Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

PDX - MDW

$69 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 5/21. 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 6/7
Fri 6/14

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 43,968,530 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)

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
8:07 am - 5:12 pmPDX-MDW
7h 05m1 stop
7:35 am - 4:38 pmMDW-PDX
11h 03m1 stop
$159Frontier
Find Deal
Tue, May 21 - Thu, May 30
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
$163Frontier
Find Deal
Thu, May 23 - Tue, May 28
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
7:05 am - 5:43 pmMDW-PDX
12h 38m1 stop
$164Frontier
Find Deal
Thu, May 23 - Tue, May 28
4:00 pm - 5:50 amPDX-MDW
11h 50m2 stops
5:11 am - 7:07 amMDW-PDX
27h 56m1 stop
$166Frontier
Find Deal
Sat, May 18 - Mon, May 20
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
$168Frontier
Find Deal
Thu, May 23 - Tue, May 28
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
10:01 pm - 11:58 pmMDW-PDX
27h 57m1 stop
$169Frontier
Find Deal
Thu, May 23 - Sat, Jun 1
8:07 am - 5:12 pmPDX-MDW
7h 05m1 stop
11:56 am - 10:07 pmMDW-PDX
12h 11m1 stop
$173Frontier
Find Deal
Tue, May 21 - Sat, Jun 22
12:49 am - 11:08 amPDX-MDW
8h 19m1 stop
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
$174Frontier
Find Deal
Wed, Jun 5 - Sun, Jun 9
6:15 am - 4:55 pmPDX-MDW
8h 40m1 stop
5:00 pm - 11:25 pmMDW-PDX
8h 25m1 stop
$287Delta
Find Deal
Sat, May 18 - Sat, May 25
6:15 am - 4:55 pmPDX-MDW
8h 40m1 stop
5:00 pm - 11:25 pmMDW-PDX
8h 25m1 stop
$297Delta
Find Deal
Sat, May 18 - 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.

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 ($69) and Delta ($124). The cheapest round-trip tickets were found on Frontier ($159) and Delta ($287).

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 56m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 25 flights. The most frequent day of departure is Tuesday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

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

$69
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 $69 for a one-way ticket and $159 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 $612 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 10793 reviews
7.4Food
8.0Entertainment
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

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.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

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.

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 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.

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 😕

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.

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.
5/21Tue
1 stopFrontier
7h 05mPDX-MDW
$69
5/23Thu
1 stopFrontier
28h 56mPDX-MDW
$75
5/23Thu
1 stopFrontier
28h 56mPDX-MDW
$79
6/5Wed
1 stopFrontier
8h 19mPDX-MDW
$87
6/11Tue
2 stopsFrontier
8h 52mPDX-MDW
$88
7/10Wed
1 stopDelta
7h 45mPDX-MDW
$124
5/26Sun
1 stopDelta
6h 07mPDX-MDW
$141
6/16Sun
2 stops
18h 19mPDX-MDW
$220
7/31Wed
2 stops
16h 42mPDX-MDW
$222
6/11Tue
1 stopVolaris
13h 23mPDX-MDW
$364

Search by stops

Search by airline

Search by price

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.
5/13Mon
multi-stopFrontier
8h 39mPDX-MDW
5/21Tue
multi-stopFrontier
12h 38mMDW-PDX
$173
5/13Mon
multi-stopFrontier
8h 39mPDX-MDW
5/21Tue
multi-stopFrontier
24h 10mMDW-PDX
$179
5/13Mon
multi-stopFrontier
23h 26mPDX-MDW
5/22Wed
multi-stopFrontier
27h 47mMDW-PDX
$243
5/12Sun
multi-stopFrontier
8h 39mPDX-MDW
5/18Sat
multi-stopFrontier
13h 10mMDW-PDX
$259
5/13Mon
multi-stopFrontier
8h 39mPDX-MDW
5/15Wed
multi-stopFrontier
27h 18mMDW-PDX
$275
5/12Sun
multi-stopFrontier
12h 20mPDX-MDW
5/15Wed
multi-stopFrontier
27h 18mMDW-PDX
$280
5/13Mon
multi-stopDelta
6h 07mPDX-MDW
5/15Wed
multi-stopDelta
10h 55mMDW-PDX
$465
5/13Mon
multi-stopDelta
6h 07mPDX-MDW
5/16Thu
multi-stopDelta
10h 55mMDW-PDX
$489
5/11Sat
multi-stopDelta
6h 07mPDX-MDW
5/18Sat
multi-stopDelta
8h 23mMDW-PDX
$600
5/11Sat
multi-stop
25h 33mPDX-MDW
5/17Fri
multi-stop
28h 11mMDW-PDX
$619

Search by stops

Search by airline

Search by price

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: