car simple. These trusted providers are located in or around the terminal and will have you on the road before long.

  • Secure your first choice, not your last resort. Securing your ride from MDW four weeks in advance often means lower prices and a greater selection of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Portland International Airport to Chicago and go straight to your hotel or start taking in the sights right away. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to drive there.

  • The journey will take you about 4 hours 15 minutes when travelling by public transport.

  • Enjoy a more relaxed start to your break by staying at a hotel near RFD after your PDX to Chicago flight. Rest up after a long day of travel or just give yourself time to find your footing in a new place at:

  • Be in the driver's seat of the next leg of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are reliable rental providers.

  • If you're hoping for a certain kind of vehicle, booking early increases your chances of snagging what you want. Book your ride from RFD a few weeks ahead of your flight from Portland International Airport to Chicago.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your travel dates before booking your flight from Portland International Airport to Chicago. The city comes alive in peak season, but hotel rates are generally higher and top attractions can get crowded. Go to Chicago in the low season if you want a more relaxed vibe.

  • When booking your Portland International Airport to Chicago flight ticket, think about the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you like cooler conditions, search for a cheap ticket from PDX to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • You've visited Chicago, now it's time to explore other corners of United States. Travel around 451 kilometres south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you on the go.

  • If you want to check out another great destination in United States, consider Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.