$100 Cheap flights from Midway Intl. to Portland Intl. (MDW to PDX)

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Find The Best Dates To Fly from Midway Intl. to Portland Intl.

Compare Flight Prices from Chicago to Portland

Affordable Airfare Tickets from MDW to PDX Airport

The cheapest flights to Portland Intl. found within the past 7 days were $207 round trip and $100 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 7 - Fri, Jan 9
MDW
Chicago
PDX
Portland
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 7 from Chicago to Portland, returning Fri, Jan 9, priced at $207 found 3 days ago
Wed, Dec 10 - Sun, Dec 14
MDW
Chicago
PDX
Portland
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Portland, returning Sun, Dec 14, priced at $211 found 4 days ago
Thu, Feb 12 - Wed, Feb 18
MDW
Chicago
PDX
Portland
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from Chicago to Portland, returning Wed, Feb 18, priced at $217 found 2 days ago
Tue, Feb 10 - Tue, Feb 17
MDW
Chicago
PDX
Portland
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Feb 10 from Chicago to Portland, returning Tue, Feb 17, priced at $217 found 2 days ago
Wed, Dec 10 - Sun, Dec 14
MDW
Chicago
PDX
Portland
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 10 from Chicago to Portland, returning Sun, Dec 14, priced at $225 found 4 days ago
Thu, Feb 12 - Wed, Feb 18
MDW
Chicago
PDX
Portland
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from Chicago to Portland, returning Wed, Feb 18, priced at $226 found 2 days ago
Wed, Jan 7 - Fri, Jan 9
MDW
Chicago
PDX
Portland
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 7 from Chicago to Portland, returning Fri, Jan 9, priced at $227 found 3 days ago
Wed, Dec 10 - Sun, Dec 14
MDW
Chicago
PDX
Portland
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Portland, returning Sun, Dec 14, priced at $230 found 4 days ago
Wed, Feb 18 - Fri, Feb 20
MDW
Chicago
PDX
Portland
$236 Roundtrip, found 22 hours ago
$236
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Chicago to Portland, returning Fri, Feb 20, priced at $236 found 22 hours ago
Wed, Dec 10 - Wed, Dec 17
MDW
Chicago
PDX
Portland
$241 Roundtrip, found 23 hours ago
$241
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Portland, returning Wed, Dec 17, priced at $241 found 23 hours ago

Portland Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Unicorn Inn by OYO Portland

Unicorn Inn by OYO Portland

2.5 out of 5
Price was $359, price is now $296 per person
$296
per person
Dec 12 - Dec 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PDX)
Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Price was $505, price is now $394 per person
$394
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PDX)
Sentinel Hotel

Sentinel Hotel

5 out of 5
Price was $491, price is now $398 per person
$398
per person
Dec 12 - Dec 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PDX)
Hotel Lucia

Hotel Lucia

4 out of 5
Price was $445, price is now $360 per person
$360
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PDX)
Budget Inn Gladstone By OYO - Portland/Clackamas

Budget Inn Gladstone By OYO - Portland/Clackamas

2.5 out of 5
Price was $394, price is now $321 per person
$321
per person
Dec 12 - Dec 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PDX)
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Frequently asked questions

Can I catch a flight from MDW to PDX right now?
Ensure you check out the Covid-19 Travel Advisor to find out if there are any current quarantine requirements or travel advice reports in place in PDX when flying in from Chicago Airport.
Are there direct flights from Chicago Airport to Portland Intl. Airport (PDX)?
The only thing standing between you and your next extraordinary adventure is a single flight. Southwest Airlines is the only air carrier that sells direct tickets between MDW and PDX, so you may want to book ahead.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Portland Intl. Airport (PDX), please visit our Customer Service Portal.
How long is the flight from Midway Airport to Portland Intl. Airport (PDX)?
The travel time between Midway Intl. Airport (MDW) and Portland Airport is typically around 6 hours and 13 minutes. Make your journey comfortable by saving a few episodes on your tablet or laptop and enjoying them with your seat reclined.
What is the flight distance from Midway Airport to PDX Airport?
There's a flight distance of 1,750 mi separating MDW and Portland Airport. This is classified as a medium-haul flight. There'll be enough time to make the most of the in-flight entertainment and fit in a little sleep if you want to feel fresh on landing.
What airlines fly from Chicago Airport to PDX Airport?
Ready to lock in the airfare for your next big adventure? Want to get from Chicago to Portland in the shortest possible time? Take one of the 43 direct flights offered by Southwest Airlines every month, and you'll be landing before you can utter 'Are we there yet?'
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Alaska Airlines, Delta or United Airlines you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Chicago to Portland

 

Traveling From
Midway Intl.
Traveling To
Portland Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$207

Route Info

Flight path for flights from Chicago Midway International Airport to Portland International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
PDX - Portland International Airport
Distance:
1,756.00 miles


Discover our best flights from Chicago MDW to Portland PDX. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to Portland PDX at the right price  

Airfares to Portland PDX from Chicago MDW currently cost between $207 and $241. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to Portland PDX 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to Portland PDX on Travelocity starting at $100. Prices and availability subject to change. Additional terms may apply. 

 

Get to Portland PDX from Chicago MDW quicker with direct flights. 

Get to Portland faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to PDX from MDW to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to Portland PDX

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to PDX from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to Portland PDX today 

If you’re flexible about when you travel, January is usually the cheapest month to fly from Chicago MDW to Portland PDX. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Portland PDX from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to PDX from MDW have this option.  

 

Travel with confidence when you book flights to Portland PDX from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.