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

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Flights from Portland (PWM) to Chicago (MDW)
Origin airport
Portland Intl. Jetport
Destination airport
Midway Intl.
Distance
1427 km

Portland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Portland to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with PWM to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Portland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

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 . 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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