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$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 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
Fri 6/21
Fri 6/28

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 43,423,329 times on KAYAK, and here is why:

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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
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
11:26 am - 6:58 pmMDW-PDX
9h 32m1 stop
$176Frontier
Find Deal
Sun, Jun 2 - Wed, Jun 12
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:55 am - 11:52 pmMDW-PDX
19h 57m1 stop
$179Frontier
Find Deal
Sun, Jun 2 - Wed, Jun 12
12:35 am - 1:49 pmPDX-MDW
11h 14m1 stop
2:06 pm - 11:56 pmMDW-PDX
11h 50m1 stop
$180Frontier
Find Deal
Mon, Jun 3 - Tue, Jun 11
4:40 pm - 5:14 amPDX-MDW
10h 34m1 stop
5:55 am - 11:52 pmMDW-PDX
19h 57m1 stop
$181Frontier
Find Deal
Thu, Jun 6 - Wed, Jun 12
12:49 am - 12:00 pmPDX-MDW
9h 11m1 stop
5:05 am - 6:45 amMDW-PDX
27h 40m1 stop
$182Frontier
Find Deal
Tue, Jun 4 - Sun, Jun 9
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:05 am - 6:45 amMDW-PDX
27h 40m1 stop
$184Frontier
Find Deal
Sun, Jun 2 - Sun, Jun 9
6:02 pm - 5:21 amPDX-MDW
9h 19m2 stops
2:06 pm - 11:56 pmMDW-PDX
11h 50m1 stop
$185Frontier
Find Deal
Sat, Jun 8 - Tue, Jun 11
9:32 pm - 10:36 amPDX-MDW
11h 04m1 stop
5:01 am - 6:45 amMDW-PDX
27h 44m1 stop
$187Frontier
Find Deal
Sun, Jun 2 - Thu, Jun 13
4:40 pm - 5:14 amPDX-MDW
10h 34m1 stop
5:55 am - 11:56 pmMDW-PDX
20h 01m1 stop
$188Frontier
Find Deal
Thu, Jun 6 - Mon, Jun 10
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:55 am - 11:56 pmMDW-PDX
20h 01m1 stop
$189Frontier
Find Deal
Sun, Jun 2 - Mon, Jun 10
12:49 am - 11:08 amPDX-MDW
8h 19m1 stop
$90Frontier
Find Deal
Wed, Jun 5
12:48 am - 11:13 amPDX-MDW
8h 25m1 stop
$93Frontier
Find Deal
Fri, May 31
12:59 am - 11:12 amPDX-MDW
8h 13m1 stop
$94Frontier
Find Deal
Sat, Jun 8
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$95Frontier
Find Deal
Tue, May 28
4:40 pm - 5:14 amPDX-MDW
10h 34m1 stop
$96Frontier
Find Deal
Thu, Jun 6
10:55 pm - 8:44 amPDX-MDW
7h 49m1 stop
$108Delta
Find Deal
Sat, Sep 7
12:30 am - 11:27 amPDX-MDW
8h 57m1 stop
$144Delta
Find Deal
Fri, Jun 28
11:59 pm - 7:44 pmPDX-MDW
17h 45m2 stops
Sun, Jun 9
11:59 pm - 8:18 pmPDX-MDW
18h 19m2 stops
Thu, Jun 20
8:15 am - 6:36 pmPDX-MDW
32h 21m3 stops
$558WestJet
Find Deal
Sun, Jun 9
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
7:35 am - 4:06 pmMDW-PDX
10h 31m1 stop
$199Frontier
Find Deal
Sat, May 25 - Thu, May 30
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
9:10 pm - 10:04 pmMDW-PDX
26h 54m1 stop
$209Frontier
Find Deal
Sat, May 25 - Wed, May 29
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
8:55 pm - 6:54 pmMDW-PDX
23h 59m2 stops
$214Frontier
Find Deal
Sat, May 25 - Thu, May 30
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
5:01 am - 11:58 pmMDW-PDX
20h 57m1 stop
$218Frontier
Find Deal
Sat, May 25 - Sun, Jun 2
12:36 am - 5:12 pmPDX-MDW
14h 36m1 stop
7:35 am - 4:38 pmMDW-PDX
11h 03m1 stop
$224Frontier
Find Deal
Mon, May 27 - Thu, May 30
12:36 am - 5:12 pmPDX-MDW
14h 36m1 stop
7:40 am - 4:06 pmMDW-PDX
10h 26m1 stop
$229Frontier
Find Deal
Mon, May 27 - Sun, Jun 2
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
5:00 pm - 11:23 pmMDW-PDX
8h 23m1 stop
$302Delta
Find Deal
Mon, May 27 - Sat, Jun 1
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
7:10 pm - 11:25 pmMDW-PDX
6h 15m1 stop
$327Delta
Find Deal
Mon, May 27 - Fri, May 31
10:48 pm - 10:11 amPDX-MDW
9h 23m1 stop
7:10 pm - 11:25 pmMDW-PDX
6h 15m1 stop
$352Delta
Find Deal
Sat, May 25 - Fri, May 31
1:05 pm - 2:22 pmPDX-MDW
23h 17m3 stops
5:00 pm - 1:10 pmMDW-PDX
22h 10m3 stops
$1,473
Find Deal
Thu, May 23 - Sat, May 25

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.

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 25 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Wednesday.

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

$90
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 $90 for a one-way ticket and $176 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 $584 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 10585 reviews
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

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!!!!

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.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

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.

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
$90
5/31Fri
1 stopFrontier
8h 25mPDX-MDW
$93
6/8Sat
1 stopFrontier
8h 13mPDX-MDW
$94
5/28Tue
1 stopFrontier
8h 21mPDX-MDW
$95
6/6Thu
1 stopFrontier
10h 34mPDX-MDW
$96
9/7Sat
1 stopDelta
7h 49mPDX-MDW
$108
6/28Fri
1 stopDelta
8h 57mPDX-MDW
$144
6/9Sun
2 stops
17h 45mPDX-MDW
$190
6/20Thu
2 stops
18h 19mPDX-MDW
$202
6/9Sun
3 stopsWestJet
32h 21mPDX-MDW
$558

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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.
5/25Sat
multi-stopFrontier
8h 36mPDX-MDW
5/30Thu
multi-stopFrontier
10h 31mMDW-PDX
$199
5/25Sat
multi-stopFrontier
8h 36mPDX-MDW
5/29Wed
multi-stopFrontier
26h 54mMDW-PDX
$209
5/25Sat
multi-stopFrontier
8h 36mPDX-MDW
5/30Thu
multi-stopFrontier
23h 59mMDW-PDX
$214
5/25Sat
multi-stopFrontier
8h 36mPDX-MDW
6/2Sun
multi-stopFrontier
20h 57mMDW-PDX
$218
5/27Mon
multi-stopFrontier
14h 36mPDX-MDW
5/30Thu
multi-stopFrontier
11h 03mMDW-PDX
$224
5/27Mon
multi-stopFrontier
14h 36mPDX-MDW
6/2Sun
multi-stopFrontier
10h 26mMDW-PDX
$229
5/27Mon
multi-stopDelta
6h 07mPDX-MDW
6/1Sat
multi-stopDelta
8h 23mMDW-PDX
$302
5/27Mon
multi-stopDelta
6h 07mPDX-MDW
5/31Fri
multi-stopDelta
6h 15mMDW-PDX
$327
5/25Sat
multi-stopDelta
9h 23mPDX-MDW
5/31Fri
multi-stopDelta
6h 15mMDW-PDX
$352
5/23Thu
multi-stop
23h 17mPDX-MDW
5/25Sat
multi-stop
22h 10mMDW-PDX
$1,473

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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