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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 9/5. 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
Sat 5/25
Sat 6/1

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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$405
Fairbanks
Fairbanks2 stops$562

Good to know

Low season

April

High season

June

Cheapest flight

$206
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 83% 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 13% 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 10975 reviews
8.6crew
8.2boarding
8.0entertainment
7.9comfort
7.4food
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

I paid just under 200 for flight and luggage, then paid 200 to change the flight, then paid 100 for a carry on. Then the cancelled the flight. Of the 500 I spent they refunded 250. I bought a delta flight for 270 never flew with spirit, but spirit kept 250, not even refunding the 100 for the carry on though they cancelled the flight (for weather on a day with only a slight rain ).

Flight attendants heavily pushed their affinity credit card. Very annoying

They charged me 212.00 for a heavy check in bag at the gate. The pricing and process was so confusing - as if it was designed to purposefully gouge customers who need to board plane. That experience combined with the outrageous price charged will prevent me from ever flying Spirit again. And I’ll be sure to tell the story to anyone who cares to hear.

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Chicago to Alaska

Recent round-trip flight deals

10/5Sat
1 stopDelta
10h 26mMDW-ANC
10/6Sun
1 stopDelta
8h 50mANC-MDW
$405
9/29Sun
1 stopDelta
8h 41mMDW-ANC
10/6Sun
1 stopDelta
8h 50mANC-MDW
$410
9/26Thu
2 stopsDelta
13h 44mMDW-ANC
10/6Sun
1 stopDelta
7h 46mANC-MDW
$415
9/17Tue
1 stopDelta
9h 56mMDW-ANC
9/28Sat
2 stopsDelta
13h 41mANC-MDW
$417
9/18Wed
2 stopsDelta
13h 44mMDW-ANC
10/1Tue
2 stopsDelta
13h 23mANC-MDW
$422
9/16Mon
1 stopDelta
9h 56mMDW-ANC
9/28Sat
1 stopDelta
8h 50mANC-MDW
$432
8/22Thu
1 stopDelta
8h 32mMDW-ANC
8/26Mon
2 stopsDelta
13h 23mANC-MDW
$439
10/15Tue
2 stopsDelta
12h 54mMDW-ANC
10/22Tue
2 stopsDelta
13h 45mANC-MDW
$444
5/25Sat
1 stopDelta
10h 29mMDW-ANC
5/27Mon
1 stopDelta
7h 55mANC-MDW
$457
6/16Sun
1 stopDelta
15h 10mMDW-ANC
6/23Sun
1 stopDelta
15h 09mANC-MDW
$462

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Recent one-way flight deals

9/5Thu
1 stopDelta
10h 17mMDW-ANC
$206
10/4Fri
2 stopsDelta
13h 26mMDW-FAI
$207
9/5Thu
2 stopsDelta
11h 45mMDW-ANC
$211
9/4Wed
2 stopsDelta
17h 17mMDW-ANC
$217
9/3Tue
2 stopsDelta
17h 17mMDW-ANC
$247
7/5Fri
1 stopDelta
8h 24mMDW-ANC
$258
5/25Sat
1 stopDelta
10h 29mMDW-ANC
$291
8/14Wed
2 stopsDelta
13h 42mMDW-ANC
$300
5/25Sat
2 stopsDelta
15h 37mMDW-ANC
$302
9/5Thu
3 stops
41h 28mMDW-ANC
$631

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Last minute flights from Midway to Alaska

Last minute flight, train and bus deals

4/30Tue
multi-stopDelta
11h 12mMDW-ANC
5/8Wed
multi-stopDelta
7h 55mANC-MDW
$649
4/30Tue
multi-stopDelta
10h 38mMDW-ANC
5/8Wed
multi-stopDelta
8h 52mANC-MDW
$654
4/30Tue
multi-stopDelta
10h 38mMDW-ANC
5/8Wed
multi-stopDelta
12h 46mANC-MDW
$661
4/28Sun
multi-stopDelta
15h 34mMDW-ANC
5/3Fri
multi-stopDelta
16h 04mANC-MDW
$925
4/28Sun
multi-stopDelta
15h 34mMDW-ANC
5/3Fri
multi-stopDelta
10h 36mANC-MDW
$994
4/28Sun
multi-stopDelta
11h 12mMDW-ANC
5/3Fri
multi-stopDelta
10h 36mANC-MDW
$1,107
4/30Tue
multi-stopDelta
10h 38mMDW-ANC
5/7Tue
multi-stopDelta
13h 21mANC-MDW
$1,566
4/30Tue
multi-stopDelta
11h 12mMDW-ANC
5/7Tue
multi-stopDelta
13h 21mANC-MDW
$1,733
4/28Sun
multi-stopDelta
17h 19mMDW-ANC
5/2Thu
multi-stopDelta
12h 35mANC-MDW
$2,881

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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: