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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 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
Tue 6/4
Tue 6/11

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 43,369,418 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
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
5:05 am - 11:43 pmMDW-PDX
20h 38m1 stop
$147Frontier
Find Deal
Thu, May 23 - Sat, Jun 1
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
5:01 am - 7:07 amMDW-PDX
28h 06m1 stop
$156Frontier
Find Deal
Thu, May 23 - Mon, Jun 3
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
8:55 pm - 6:54 pmMDW-PDX
23h 59m2 stops
$161Frontier
Find Deal
Thu, May 23 - Thu, May 30
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
$162Frontier
Find Deal
Wed, May 15 - Tue, May 21
10:12 pm - 11:54 amPDX-MDW
11h 42m1 stop
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
$164Frontier
Find Deal
Fri, May 17 - Tue, May 21
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
5:01 am - 6:48 amMDW-PDX
27h 47m1 stop
$167Frontier
Find Deal
Sat, May 18 - Wed, May 22
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
5:01 am - 6:48 amMDW-PDX
27h 47m1 stop
$168Frontier
Find Deal
Wed, May 15 - Wed, May 22
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$170Frontier
Find Deal
Fri, Sep 6 - Wed, Sep 11
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
7:10 pm - 11:25 pmMDW-PDX
6h 15m1 stop
$221Delta
Find Deal
Thu, May 30 - Tue, Jun 4
12:50 am - 10:31 amPDX-MDW
7h 41m1 stop
10:11 am - 7:01 pmMDW-PDX
10h 50m1 stop
$226Delta
Find Deal
Fri, Oct 25 - Wed, Oct 30

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 ($147) and Delta ($221).

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

Each day, there are between 1 and 4 nonstop flights that take off from Portland and land in Chicago Midway Airport, with an average flight time of 3h 57m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 16 flights. The most frequent day of departure is Tuesday, when 25% of all weekly flights depart. The fewest flights depart on a Saturday.

How long does a flight from Portland to Chicago Midway Airport take?

The average nonstop flight takes 3h 55m, covering a distance of 1,746 miles.

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 $147 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 $647 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 6.2.

  • 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 10826 reviews
8.6Crew
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

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.

10.0 ExcellentBranton, May 2024AVL - ATL
Read more about Delta reviews

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.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

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.

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

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

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.

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
$85
5/21Tue
1 stopFrontier
7h 05mPDX-MDW
$89
5/21Tue
1 stopFrontier
7h 05mPDX-MDW
$90
9/9Mon
1 stopFrontier
12h 03mPDX-MDW
$91
5/30Thu
1 stopDelta
6h 07mPDX-MDW
$108
10/11Fri
1 stopDelta
7h 50mPDX-MDW
$124
5/30Thu
2 stops
24h 18mPDX-MDW
$194
7/4Thu
3 stops
24h 22mPDX-MDW
$312
5/31Fri
3 stopsWestJet
30h 40mPDX-MDW
$416
7/2Tue
1 stopVolaris
13h 23mPDX-MDW
$477

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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.
5/10Fri
multi-stopFrontier
17h 50mPDX-MDW
5/11Sat
multi-stopFrontier
12h 16mMDW-PDX
$193
5/10Fri
multi-stopFrontier
17h 50mPDX-MDW
5/13Mon
multi-stopFrontier
20h 29mMDW-PDX
$207
5/7Tue
multi-stopFrontier
8h 39mPDX-MDW
5/14Tue
multi-stopFrontier
20h 29mMDW-PDX
$254
5/7Tue
multi-stopFrontier
8h 39mPDX-MDW
5/13Mon
multi-stopFrontier
20h 29mMDW-PDX
$268
5/10Fri
multi-stopFrontier
23h 21mPDX-MDW
5/12Sun
multi-stopFrontier
12h 11mMDW-PDX
$298
5/7Tue
multi-stopFrontier
13h 17mPDX-MDW
5/8Wed
multi-stopFrontier
12h 11mMDW-PDX
$318
5/7Tue
multi-stopFrontier
8h 39mPDX-MDW
5/10Fri
multi-stopFrontier
12h 21mMDW-PDX
$328
5/10Fri
multi-stopFrontier
23h 21mPDX-MDW
5/12Sun
multi-stopFrontier
12h 11mMDW-PDX
$331
5/8Wed
multi-stopDelta
7h 08mPDX-MDW
5/13Mon
multi-stopDelta
6h 15mMDW-PDX
$455
5/8Wed
multi-stopDelta
7h 08mPDX-MDW
5/14Tue
multi-stopDelta
6h 15mMDW-PDX
$578

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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: