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$90 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 6/12. 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 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 43,369,418 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Portland 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
7:35 am - 4:42 pmMDW-PDX
11h 07m1 stop
12:43 am - 1:49 pmPDX-MDW
11h 06m1 stop
$179Frontier
Find Deal
Thu, May 16 - Mon, May 20
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
12:49 am - 12:00 pmPDX-MDW
9h 11m1 stop
$180Frontier
Find Deal
Sat, Jun 8 - Tue, Jun 11
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
12:48 am - 11:13 amPDX-MDW
8h 25m1 stop
$181Frontier
Find Deal
Sat, May 25 - Fri, May 31
5:30 am - 11:59 pmMDW-PDX
20h 29m1 stop
12:48 am - 9:06 pmPDX-MDW
18h 18m1 stop
$183Frontier
Find Deal
Tue, May 14 - Fri, May 17
9:05 pm - 10:04 pmMDW-PDX
26h 59m1 stop
4:00 pm - 5:50 amPDX-MDW
11h 50m2 stops
$184Frontier
Find Deal
Sat, May 25 - Sat, Jun 1
5:01 am - 6:48 amMDW-PDX
27h 47m1 stop
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$185Frontier
Find Deal
Wed, May 22 - Tue, May 28
10:59 pm - 9:15 amMDW-PDX
12h 16m1 stop
4:00 pm - 5:50 amPDX-MDW
11h 50m2 stops
$186Frontier
Find Deal
Sat, May 11 - Sat, May 18
10:59 pm - 9:15 amMDW-PDX
12h 16m1 stop
4:00 pm - 5:50 amPDX-MDW
11h 50m2 stops
$187Frontier
Find Deal
Sat, May 11 - Sat, May 18
5:00 pm - 11:25 pmMDW-PDX
8h 25m1 stop
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
$232Delta
Find Deal
Sat, May 25 - Thu, May 30
5:00 pm - 11:25 pmMDW-PDX
8h 25m1 stop
6:15 am - 4:55 pmPDX-MDW
8h 40m1 stop
$248Delta
Find Deal
Sat, May 25 - Sat, Jun 1

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 $426 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 52 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Portland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Portland from Chicago Midway Airport were found on Frontier ($90) and Delta ($151), and the lowest round-trip tickets were found on Frontier ($179) and Delta ($232).

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

Each day, there are between 1 and 4 nonstop flights that take off from Chicago Midway Airport and land in Portland, with an average flight time of 4h 21m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 14 flights. The most frequent day of departure is Wednesday, when 29% of all weekly flights depart. The fewest flights depart on a Thursday.

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

Direct flights take on average 4h 20m to travel the 1,746 miles between Chicago Midway Airport and Portland.

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

$90
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 19% 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 $90 for a one-way ticket and $179 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 $615 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 $221 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 10838 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

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

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

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

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

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.

Plane was so old it had cigarette butt trays in the seat

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 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.
6/12Wed
1 stopFrontier
9h 32mMDW-PDX
$90
5/11Sat
1 stopFrontier
12h 16mMDW-PDX
$91
5/16Thu
1 stopFrontier
27h 21mMDW-PDX
$95
5/28Tue
1 stopFrontier
12h 38mMDW-PDX
$96
5/17Fri
1 stopFrontier
20h 42mMDW-PDX
$99
5/17Fri
1 stopFrontier
20h 42mMDW-PDX
$100
5/13Mon
1 stopDelta
6h 15mMDW-PDX
$151
5/17Fri
3 stops
39h 03mMDW-PDX
$173
6/17Mon
2 stopsDelta
9h 22mMDW-PDX
$306
6/15Sat
2 stopsDelta
10h 01mMDW-PDX
$427

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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.
5/9Thu
multi-stopFrontier
14h 13mMDW-PDX
5/14Tue
multi-stopFrontier
13h 17mPDX-MDW
$244
5/8Wed
multi-stopFrontier
12h 11mMDW-PDX
5/12Sun
multi-stopFrontier
18h 48mPDX-MDW
$249
5/9Thu
multi-stopFrontier
14h 13mMDW-PDX
5/14Tue
multi-stopFrontier
13h 17mPDX-MDW
$253
5/9Thu
multi-stopFrontier
15h 27mMDW-PDX
5/14Tue
multi-stopFrontier
13h 17mPDX-MDW
$299
5/7Tue
multi-stopFrontier
9h 14mMDW-PDX
5/7Tue
multi-stopFrontier
8h 39mPDX-MDW
$318
5/6Mon
multi-stopFrontier
20h 29mMDW-PDX
5/7Tue
multi-stopFrontier
13h 17mPDX-MDW
$327
5/8Wed
multi-stopFrontier
12h 11mMDW-PDX
5/11Sat
multi-stopFrontier
18h 38mPDX-MDW
$403
5/8Wed
multi-stopFrontier
12h 11mMDW-PDX
5/11Sat
multi-stopFrontier
18h 38mPDX-MDW
$407
5/7Tue
multi-stopDelta
10h 55mMDW-PDX
5/8Wed
multi-stopDelta
7h 08mPDX-MDW
$629
5/6Mon
multi-stopDelta
8h 30mMDW-PDX
5/6Mon
multi-stopDelta
6h 07mPDX-MDW
$764

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Chicago Midway Airport - Portland Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago Midway Airport

Cabin classes: