191 € 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 Airport to Chicago? If you want to travel next month, return fares start from 212 €. Find the lowest prices on one-way and return tickets right here.

Chicago.191 € per passenger.Departing Wed, 5 Aug, returning Mon, 10 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Wed, 5 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Portland.Price includes taxes and charges.From 191 €, select.

Chicago.196 € per passenger.Departing Fri, 10 Jul, returning Wed, 15 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Fri, 10 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 15 Jul, arriving in Portland.Price includes taxes and charges.From 196 €, select.

Chicago.209 € per passenger.Departing Thu, 28 May, returning Fri, 5 Jun.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Portland on Thu, 28 May, arriving in Chicago O'Hare International.Inbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri, 5 Jun, arriving in Portland.Price includes taxes and charges.From 209 €, select.

Chicago.211 € per passenger.Departing Tue, 26 May, returning Wed, 27 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Tue, 26 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 27 May, arriving in Portland.Price includes taxes and charges.From 211 €, select.

Chicago.212 € per passenger.Departing Sun, 13 Sep, returning Wed, 16 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Sun, 13 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 16 Sep, arriving in Portland.Price includes taxes and charges.From 212 €, select.

Chicago.212 € per passenger.Departing Tue, 2 Jun, returning Sat, 6 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Tue, 2 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 6 Jun, arriving in Portland.Price includes taxes and charges.From 212 €, select.

Chicago.213 € per passenger.Departing Thu, 30 Jul, returning Thu, 6 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Thu, 30 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 6 Aug, arriving in Portland.Price includes taxes and charges.From 213 €, select.

Chicago.214 € per passenger.Departing Mon, 29 Jun, returning Sat, 4 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Portland on Mon, 29 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 4 Jul, arriving in Portland.Price includes taxes and charges.From 214 €, select.

Chicago.259 € per passenger.Departing Tue, 11 Aug, returning Wed, 19 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Tue, 11 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 19 Aug, arriving in Portland.Price includes taxes and charges.From 259 €, select.

Chicago.260 € per passenger.Departing Tue, 13 Oct, returning Tue, 20 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Tue, 13 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 20 Oct, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Wed, 10 Jun, returning Sat, 13 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Wed, 10 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 13 Jun, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Tue, 25 Aug, returning Wed, 2 Sep.Return flight with United.Outbound direct flight with United departs from Portland on Tue, 25 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 2 Sep, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Wed, 24 Jun, returning Wed, 8 Jul.Return flight with United.Outbound direct flight with United departs from Portland on Wed, 24 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 8 Jul, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Fri, 29 May, returning Fri, 29 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Fri, 29 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 29 May, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Tue, 1 Sep, returning Tue, 8 Sep.Return flight with United.Outbound direct flight with United departs from Portland on Tue, 1 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 8 Sep, arriving in Portland.Price includes taxes and charges.From 260 €, select.

Chicago.260 € per passenger.Departing Sun, 24 May, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Sun, 24 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Portland.Price includes taxes and charges.From 260 €, select.

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 August.

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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 found	191 €
Cheapest month to fly	August
Average flight time	4 hrs, 1 min
Most popular airline	American Airlines
Average flights per week	226

Finding cheap flights from Portland to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Portland to Chicago?

The best price we found for a return flight from Portland to Chicago is 191 €. 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.

How long does it take to fly from Portland to Chicago?

4 hours and 1 minute is the average flight time from Portland to Chicago.

Which airlines fly direct from Portland to Chicago?

American Airlines, Qatar Airways and United fly direct from Portland to Chicago.

How many flights are there a week from Portland to Chicago?

As of May 2026, there are 226 flights per week flying from Portland to Chicago.

When is the cheapest time to fly from Portland to Chicago?

The cheapest month to fly from Portland to Chicago is usually August.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Portland Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 191 €.

Which upcoming date is cheapest to fly from Portland Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago on Wednesday, 5 August 2026.

Can I get a direct flight from Portland Airport to Chicago?

Yes – the average flight time is 4 hours and 1 minute.

How can I get the best flight deal from Portland Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In May, the average temperature is usually around 13°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.

Which is the cheapest airline to fly from Portland Airport to Chicago with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago.

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

The average duration of a direct flight from Portland International Airport to Chicago is 4 hours 30 minutes.
Chicago is two hours ahead of Portland, where Portland International Airport is located. Chicago follows the UTC-6 timezone.
Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) is the most traveled route, with 51 weekly flights to pick from. If you have things to do before heading off, the last flight from PDX to ORD is with United Airlines at 23:59. Opt for the first departure operated by American Airlines at 06:32 if you want to get on your way earlier.
For a relaxed start to your PDX to Chicago flight, allow plenty of time to check in and find your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the general rule.
Travelling during a peak time such as July? School holidays and other high seasons can mean longer lines at check-in and security. Play it safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.
Direct Portland International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll step off the plane.
Choose from a variety of carriers offering direct flights from Portland International Airport to Chicago. Reserve your trip with one of these:
Located around 10 kilometres from the centre of Portland, PDX can be reached in about 20 minutes by car, depending on traffic. The journey on public transport will take roughly 40 minutes.
Planning to catch an early flight from Portland International Airport to Chicago? Avoid rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these stays close to PDX:
83% of flights departing from Portland International Airport touch down at their destination on schedule. Given its strong on-time performance, delays are unlikely when taking off from PDX.
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 found for a one-way Portland International Airport to Chicago flight is 91 €. The cheapest price for a return flight is 191 €. Bear in mind fares can change due to availability at the time of booking.
Booking in advance is often the key to finding a cheap flight from PDX to Chicago. Fares tend to rise as seats fill up, so the closer your departure date, the more expensive your ticket may be.
If you can be flexible with your trip dates, try using the 'Whole month' search tool. It'll find the cheapest price across each month when looking for a Portland International Airport to Chicago ticket.
There's no need to check in daily to find out if fares have dropped when you create a Price Alert. We'll update you the moment there's an extra saving on cheap flights from PDX to Chicago.
Select your preferred arrival and departure 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

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It takes about 30 minutes to reach the centre driving.
It'll take around 45 minutes if you're travelling by public transport.
Consider staying in a hotel near ORD if you're coming in on a late flight from Portland International Airport to Chicago. Check in to one of these options and make your first night all about catching up on rest:
Secure the lowest price by booking your ride from Chicago O'Hare International Airport around four weeks in advance of your flight from PDX to Chicago.
The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

The centre of Chicago is about 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Portland International Airport to Chicago has hit the runway and you've navigated your way to arrivals, the drive should be around 25 minutes.
If you're catching public transport, it'll take about 30 minutes.
Place the 'Do not disturb' sign on your door and relax at a hotel close to MDW. Here are a few options where you can check in after your PDX to Chicago flight:
Snap up a deal by securing your ride from MDW four weeks ahead of time. You can also expect to have a greater selection of vehicles.
You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Hop off your flight from Portland International Airport to Chicago and go straight to your hotel or jump right into sightseeing. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to reach by car.
The journey takes around 2 hours when travelling by public transport.
If you don't want to make your way into the centre, choose a hotel near RFD. Settle in at one of these stays after your PDX to Chicago flight:
Rental companies sometimes offer deals on early bookings, so reserve your ride from RFD well ahead of your flight from Portland International Airport to Chicago. A bit of planning goes a long way in savings.
Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Portland International Airport to Chicago, while July is the busiest. Choose the best time to go to Chicago based on whether you like a laid-back vibe or a more bustling atmosphere.
Book a Portland International Airport to Chicago plane ticket with a departure in July if you want to visit the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).
Look for cheap tickets from PDX to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Check out these hotels after locking in your flight from Portland International Airport to Chicago:
All great adventures should include a little sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are attractions you won't want to skip in Chicago.

Explore more of the United States

Columbus is just one of the many places in the United States waiting to be explored after you've seen Chicago. Around 451 kilometres away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Experience the best of this destination with a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.