MDW - PWM

$90 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 8/31. 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

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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Flights 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

Tue, Jul 1 - Fri, Jul 4
Delta Logo
9:24 am - 4:10 pmMDW-PWM
5h 46m1 stop
Delta Logo
11:44 am - 5:40 pmPWM-MDW
6h 56m1 stop
$217Delta
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Tue, Jul 1 - Fri, Jul 4
Delta Logo
9:24 am - 4:10 pmMDW-PWM
5h 46m1 stop
Delta Logo
2:05 pm - 9:45 pmPWM-MDW
8h 40m2 stops
$222Delta
Find Deal
Tue, Jul 1 - Fri, Jul 4
Delta Logo
1:09 pm - 11:30 pmMDW-PWM
9h 21m2 stops
Delta Logo
2:05 pm - 9:45 pmPWM-MDW
8h 40m2 stops
$227Delta
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Tue, Sep 16 - Sat, Sep 20
Southwest Logo
6:25 am - 1:00 pmMDW-PWM
5h 35m1 stop
Southwest Logo
4:50 pm - 6:25 pmPWM-MDW
2h 35mnonstop
$241Southwest
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Sat, Sep 13 - Sun, Sep 14
Southwest Logo
12:50 pm - 4:05 pmMDW-PWM
2h 15mnonstop
Southwest Logo
7:55 pm - 9:30 pmPWM-MDW
2h 35mnonstop
$245Southwest
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Wed, Sep 3 - Tue, Sep 9
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
6:00 am - 1:36 pmPWM-MDW
8h 36m1 stop
$251Delta
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Tue, Aug 19 - Sat, Aug 23
Southwest Logo
2:55 pm - 10:25 pmMDW-PWM
6h 30m1 stop
Southwest Logo
4:50 pm - 6:25 pmPWM-MDW
2h 35mnonstop
$255Southwest
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Sat, Aug 23 - Sat, Aug 30
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
Delta Logo
11:28 am - 9:12 pmPWM-MDW
10h 44m2 stops
$256Delta
Find Deal
Wed, Sep 17 - Thu, Sep 25
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
Southwest Logo
10:35 am - 12:05 pmPWM-MDW
2h 30mnonstop
$259Southwest
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Sun, Sep 14 - Sat, Sep 20
Southwest Logo
7:10 pm - 10:25 pmMDW-PWM
2h 15mnonstop
Southwest Logo
5:45 am - 1:35 pmPWM-MDW
8h 50m2 stops
$260Southwest
Find Deal
Useful Info

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 Monday, as it's usually the priciest day. When flying back from Portland, Thursday is the cheapest day to fly and Saturday 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.

No, with an average price for the route of $368, prices are generally cheapest when you fly direct.

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Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$90
Best time to beat the crowds with an average 51% drop in price.
Most popular time to fly and prices are also 14% lower on average.
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 $90 for a one-way ticket and $217 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 Embraer 175 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • On which days can I fly direct from Chicago Midway Airport to Portland?

    There are nonstop flights from Chicago Midway Airport to Portland on a daily basis.

  • 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $259 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Portland?

Find which airlines fly direct from Chicago Midway Airport to Portland Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Portland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Portland to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

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 4287 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

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)

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