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PDX - MDW

$90 Find cheap flights from Portland to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Midway departing on 5/12. 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
0 bags
Sun 5/26
Sun 6/2

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago, 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 Portland to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,335,567 times on KAYAK, and here is why:

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Cheap flight deals from Portland to Midway (PDX-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Midway 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 and deals for you by selecting your travel dates.
Choose your dates
6:06 pm - 8:31 amPDX-MDW
12h 25m1 stop
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
$142Frontier
Find Deal
Sat, May 11 - Sat, May 18
6:06 pm - 8:31 amPDX-MDW
12h 25m1 stop
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
$144Frontier
Find Deal
Sat, May 11 - Sat, May 18
6:06 pm - 8:31 amPDX-MDW
12h 25m1 stop
5:30 am - 11:59 pmMDW-PDX
20h 29m1 stop
$145Frontier
Find Deal
Sat, May 11 - Mon, May 13
11:30 am - 10:09 pmPDX-MDW
8h 39m1 stop
4:18 pm - 3:10 pmMDW-PDX
24h 52m1 stop
$148Frontier
Find Deal
Mon, May 13 - Fri, May 17
7:54 pm - 5:50 amPDX-MDW
31h 56m2 stops
5:01 am - 6:48 amMDW-PDX
27h 47m1 stop
$151Frontier
Find Deal
Fri, May 17 - Wed, May 22
6:06 pm - 8:31 amPDX-MDW
12h 25m1 stop
7:35 am - 4:42 pmMDW-PDX
11h 07m1 stop
$153Frontier
Find Deal
Sat, May 11 - Thu, May 16
6:05 pm - 9:22 amPDX-MDW
13h 17m1 stop
10:00 pm - 3:54 pmMDW-PDX
19h 54m1 stop
$155Frontier
Find Deal
Tue, May 14 - Fri, Aug 16
9:40 pm - 10:36 amPDX-MDW
10h 56m1 stop
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
$161Frontier
Find Deal
Thu, May 16 - Tue, May 21
11:45 am - 10:01 pmPDX-MDW
8h 16m1 stop
2:15 pm - 8:05 pmMDW-PDX
7h 50m1 stop
$292Delta
Find Deal
Wed, May 8 - Tue, May 14
10:25 pm - 9:12 amPDX-MDW
8h 47m1 stop
11:59 am - 4:07 pmMDW-PDX
6h 08m1 stop
$300Delta
Find Deal
Tue, Aug 27 - Sat, Sep 7

Flights from Portland to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Portland to Midway 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 Portland to Chicago Midway Airport?

The average price of all flights from Portland to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Portland to Chicago Midway Airport, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

What is the cheapest month to fly from Portland to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Portland to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Portland to Chicago Midway Airport is January, where tickets cost $182 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $630 and $615 respectively.

How far in advance should I book a flight from Portland to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Portland to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Portland to Chicago Midway Airport, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

Which airlines provide the cheapest flights from Portland to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($90) and Delta ($108). The cheapest round-trip tickets were found on Frontier ($142) and Delta ($292).

How many flights are there between Portland and Chicago Midway Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Portland and lands in Chicago Midway Airport, with an average flight time of 4h 00m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 7 flights.

What’s the earliest departure time from Portland to Chicago Midway Airport?

Early birds can take the earliest flight from Portland at 6:30 am and will be landing in Chicago Midway Airport at 12:30 pm.

What’s the latest departure time from Portland to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Portland to Chicago Midway Airport jets off at 7:25 am and lands at 1:25 pm.

Good to know

Low season

February

High season

March

Cheapest flight

$90
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Portland to Chicago Midway Airport

When to book flights from Portland to Midway

Are your dates flexible? Find out the best times to travel from Portland to Midway 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 Portland to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Portland to Chicago Midway Airport was $90 for a one-way ticket and $142 for a round-trip.

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

    No

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

    When flying out of Portland you will be using Portland. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

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

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

  • Which is the best airline for flights from Portland to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Delta and Frontier. With an average price for the route of $665 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $268 and an overall rating of 6.3.

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

    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 Portland to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Portland 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 Portland to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Portland with another airline. Booking your flights between Portland and MDW 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 Portland to Chicago Midway Airport?

    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 Chicago Midway Airport from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Portland to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 3 airlines serving from Portland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Portland to Chicago. 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 Portland to Midway? 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
DeltaOverall score based on 10966 reviews
7.4food
8.6crew
8.0entertainment
8.2boarding
7.9comfort
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Portland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Portland to Chicago found on KAYAK in the last 72 hours.
5/12Sun
1 stopFrontier
8h 39mPDX-MDW
$90
8/19Mon
1 stopFrontier
11h 16mPDX-MDW
$91
5/9Thu
1 stopFrontier
8h 39mPDX-MDW
$94
5/17Fri
1 stopFrontier
11h 42mPDX-MDW
$95
5/5Sun
1 stopFrontier
8h 39mPDX-MDW
$99
5/30Thu
1 stopDelta
6h 07mPDX-MDW
$108
7/19Fri
1 stopDelta
7h 45mPDX-MDW
$119
5/31Fri
3 stopsWestJet
30h 40mPDX-MDW
$389
5/31Fri
3 stops
30h 40mPDX-MDW
$400
8/21Wed
2 stops
22h 12mPDX-MDW
$450

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Last minute flights from Portland to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Portland to Chicago that are departing in the next 10 days.
5/1Wed
multi-stopFrontier
19h 04mPDX-MDW
5/8Wed
multi-stopFrontier
20h 29mMDW-PDX
$193
4/29Mon
multi-stopFrontier
23h 26mPDX-MDW
5/6Mon
multi-stopFrontier
20h 29mMDW-PDX
$207
4/30Tue
multi-stopFrontier
13h 17mPDX-MDW
5/2Thu
multi-stopFrontier
10h 03mMDW-PDX
$208
4/30Tue
multi-stopFrontier
8h 39mPDX-MDW
5/4Sat
multi-stopFrontier
12h 16mMDW-PDX
$213
4/30Tue
multi-stopFrontier
8h 39mPDX-MDW
5/5Sun
multi-stopFrontier
12h 11mMDW-PDX
$217
4/27Sat
multi-stopFrontier
12h 25mPDX-MDW
4/30Tue
multi-stopFrontier
14h 04mMDW-PDX
$218
4/27Sat
multi-stopFrontier
12h 25mPDX-MDW
4/29Mon
multi-stopFrontier
26h 02mMDW-PDX
$219
4/27Sat
multi-stopFrontier
12h 25mPDX-MDW
5/1Wed
multi-stopFrontier
24h 01mMDW-PDX
$227
4/27Sat
multi-stopDelta
7h 47mPDX-MDW
4/28Sun
multi-stopDelta
7h 59mMDW-PDX
$650
4/28Sun
multi-stopDelta
7h 47mPDX-MDW
5/7Tue
multi-stopDelta
9h 56mMDW-PDX
$736

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Portland - Chicago Midway Airport Flights

Departure:

Portland (PDX)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Portland

Cabin classes: