MDW - PWM

$125 Find Cheap Flights from Chicago Midway Airport to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Portland departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$249
Southwest
Thu 6/4Sun 6/7
MDW - PWM • Non-stop
Cheapest one-way
$125
Southwest
Sun 6/7
MDW - PWM • Non-stop
Top airlines
Southwest
Cheapest • from $249 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Avoid delays
Southwest
Most punctual • 94% on-time
Afternoon flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
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We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Portland (MDW-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Portland

Thu, Jun 4 - Sun, Jun 7
Southwest Logo
6:55 pm - 10:10 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
6:45 am - 8:20 am
PWM
-
MDW
2h 35mnonstop
$249Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
7:00 pm - 12:05 am
MDW
-
PWM
4h 05m
1 stop
Southwest Logo
6:45 am - 8:20 am
PWM
-
MDW
2h 35mnonstop
$259Southwest
Thu, May 28 - Thu, Jun 4
Southwest Logo
2:10 pm - 11:25 pm
MDW
-
PWM
8h 15m
2 stops
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
$264Southwest
Fri, May 8 - Sun, May 10
Southwest Logo
9:00 am - 4:15 pm
MDW
-
PWM
6h 15m
1 stop
Southwest Logo
4:20 pm - 9:35 pm
PWM
-
MDW
6h 15m
1 stop
$269Southwest
Fri, May 8 - Sun, May 10
Southwest Logo
9:00 am - 4:15 pm
MDW
-
PWM
6h 15m
1 stop
Southwest Logo
5:30 am - 3:20 pm
PWM
-
MDW
10h 50m
2 stops
$274Southwest
Thu, Apr 9 - Sun, Apr 12
Southwest Logo
7:30 am - 2:10 pm
MDW
-
PWM
5h 40m
1 stop
Southwest Logo
4:20 pm - 12:20 am
PWM
-
MDW
9h 00m
1 stop
$275Southwest
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
7:30 am - 2:10 pm
MDW
-
PWM
5h 40m
1 stop
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
$279Southwest
Thu, May 28 - Sun, May 31
Southwest Logo
2:10 pm - 11:25 pm
MDW
-
PWM
8h 15m
2 stops
Southwest Logo
5:30 am - 3:20 pm
PWM
-
MDW
10h 50m
2 stops
$280Southwest
Thu, Jun 11 - Mon, Jun 15
Southwest Logo
7:00 pm - 12:05 am
MDW
-
PWM
4h 05m
1 stop
Southwest Logo
1:00 pm - 9:55 pm
PWM
-
MDW
9h 55m
1 stop
$285Southwest
Fri, Jun 19 - Fri, Jun 26
Southwest Logo
6:55 pm - 10:10 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
$288Southwest
Booking Insights

KAYAK's insights & trends for Midway to Portland flights

Get data-powered insights and trends into flights from Midway to Portland to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Portland?

The average price of all round-trip flights from Chicago Midway Airport to Portland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Portland, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Portland, Tuesday is the cheapest day to fly and Sunday is the most expensive.

Can I save money by flying with a layover from Chicago Midway Airport to Portland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $410 on average.

Find deals

Good to know

Cheapest flight$125
Flight from Chicago Midway Airport to Portland

When to book flights from Midway to Portland

Are your dates flexible? Find out the best times to travel from Midway to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Portland flights

  • What is the cheapest flight from Chicago Midway Airport to Portland?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland was $125 for a one-way ticket and $249 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Portland?

    No, a passport isn't needed to fly from Chicago Midway Airport to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Portland?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Portland is Portland.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Portland?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Portland flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Portland?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PWM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4320 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Everything you need to know for your flight from Midway to Portland

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Portland (PWM)