$95 Cheap flights from Portland Intl. to Midway Intl. (PDX to MDW)

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

Amazing PDX to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $184 round trip and $95 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 28 - Sun, Sep 1
PDX
Portland
MDW
Chicago
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Aug 28 from Portland to Chicago, returning Sun, Sep 1, priced at $184 found 4 days ago
Wed, Jun 12 - Wed, Jun 19
PDX
Portland
MDW
Chicago
$185 Roundtrip, found 6 days ago
$185
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 12 from Portland to Chicago, returning Wed, Jun 19, priced at $185 found 6 days ago
Sat, May 25 - Sat, Jun 1
PDX
Portland
MDW
Chicago
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 25 from Portland to Chicago, returning Sat, Jun 1, priced at $187 found 5 days ago
Sat, Sep 14 - Sun, Sep 22
PDX
Portland
MDW
Chicago
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 14 from Portland to Chicago, returning Sun, Sep 22, priced at $188 found 4 days ago
Fri, May 31 - Thu, Jun 6
PDX
Portland
MDW
Chicago
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 31 from Portland to Chicago, returning Thu, Jun 6, priced at $189 found 5 days ago
Mon, Sep 2 - Wed, Sep 18
PDX
Portland
MDW
Chicago
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Sep 2 from Portland to Chicago, returning Wed, Sep 18, priced at $190 found 1 hour ago
Sat, May 25 - Sun, Jun 2
PDX
Portland
MDW
Chicago
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 25 from Portland to Chicago, returning Sun, Jun 2, priced at $191 found 5 days ago
Tue, Jun 4 - Thu, Jun 13
PDX
Portland
MDW
Chicago
$192 Roundtrip, found 12 hours ago
$192
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Jun 4 from Portland to Chicago, returning Thu, Jun 13, priced at $192 found 12 hours ago
Fri, May 31 - Fri, Jun 7
PDX
Portland
MDW
Chicago
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 31 from Portland to Chicago, returning Fri, Jun 7, priced at $193 found 5 days ago
Wed, Jun 5 - Sat, Jun 8
PDX
Portland
MDW
Chicago
$195 Roundtrip, found 12 hours ago
$195
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Jun 5 from Portland to Chicago, returning Sat, Jun 8, priced at $195 found 12 hours ago

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from PDX Airport to MDW?
If you’re not a big fan of stopovers, it’s smart to lock in your flight from Portland Intl. Airport (PDX) to Chicago Airport well in advance of your departure. Southwest Airlines is the only air carrier that operates direct flights on this route.
How long is the flight from PDX Airport to Chicago Airport?
If you’re flying from Portland Airport to Chicago Airport, you can expect the trip to take around 5 hours and 40 minutes. If this is longer than you anticipated, why not take advantage of it? Read about where you’re going, get some last-minute organizing done and have a decent rest before the adventure begins.
What is the flight distance from PDX to Chicago Airport?
Covering 1,750 mi between PDX and PDX calls for a glass of bubbly and a few good movies. Lean back, get comfortable and just enjoy the ride.
What airlines fly from PDX Airport to MDW?
Many savvy wanderers like traveling with Southwest Airlines (WN) from Portland Intl. Airport (PDX) to MDW. This reputable airline not only offers up to 43 flights per month, it also flies nonstop.
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.

 

Traveling From
Portland Intl.
Traveling To
Midway Intl.
Shortest Flight Time
8 hours 0 mins
Earliest Departure Time
6:30AM CDT
Latest Departure Time
6:30AM CDT
Lowest Flight Price
$184

Route Info

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


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


Discover our best flights from Portland PDX to Chicago MDW. 

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 Portland PDX to Chicago MDW at the right price  

Airfares to Chicago MDW from Portland PDX currently cost between $184 and $195. 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 Portland PDX to Chicago MDW 

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 Portland PDX to Chicago MDW on Travelocity starting at $95. Prices and availability subject to change. Additional terms may apply. 

 

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

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from PDX to take around 8 hour(s) 0 min(s).  

 

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

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from PDX. 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 Portland PDX to Chicago MDW today 

If you’re flexible about when you travel, August is usually the cheapest month to fly from Portland PDX to Chicago MDW. 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 Chicago MDW from Portland PDX 

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

 

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

*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.