CA $164 Cheap Flights from Portland (PWM) to Chicago (MDW)

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Cheap flights from Portland (PWM) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $164 for one-way flights and CA $336 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Flight from Portland to Chicago (PWM - MDW) route information
Origin airport
Portland Intl. Jetport
Destination airport
Midway Intl.
Roundtrip price
CA $335
Distance
1427 km
Average flight time
4 hours 25 mins

Portland to Chicago Flights

The easy way to book your flights from Portland to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Portland whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are Southwest Airlines nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Portland to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Portland Intl. Jetport, PWM to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Portland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Portland currently is just CA $336 rising to CA $445.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Portland 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Portland Intl. Jetport to Midway Intl. Airport (MDW)?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Portland Intl. Jetport Airport (PWM) and Midway Airport start from CA $336. Book ASAP to get the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from PWM to Midway Airport?
When it comes to cancellation fees, each airline has its own terms and conditions. If you decide to cancel your getaway, head to our Customer Service Portal.
How do I find cheap flights from Portland Intl. Jetport Airport (PWM) to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Portland Intl. Jetport to Midway Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Portland Intl. Jetport Airport (PWM) to Midway Intl. Airport (MDW)?
Forget about a movie marathon on this flight — it’s only 1,450 kilometers from Portland to Chicago. Find your seat, enjoy the in-flight service and you’ll be touching down before you know it.
Which airlines fly direct from PWM to MDW?
Southwest Airlines (WN) will fly you from Portland Intl. Jetport Airport (PWM) to Chicago Airport safely and reliably. Choose from 21 flights each month along this route.
Are Portland Intl. Jetport Airport (PWM) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Portland Intl. Jetport to Midway Intl. Airport (MDW) last minute could be your ticket to a cheap deal. However, it could end up costing you a whole lot more! If you’d rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.
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