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Find cheap flights from Chicago Midway Airport to Oregon from $94

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 6/10. 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 6/21
Fri 6/28

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Best Oregon Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Portland
Portland1 stop$180
Eugene
Eugene2 stops$343
Redmond
Redmond2 stops$388
Medford
Medford2 stops$471
Boise
Boise2 stops$273

Good to know

Low season

January

High season

July

Cheapest flight

$94
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

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 to Oregon 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 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 to Oregon with an airline and back to Chicago Midway Airport 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 to Oregon 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

Top tips for finding cheap flights to Oregon

  • Morning departure is around 23% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Oregon

 
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
DeltaOverall score based on 10585 reviews
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
7.9Comfort
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

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!!!!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

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.

Book cheap flights from Chicago to Oregon

Recent round-trip flight deals

5/28Tue
1 stopFrontier
12h 38mMDW-PDX
5/29Wed
1 stopFrontier
8h 36mPDX-MDW
$180
6/1Sat
1 stopFrontier
20h 38mMDW-PDX
6/4Tue
1 stopFrontier
9h 11mPDX-MDW
$183
5/31Fri
1 stopFrontier
24h 52mMDW-PDX
6/2Sun
1 stopFrontier
8h 21mPDX-MDW
$184
6/5Wed
1 stopFrontier
9h 32mMDW-PDX
6/8Sat
2 stopsFrontier
9h 19mPDX-MDW
$185
5/28Tue
1 stopFrontier
12h 38mMDW-PDX
6/7Fri
1 stopFrontier
10h 39mPDX-MDW
$187
5/28Tue
1 stopFrontier
12h 38mMDW-PDX
6/3Mon
1 stopFrontier
11h 14mPDX-MDW
$188
7/10Wed
2 stopsDelta
11h 51mMDW-BOI
7/15Mon
1 stopDelta
7h 03mBOI-MDW
$273
6/4Tue
1 stopDelta
5h 40mMDW-BOI
6/8Sat
2 stopsDelta
10h 34mBOI-MDW
$293
7/10Wed
1 stopDelta
5h 50mMDW-BOI
7/15Mon
1 stopDelta
7h 03mBOI-MDW
$303
6/14Fri
3 stops
33h 20mMDW-BOI
6/17Mon
3 stops
22h 17mBOI-MDW
$726

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Recent one-way flight deals

6/10Mon
1 stopFrontier
20h 57mMDW-PDX
$94
6/2Sun
1 stopFrontier
10h 26mMDW-PDX
$95
6/1Sat
1 stopFrontier
13h 10mMDW-PDX
$96
6/3Mon
1 stopFrontier
17h 15mMDW-PDX
$99
5/28Tue
1 stopFrontier
12h 38mMDW-PDX
$100
7/27Sat
1 stopDelta
5h 45mMDW-BOI
$124
7/12Fri
1 stopDelta
5h 54mMDW-BOI
$144
6/13Thu
3 stops
29h 11mMDW-PDX
$264
6/28Fri
3 stops
26h 25mMDW-PDX
$335
6/29Sat
3 stopsWestJet
26h 21mMDW-PDX
$525

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Last minute flights from Midway to Oregon

Last minute flight, train and bus deals

5/25Sat
multi-stopFrontier
13h 10mMDW-PDX
5/31Fri
multi-stopFrontier
11h 42mPDX-MDW
$180
5/26Sun
multi-stopFrontier
12h 28mMDW-PDX
5/28Tue
multi-stopFrontier
25h 02mPDX-MDW
$203
5/25Sat
multi-stopFrontier
13h 10mMDW-PDX
5/28Tue
multi-stopFrontier
8h 21mPDX-MDW
$219
5/25Sat
multi-stopFrontier
13h 10mMDW-PDX
5/28Tue
multi-stopFrontier
7h 05mPDX-MDW
$223
5/25Sat
multi-stopFrontier
13h 10mMDW-PDX
5/31Fri
multi-stopFrontier
11h 42mPDX-MDW
$259
5/25Sat
multi-stopDelta
8h 25mMDW-PDX
5/29Wed
multi-stopDelta
7h 50mPDX-MDW
$480
5/24Fri
multi-stopDelta
6h 13mMDW-PDX
6/1Sat
multi-stopDelta
8h 40mPDX-MDW
$565
5/27Mon
multi-stop
29h 43mMDW-PDX
6/6Thu
multi-stop
23h 49mPDX-MDW
$1,190
5/23Thu
multi-stopWestJet
29h 24mMDW-PDX
5/26Sun
multi-stopWestJet
31h 52mPDX-MDW
$1,352
5/23Thu
multi-stop
25h 18mMDW-BOI
5/25Sat
multi-stop
23h 01mBOI-MDW
$2,108

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Chicago Midway Airport - Oregon Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Oregon - Chicago Midway Airport

Cabin classes: