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Find cheap flights from Chicago Midway Airport to Alaska from $202

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 8/20. 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
Mon 7/1
Mon 7/8

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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$409

Good to know

High season

June

Cheapest flight

$202
Most popular time to fly with an average 43% increase in price.
Flight from Chicago Midway Airport to Fairbanks

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 16% 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 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 10419 reviews
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

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

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

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.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap flights from Chicago to Alaska

Recent round-trip flight deals

7/29Mon
2 stopsDelta
17h 45mMDW-FAI
8/9Fri
1 stopDelta
10h 24mFAI-MDW
$409
7/5Fri
1 stopDelta
8h 24mMDW-ANC
8/16Fri
1 stopDelta
9h 38mANC-MDW
$410
7/29Mon
2 stopsDelta
17h 45mMDW-FAI
8/5Mon
2 stopsDelta
11h 37mFAI-MDW
$414
9/20Fri
2 stopsDelta
12h 54mMDW-ANC
9/27Fri
1 stopDelta
8h 50mANC-MDW
$415
8/12Mon
1 stopDelta
8h 23mMDW-ANC
8/19Mon
2 stopsDelta
9h 42mANC-MDW
$417
9/28Sat
2 stopsDelta
11h 32mMDW-ANC
10/2Wed
2 stopsDelta
13h 41mANC-MDW
$422
7/5Fri
1 stopDelta
8h 24mMDW-ANC
8/24Sat
1 stopDelta
9h 38mANC-MDW
$432
8/14Wed
1 stopDelta
9h 30mMDW-FAI
8/20Tue
1 stopDelta
7h 37mFAI-MDW
$433
7/4Thu
3 stops
42h 36mMDW-ANC
7/7Sun
2 stops
27h 01mANC-MDW
$662
7/4Thu
3 stops
42h 36mMDW-ANC
7/7Sun
3 stops
27h 01mANC-MDW
$712

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Recent one-way flight deals

8/20Tue
1 stopDelta
9h 30mMDW-FAI
$202
9/24Tue
1 stopDelta
8h 41mMDW-ANC
$206
8/5Mon
2 stopsDelta
13h 26mMDW-FAI
$207
8/14Wed
2 stopsDelta
13h 49mMDW-ANC
$211
6/30Sun
1 stopDelta
15h 17mMDW-ANC
$228
8/5Mon
1 stopDelta
9h 30mMDW-FAI
$231
8/16Fri
2 stopsDelta
14h 08mMDW-ANC
$233
7/7Sun
1 stopDelta
15h 08mMDW-ANC
$246
9/5Thu
2 stopsDelta
14h 04mMDW-ANC
$251
7/19Fri
3 stops
25h 47mMDW-ANC
$421

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Last minute flights from Midway to Alaska

Last minute flight, train and bus deals

6/2Sun
multi-stopDelta
8h 19mMDW-ANC
6/8Sat
multi-stopDelta
9h 30mANC-MDW
$598
6/2Sun
multi-stopDelta
8h 19mMDW-ANC
6/8Sat
multi-stopDelta
12h 39mANC-MDW
$605
6/2Sun
multi-stopDelta
8h 19mMDW-ANC
6/7Fri
multi-stopDelta
14h 10mANC-MDW
$630
6/3Mon
multi-stopDelta
8h 19mMDW-ANC
6/5Wed
multi-stopDelta
7h 55mANC-MDW
$658
6/3Mon
multi-stopDelta
8h 19mMDW-ANC
6/4Tue
multi-stopDelta
13h 21mANC-MDW
$665
6/3Mon
multi-stopDelta
14h 01mMDW-ANC
6/10Mon
multi-stopDelta
12h 39mANC-MDW
$706
6/4Tue
multi-stopDelta
9h 27mMDW-ANC
6/8Sat
multi-stopDelta
14h 16mANC-MDW
$761
6/5Wed
multi-stopDelta
17h 44mMDW-FAI
6/12Wed
multi-stopDelta
7h 56mFAI-MDW
$768
6/5Wed
multi-stopDelta
17h 44mMDW-FAI
6/11Tue
multi-stopDelta
13h 46mFAI-MDW
$773
6/3Mon
multi-stopDelta
14h 01mMDW-ANC
6/5Wed
multi-stopDelta
7h 55mANC-MDW
$844

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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: