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PDX - MDW

$85 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 6/5. 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
Sat 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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

 
These are the cheapest deals for flights from Portland to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Portland to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Midway.

Recent one-way flight deals from Portland to Midway

Only flying one-way? Below are some of the best one-way flight deals from Portland to Midway found on KAYAK recently.

Recent last minute flight deals from Portland to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Portland to Midway.

Recent direct flight deals from Portland to Midway

The latest deals for direct flights from Portland to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Portland to Midway

Find recent round-trip train or bus tickets from Portland to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:36 am - 1:49 pmPDX-MDW
11h 13m1 stop
10:41 pm - 6:45 amMDW-PDX
10h 04m1 stop
$169Frontier
Find Deal
Mon, May 27 - Thu, Jun 6
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
6:00 am - 11:49 pmMDW-PDX
19h 49m1 stop
$170Frontier
Find Deal
Wed, May 29 - Tue, Jun 4
4:40 pm - 5:14 amPDX-MDW
10h 34m1 stop
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
$171Frontier
Find Deal
Thu, Jun 6 - Sat, Jun 8
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
5:01 am - 11:35 pmMDW-PDX
20h 34m1 stop
$172Frontier
Find Deal
Wed, May 29 - Mon, Jun 3
12:48 am - 9:06 pmPDX-MDW
18h 18m1 stop
5:55 am - 11:49 pmMDW-PDX
19h 54m1 stop
$173Frontier
Find Deal
Fri, May 31 - Wed, Jun 5
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$174Frontier
Find Deal
Fri, Sep 6 - Mon, Sep 9
12:49 am - 1:09 pmPDX-MDW
10h 20m1 stop
5:05 am - 11:56 pmMDW-PDX
20h 51m1 stop
$175Frontier
Find Deal
Mon, Jun 10 - Sun, Jun 16
12:49 am - 12:00 pmPDX-MDW
9h 11m1 stop
8:58 pm - 9:42 pmMDW-PDX
26h 44m1 stop
$176Frontier
Find Deal
Tue, Jun 4 - Fri, Jun 7
4:00 pm - 5:50 amPDX-MDW
11h 50m2 stops
5:55 am - 11:49 pmMDW-PDX
19h 54m1 stop
$177Frontier
Find Deal
Sat, Jun 1 - Wed, Jun 5
6:15 am - 4:55 pmPDX-MDW
8h 40m1 stop
6:00 am - 12:49 pmMDW-PDX
8h 49m1 stop
$337Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5
12:49 am - 11:08 amPDX-MDW
8h 19m1 stop
$85Frontier
Find Deal
Wed, Jun 5
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$87Frontier
Find Deal
Tue, May 28
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$89Frontier
Find Deal
Tue, May 28
6:02 pm - 5:21 amPDX-MDW
9h 19m2 stops
$90Frontier
Find Deal
Sat, Jun 8
4:40 pm - 5:14 amPDX-MDW
10h 34m1 stop
$91Frontier
Find Deal
Thu, Jun 6
11:15 pm - 8:38 amPDX-MDW
7h 23m1 stop
$108Delta
Find Deal
Fri, Jul 12
12:50 am - 8:41 amPDX-MDW
5h 51m1 stop
$124Delta
Find Deal
Thu, Sep 19
11:59 pm - 7:40 pmPDX-MDW
17h 41m2 stops
Sun, Aug 4
6:30 pm - 7:40 pmPDX-MDW
23h 10m2 stops
Thu, Aug 1
8:15 am - 1:09 pmPDX-MDW
26h 54m3 stops
$508WestJet
Find Deal
Wed, Aug 21
8:07 am - 5:12 pmPDX-MDW
7h 05m1 stop
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
$185Frontier
Find Deal
Tue, May 21 - Sat, Jun 22
12:43 am - 1:49 pmPDX-MDW
11h 06m1 stop
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
$190Frontier
Find Deal
Mon, May 20 - Sat, Jun 22
8:07 am - 11:09 amPDX-MDW
25h 02m1 stop
5:40 am - 8:45 amMDW-PDX
29h 05m1 stop
$195Frontier
Find Deal
Tue, May 21 - Sat, Jun 22
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
9:10 pm - 10:04 pmMDW-PDX
26h 54m1 stop
$212Frontier
Find Deal
Tue, May 21 - Wed, May 29
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
5:01 am - 11:43 pmMDW-PDX
20h 42m1 stop
$213Frontier
Find Deal
Sat, May 18 - Wed, May 29
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:01 am - 11:43 pmMDW-PDX
20h 42m1 stop
$224Frontier
Find Deal
Tue, May 21 - Wed, May 29
10:48 pm - 7:55 amPDX-MDW
7h 07m1 stop
6:00 am - 12:49 pmMDW-PDX
8h 49m1 stop
$640Delta
Find Deal
Sat, May 18 - Tue, May 21
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
5:47 pm - 11:54 pmMDW-PDX
8h 07m2 stops
$673Delta
Find Deal
Tue, May 21 - Wed, May 29
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
5:47 pm - 11:54 pmMDW-PDX
8h 07m2 stops
$853Delta
Find Deal
Tue, May 21 - Wed, May 29
2:00 pm - 11:02 amPDX-MDW
19h 02m3 stops
2:15 pm - 1:10 pmMDW-PDX
24h 55m3 stops
$2,091WestJet
Find Deal
Fri, May 17 - Sun, May 19

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 October, where tickets cost $257 on average. On the other hand, the most expensive months are January and February, where the average cost of tickets is $527 and $453 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 30 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 ($85) and Delta ($108). The cheapest round-trip tickets were found on Frontier ($169) and Delta ($337).

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

Each day, there are between 3 and 4 nonstop flights that take off from Portland and land in Chicago Midway Airport, with an average flight time of 3h 55m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 27 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Early birds can take the earliest flight from Portland at 5:00 am and will be landing in Chicago Midway Airport at 10:55 am.

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 6:50 pm and lands at 12:45 am.

Good to know

Low season

February

High season

September

Cheapest flight

$85
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly and prices are also 22% lower on average.
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 $85 for a one-way ticket and $169 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 $595 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 $266 and an overall rating of 6.2.

  • 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 10673 reviews
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

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.

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

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.
6/5Wed
1 stopFrontier
8h 19mPDX-MDW
$85
5/28Tue
1 stopFrontier
8h 21mPDX-MDW
$87
5/28Tue
1 stopFrontier
8h 21mPDX-MDW
$89
6/8Sat
2 stopsFrontier
9h 19mPDX-MDW
$90
6/6Thu
1 stopFrontier
10h 34mPDX-MDW
$91
7/12Fri
1 stopDelta
7h 23mPDX-MDW
$108
9/19Thu
1 stopDelta
5h 51mPDX-MDW
$124
8/4Sun
2 stops
17h 41mPDX-MDW
$221
8/1Thu
2 stops
23h 10mPDX-MDW
$235
8/21Wed
3 stopsWestJet
26h 54mPDX-MDW
$508

Search by stops

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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.
5/21Tue
multi-stopFrontier
7h 05mPDX-MDW
6/22Sat
multi-stopFrontier
12h 19mMDW-PDX
$185
5/20Mon
multi-stopFrontier
11h 06mPDX-MDW
6/22Sat
multi-stopFrontier
12h 19mMDW-PDX
$190
5/21Tue
multi-stopFrontier
25h 02mPDX-MDW
6/22Sat
multi-stopFrontier
29h 05mMDW-PDX
$195
5/21Tue
multi-stopFrontier
8h 21mPDX-MDW
5/29Wed
multi-stopFrontier
26h 54mMDW-PDX
$212
5/18Sat
multi-stopFrontier
8h 36mPDX-MDW
5/29Wed
multi-stopFrontier
20h 42mMDW-PDX
$213
5/21Tue
multi-stopFrontier
8h 21mPDX-MDW
5/29Wed
multi-stopFrontier
20h 42mMDW-PDX
$224
5/18Sat
multi-stopDelta
7h 07mPDX-MDW
5/21Tue
multi-stopDelta
8h 49mMDW-PDX
$640
5/21Tue
multi-stopDelta
6h 07mPDX-MDW
5/29Wed
multi-stopDelta
8h 07mMDW-PDX
$673
5/21Tue
multi-stopDelta
6h 07mPDX-MDW
5/29Wed
multi-stopDelta
8h 07mMDW-PDX
$853
5/17Fri
multi-stopWestJet
19h 02mPDX-MDW
5/19Sun
multi-stopWestJet
24h 55mMDW-PDX
$2,091

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Portland - Chicago Midway Airport Flights

Departure:

Portland (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Portland

Cabin classes:

$737