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Find cheap flights from Chicago Midway Airport to Alaska from $206

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 Alaska departing on 8/10. 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
sáb 6/22
sáb 6/29

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Best Alaska Flight Deals

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

Anchorage
Anchorage1 stop$410
Fairbanks
Fairbanks2 stops$414

Good to know

High season

June

Cheapest flight

$206
Most popular time to fly with an average 43% increase in price.
Flight from Chicago Midway Airport to Anchorage

FAQs - booking Alaska flights

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

    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 Alaska.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Alaska 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 Alaska?

    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 Alaska 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 Alaska?

    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 Alaska 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 Alaska

  • Morning departure is around 12% cheaper 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 Alaska

 
Need help choosing which airline to fly with from Midway to Alaska? 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 10561 reviews
8.0Entertainment
7.9Comfort
8.6Crew
7.4Food
8.2Boarding
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 Alaska

Recent round-trip flight deals

6/22sáb
1 stopDelta
12h 20mMDW-ANC
6/24seg
1 stopDelta
8h 29mANC-MDW
$410
9/25qua
2 stopsDelta
14h 16mMDW-FAI
10/1ter
2 stopsDelta
14h 10mFAI-MDW
$414
9/20sex
2 stopsDelta
12h 54mMDW-ANC
9/27sex
1 stopDelta
8h 50mANC-MDW
$415
9/28sáb
1 stopDelta
10h 26mMDW-ANC
10/1ter
2 stopsDelta
13h 23mANC-MDW
$417
9/28sáb
2 stopsDelta
13h 45mMDW-ANC
10/2qua
2 stopsDelta
13h 41mANC-MDW
$422
6/22sáb
1 stopDelta
12h 20mMDW-ANC
6/28sex
1 stopDelta
14h 19mANC-MDW
$432
10/28seg
2 stopsDelta
13h 56mMDW-ANC
11/15sex
1 stopDelta
9h 27mANC-MDW
$437
6/25ter
2 stopsDelta
17h 46mMDW-FAI
7/1seg
1 stopDelta
10h 30mFAI-MDW
$437
8/12seg
1 stopDelta
8h 32mMDW-ANC
8/19seg
2 stopsDelta
13h 37mANC-MDW
$439
6/17seg
3 stops
26h 16mMDW-ANC
6/24seg
3 stops
29h 21mANC-MDW
$971

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Recent one-way flight deals

8/10sáb
1 stopDelta
12h 15mMDW-ANC
$206
9/5qui
2 stopsDelta
13h 34mMDW-ANC
$211
7/2ter
1 stopDelta
12h 18mMDW-ANC
$228
8/14qua
2 stopsDelta
13h 56mMDW-ANC
$233
8/6ter
2 stopsDelta
15h 58mMDW-ANC
$239
7/1seg
1 stopDelta
12h 18mMDW-ANC
$251
8/5seg
1 stopDelta
9h 53mMDW-FAI
$261
6/3seg
1 stopDelta
8h 19mMDW-ANC
$270
8/6ter
2 stopsDelta
17h 43mMDW-FAI
$272
8/14qua
3 stops
42h 37mMDW-ANC
$546

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Last minute flights from Midway to Alaska

Last minute flight, train and bus deals

5/24sex
multi-stopDelta
8h 19mMDW-ANC
6/8sáb
multi-stopDelta
9h 30mANC-MDW
$598
5/26dom
multi-stopDelta
13h 10mMDW-ANC
6/2dom
multi-stopDelta
8h 52mANC-MDW
$603
5/24sex
multi-stopDelta
8h 19mMDW-ANC
6/8sáb
multi-stopDelta
12h 33mANC-MDW
$605
5/24sex
multi-stopDelta
9h 27mMDW-ANC
5/26dom
multi-stopDelta
7h 55mANC-MDW
$658
5/25sáb
multi-stopDelta
11h 04mMDW-ANC
5/27seg
multi-stopDelta
8h 52mANC-MDW
$663
5/24sex
multi-stopDelta
9h 27mMDW-ANC
5/26dom
multi-stopDelta
15h 27mANC-MDW
$665
5/28ter
multi-stopDelta
8h 19mMDW-ANC
6/1sáb
multi-stopDelta
12h 46mANC-MDW
$746
5/28ter
multi-stopDelta
13h 36mMDW-ANC
5/31sex
multi-stopDelta
12h 09mANC-MDW
$811
5/25sáb
multi-stopDelta
13h 06mMDW-ANC
5/27seg
multi-stopDelta
14h 36mANC-MDW
$961
5/28ter
multi-stopDelta
13h 36mMDW-ANC
6/1sáb
multi-stopDelta
11h 48mANC-MDW
$1,302

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Chicago Midway Airport - Alaska Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Alaska - Chicago Midway Airport

Cabin classes: