$90 Find Cheap Flights from Chicago Midway Airport to Oregon

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 Oregon departing on 8/31. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon, 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 Oregon, as well as popular online travel agencies
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Flights Deals

Best Oregon Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$181
Eugene
Eugene1 stop$333
Redmond
Redmond2 stops$289
Medford
Medford2 stops$718
Boise
Boise1 stop$195
Portland
Portlandnonstop$181
Eugene
Eugene1 stop$333
Redmond
Redmond2 stops$289
Medford
Medford2 stops$718
Boise
Boise1 stop$195

Cheap Flights from Midway to Oregon

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Oregon 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Oregon

Wed, Sep 10 - Sat, Sep 13
Southwest Logo
8:30 am - 10:50 amMDW-PDX
4h 20mnonstop
Southwest Logo
6:00 am - 12:00 pmPDX-MDW
4h 00mnonstop
$181Southwest
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Tue, Sep 16 - Sat, Sep 20
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
11:00 am - 7:05 pmPDX-MDW
6h 05m1 stop
$191Southwest
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Wed, Aug 27 - Fri, Aug 29
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
1:35 pm - 7:35 pmPDX-MDW
4h 00mnonstop
$194Southwest
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Wed, Aug 20 - Wed, Oct 22
Delta Logo
9:15 am - 2:01 pmMDW-BOI
5h 46m1 stop
Delta Logo
1:43 pm - 9:44 pmBOI-MDW
7h 01m1 stop
$195Delta
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Wed, Sep 10 - Sat, Sep 13
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
4:00 pm - 5:10 amPDX-MDW
11h 10m1 stop
$196Southwest
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Sat, Aug 16 - Tue, Aug 19
Delta Logo
7:17 pm - 11:54 pmMDW-BOI
5h 37m1 stop
Delta Logo
8:40 am - 5:37 pmBOI-MDW
7h 57m2 stops
$200Delta
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Wed, Sep 24 - Tue, Sep 30
Delta Logo
9:20 am - 4:07 pmMDW-PDX
8h 47m1 stop
Delta Logo
6:04 am - 4:23 pmPDX-MDW
8h 19m1 stop
$201Delta
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Thu, Oct 9 - Mon, Oct 13
Frontier Logo
4:29 pm - 7:57 amMDW-PDX
17h 28m1 stop
Frontier Logo
8:57 am - 10:38 pmPDX-MDW
11h 41m1 stop
$248Frontier
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Thu, Sep 11 - Sun, Sep 14
Frontier Logo
4:29 pm - 12:16 amMDW-PDX
9h 47m1 stop
Frontier Logo
6:05 am - 7:01 pmPDX-MDW
10h 56m1 stop
$288Frontier
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Fri, Aug 29 - Mon, Sep 1
Frontier Logo
6:31 pm - 12:15 amMDW-PDX
7h 44m1 stop
Frontier Logo
12:18 pm - 12:24 amPDX-MDW
10h 06m1 stop
$321Frontier
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Useful Info

KAYAK's insights & trends for Midway to Oregon flights

Get data-powered insights and trends into flights from Midway to Oregon to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Oregon flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Oregon.

The cheapest ticket to Oregon from Chicago Midway Airport found in the last 72 hours was to Portland, at $234 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $234.

Can I save money by flying with a layover from Chicago Midway Airport to Oregon?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $328, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Oregon, 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 Oregon is January, when tickets cost $266 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $593 and $555 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Oregon?

The average price of all round-trip flights from Chicago Midway Airport to Oregon clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Oregon on a Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.


Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$90
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to Portland

FAQs - booking Oregon flights

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

    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 Oregon.

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

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

    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 from Chicago Midway Airport to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Oregon?

    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 from Chicago Midway Airport to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Oregon?

    The cheapest time of day to fly to Oregon is generally in the morning, when round-trip flights cost $328 on average. Morning departures are around 22% cheaper than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the evening, which is peak travel time and where the average cost of a ticket is $419.

Top airlines flying from Midway to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oregon. 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 Oregon? 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
SouthwestOverall score based on 4287 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

Everything you need to know for your flight from Midway to Oregon

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