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$91 Find cheap flights from Chicago Midway Airport to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Portland departing on 6/15. 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 Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, 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 Chicago to Portland, 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.

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

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

 
These are the cheapest deals for flights from Midway to Portland 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 Midway to Portland

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

Recent one-way flight deals from Midway to Portland

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

Recent last minute flight deals from Midway to Portland

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

Recent direct flight deals from Midway to Portland

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

Cheap bus & train deals from Midway to Portland

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

All round-trip flight deals to Portland

The cheapest plane tickets to Portland found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:00 pm - 3:54 pmMDW-PDX
19h 54m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$167Frontier
Find Deal
Mon, Sep 9 - Mon, Sep 23
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$168Frontier
Find Deal
Tue, Sep 10 - Wed, Sep 18
5:01 am - 11:43 pmMDW-PDX
20h 42m1 stop
7:43 am - 11:08 amPDX-MDW
25h 25m1 stop
$169Frontier
Find Deal
Wed, May 29 - Wed, Jun 5
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
12:52 am - 11:08 amPDX-MDW
8h 16m1 stop
$170Frontier
Find Deal
Sat, Jun 8 - Wed, Jun 12
6:00 am - 11:49 pmMDW-PDX
19h 49m1 stop
12:49 am - 11:47 amPDX-MDW
8h 58m1 stop
$172Frontier
Find Deal
Tue, Jun 4 - Fri, Jun 7
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$173Frontier
Find Deal
Fri, Sep 27 - Mon, Sep 30
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$174Frontier
Find Deal
Fri, Sep 6 - Mon, Sep 9
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
3:34 pm - 5:29 amPDX-MDW
11h 55m2 stops
$175Frontier
Find Deal
Sat, Jun 8 - Mon, Jun 10
5:01 am - 11:43 pmMDW-PDX
20h 42m1 stop
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
$176Frontier
Find Deal
Wed, May 29 - Sat, Jun 1
9:10 pm - 7:20 pmMDW-PDX
24h 10m2 stops
10:54 pm - 5:50 amPDX-MDW
28h 56m1 stop
$177Frontier
Find Deal
Tue, May 28 - Thu, May 30
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
$91Frontier
Find Deal
Sat, Jun 15
5:01 am - 6:48 amMDW-PDX
27h 47m1 stop
$95Frontier
Find Deal
Wed, May 29
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
$96Frontier
Find Deal
Sat, May 25
8:33 pm - 1:09 pmMDW-PDX
42h 36m3 stops
Mon, Jun 3
12:08 pm - 11:05 amMDW-PDX
24h 57m2 stops
Mon, Jun 3
7:20 pm - 11:35 pmMDW-PDX
6h 15m1 stop
$313Delta
Find Deal
Sun, Jul 21
2:15 pm - 8:05 pmMDW-PDX
7h 50m1 stop
$318Delta
Find Deal
Wed, May 29
9:46 am - 11:19 amMDW-PDX
27h 33m3 stops
$464WestJet
Find Deal
Wed, Jun 5
2:00 pm - 1:18 pmMDW-PDX
25h 18m3 stops
$530WestJet
Find Deal
Tue, Oct 15
10:41 pm - 9:00 pmMDW-PDX
24h 19m3 stops
$746Volaris
Find Deal
Tue, Jun 4
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
8:20 pm - 5:50 amPDX-MDW
31h 30m2 stops
$213Frontier
Find Deal
Sat, May 18 - Wed, May 22
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$219Frontier
Find Deal
Sat, May 18 - Tue, May 21
5:01 am - 11:58 pmMDW-PDX
20h 57m1 stop
8:20 pm - 5:50 amPDX-MDW
31h 30m2 stops
$252Frontier
Find Deal
Sun, May 19 - Wed, May 22
11:31 am - 9:22 pmMDW-PDX
11h 51m1 stop
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
$256Frontier
Find Deal
Fri, May 17 - Sat, May 18
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
12:48 am - 11:19 amPDX-MDW
8h 31m1 stop
$264Frontier
Find Deal
Sat, May 18 - Sun, May 19
11:31 am - 9:22 pmMDW-PDX
11h 51m1 stop
12:33 am - 11:09 amPDX-MDW
8h 36m1 stop
$265Frontier
Find Deal
Fri, May 17 - Sat, May 18
5:00 pm - 11:23 pmMDW-PDX
8h 23m1 stop
10:47 pm - 7:55 amPDX-MDW
7h 08m1 stop
$540Delta
Find Deal
Sat, May 18 - Wed, May 22
7:10 pm - 11:25 pmMDW-PDX
6h 15m1 stop
11:57 am - 10:01 pmPDX-MDW
8h 04m1 stop
$907Delta
Find Deal
Fri, May 17 - Mon, May 20
10:04 am - 12:15 pmMDW-PDX
28h 11m3 stops
6:29 pm - 9:52 amPDX-MDW
13h 23m1 stop
Fri, May 17 - Tue, May 21
9:46 am - 4:41 pmMDW-PDX
8h 55m2 stops
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
$1,782Delta
Find Deal
Sun, May 19 - Tue, May 21

Flights from Midway to Portland - Travel Insights & Trends

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

The average price of all flights from Chicago Midway Airport to Portland clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Portland on a Monday and more expensive on a Friday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Mondays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Portland, 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 Chicago Midway Airport to Portland is January, where tickets cost $313 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $418 and $418 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Portland, 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 Chicago Midway Airport to Portland, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 86 days before departure.

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

Each day, there are 4 nonstop flights that take off from Chicago Midway Airport and land in Portland, with an average flight time of 4h 20m. The most common departure time is 5:00 pm and most flights take off in the afternoon. Each week, there are 28 flights and there are the same amount of flights each day 4.

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

Early birds can take the earliest flight from Chicago Midway Airport at 8:10 am and will be landing in Portland at 10:30 am.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Portland jets off at 10:50 pm and lands at 1:10 am.

Good to know

Low season

January

High season

July

Cheapest flight

$91
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to Portland

When to book flights from Midway to Portland

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland was $91 for a one-way ticket and $167 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Delta and Frontier. With an average price for the route of $627 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 $233 and an overall rating of 6.2.

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

    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 Chicago Midway Airport to Portland.

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

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

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

    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 Portland from Chicago Midway Airport 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 Chicago Midway Airport to Portland?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 3 airlines serving from Midway to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. 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 Midway to Portland? 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
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
7.9Comfort
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’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

they made me check my carryon. There was space in the overhead bins.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

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 Chicago to Portland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Portland found on KAYAK in the last 72 hours.
6/15Sat
1 stopFrontier
12h 19mMDW-PDX
$91
5/29Wed
1 stopFrontier
27h 47mMDW-PDX
$95
5/25Sat
1 stopFrontier
13h 10mMDW-PDX
$96
6/3Mon
3 stops
42h 36mMDW-PDX
$192
6/3Mon
2 stops
24h 57mMDW-PDX
$258
7/21Sun
1 stopDelta
6h 15mMDW-PDX
$313
5/29Wed
1 stopDelta
7h 50mMDW-PDX
$318
6/5Wed
3 stopsWestJet
27h 33mMDW-PDX
$464
10/15Tue
3 stopsWestJet
25h 18mMDW-PDX
$530
6/4Tue
3 stopsVolaris
24h 19mMDW-PDX
$746

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Last minute flights from Midway to Portland

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 Chicago to Portland that are departing in the next 10 days.
5/18Sat
multi-stopFrontier
13h 10mMDW-PDX
5/22Wed
multi-stopFrontier
31h 30mPDX-MDW
$213
5/18Sat
multi-stopFrontier
13h 10mMDW-PDX
5/21Tue
multi-stopFrontier
8h 21mPDX-MDW
$219
5/19Sun
multi-stopFrontier
20h 57mMDW-PDX
5/22Wed
multi-stopFrontier
31h 30mPDX-MDW
$252
5/17Fri
multi-stopFrontier
11h 51mMDW-PDX
5/18Sat
multi-stopFrontier
8h 36mPDX-MDW
$256
5/18Sat
multi-stopFrontier
13h 10mMDW-PDX
5/19Sun
multi-stopFrontier
8h 31mPDX-MDW
$264
5/17Fri
multi-stopFrontier
11h 51mMDW-PDX
5/18Sat
multi-stopFrontier
8h 36mPDX-MDW
$265
5/18Sat
multi-stopDelta
8h 23mMDW-PDX
5/22Wed
multi-stopDelta
7h 08mPDX-MDW
$540
5/17Fri
multi-stopDelta
6h 15mMDW-PDX
5/20Mon
multi-stopDelta
8h 04mPDX-MDW
$907
5/17Fri
multi-stop
28h 11mMDW-PDX
5/21Tue
multi-stop
13h 23mPDX-MDW
$960
5/19Sun
multi-stopDelta
8h 55mMDW-PDX
5/21Tue
multi-stopDelta
6h 07mPDX-MDW
$1,782

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Chicago Midway Airport - Portland Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago Midway Airport

Cabin classes: