Find cheap flights from Chicago Midway Airport to Alaska

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MDW — Alaska
Dec 26 — Jan 21
Round-trip
1 adult
Economy
0 bags
From?
To?
Mon 12/26
Mon 1/2

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Latest Alaska Flight Deals

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

MOST POPULARAnchorage
1 stop from $338
Fairbanks
2+ stops from $821

Good to know

Low season

January

High season

May

Cheapest flight

$174

Good deal one-way

$584
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway to Anchorage
or less

Top tips for finding cheap flights to Alaska

  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be June and July. The cheapest month to fly to Alaska is January.
  • Morning departure is around 60% 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

FAQs - booking Alaska flights

Top airline flying Chicago Midway to Alaska

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31824 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Gate agents in Seattle were fabulous and extra observant. Thanks for doing a great job!

Read more about Delta

Gate agents in Seattle were fabulous and extra observant. Thanks for doing a great job!

It was really full but that’s how it goes.

Pros: "Clean safe comfortable plane seats. friendly staff."
Cons: "A small credit for miles as the Wifi didn’t work."
Pros: "Crew was friendly and very clear about masks."
Cons: "My sister’s checked in luggage was in poor shape when we got it in Albany. We noticed an outside compartment was unzipped. So we checked to see if anything was missing and a souvenir from Mexico was gone. Then we realized a zipper was missing from the luggage and then decided to check all the other compartments and realized her bag of jewelry was gone. The woman at baggage services in Albany told us Delta is not responsible for lost belongings. Also tried to tell us theft is not an issue because there are cameras everywhere. Well you are telling someone that is missing a bag of jewelry that theft is not a problem. Also, there may be cameras everywhere but I doubt anyone is going to review those cameras to see what happened. I will never fly Delta again."
Pros: "Crew nailed it. Came by not just for food and drinks but also frequently enough to collect trash/plates/empty cups."
Pros: "Entertainment selection was nice."
Cons: "Seats were too tightly packed in. Person in front reclined their seat and I couldn't even reach my bag under the seat. Very uncomfortable. And I'm small/short."
Pros: "Handing by any cap was great to get us on the plane on time."
Cons: "The plane we got on time to board was delayed enough to miss our connecting flight, so delayed another 3 hours when missing the next flight."
Pros: "Crew is amazing, seats are pretty good."
Cons: "On time, baggages checked in and were made available on time."
Pros: "Standard boarding The plane was on time"
Cons: "Better boarding process.Such as the one used by Southwest"
Pros: "Use my built up miles for the SEA-ANC leg of our trip, as to physically price it out as one ticket usually increases the fare by 300-600 u$d depending upon time of year. As it was the tail end of an already long journey (OKA-ICN/ICN-SEA), booked the First Class Cabin. Every mile was worth it."
Cons: "N/A"
Cons: "Food really bad on both segments."
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Cons: "Air conditioning was very loud"
Pros: "The turkey sandwich was okay."
Cons: "I was seated next to an extremely large man. I possessed only half of my seat for the duration of the six hour flight. I asked a flight attendant to move me but she said the flight was full. There should be a protocol for passengers over 300 lbs."
Pros: "The entertainment was nice."
Cons: "If the screen wasn’t behind the seat. I could hear the tapping of the person behind me."
Cons: "Being on time"
Pros: "Crew were caring and friendly... seemed sincere"
Cons: "My husband and I had reserved seats next to each other but then today they had been rearranged and we couldn’t sit together which was annoying and disappointing especially as this was a treat to just come to Charleston together ... this seems wrong when we have paid for tickets together"
Pros: "Very friendly crew with a clean plane!"
Cons: "N/A"
Cons: "At least one hour late"
Pros: "I liked that military boarded first."
Cons: "I think disabled US Veterans should board with active duty and retired military"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Pros: "Nothing"
Cons: "Everything. Stinky, dirty cabin. No running water in the bathrooms. Delays on the tarmac."
Pros: "Super friendly flight crew."
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "Everyone very friendly and courteous."
Cons: "Snacks are very small quantity and often stale"
Pros: "Everything was perfect, everyone was nice, there was lots of room, the crew offered snacks frequently, WiFi had a great connection and there was a wide array of entertainment."
Cons: "There was a problem with the plane that they told us after we boarded that delayed our plane an hour. But hey, better safe than sorry!"
Pros: "Seating"
Cons: "The re route to MSP... Seven hour flight time for a two and half hour flight..."
Pros: "Very good flight. Nice staff that seemed to enjoy their jobs. Great smiles and personable. Modern and clean plane with WiFi and charging outlets"
Cons: "There was a mechanical issue that delayed departure. Fortunately I did not have a connection to make. The crew made sure to communicate with everyone onboard frequently so we were aware of the situation and progress. They handled everything well which was reassuring for my peace of mind."
Pros: "The crew was amazingly helpful!"
Pros: "Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!"
Cons: "Nothing."
Pros: "I LOVED the free movies. Great idea and newer movies. Finally was able to watch a movie I'd wanted to see for a long time."
Cons: "Flight was packed which always makes for a more cramped ride. Again, boarding. Flight boarded late and just seems boarding from the back to front would be faster."
Pros: "The staff and crew were great help all along the route and the planes were well kept and clean."
Cons: "One of the legs did not have the free wifi available, but they mentioned that before takeoff and were very apologetic that it had not been added to that plane yet."
Cons: "When they called for passengers with infants and those who needed more time they also called for anyone who wanted to check their luggage. So of course people cut right in front of me as I was about to scan my pass. What is the point of asking us to come up if they are just going to let people jump in front of me."
Cons: "The air conditioning was broken so it was sweltering the whole time. Staff didn't even mention it or apologize. No leg room. Bags took longer than 20 minutes to arrive but we didn't make a fuss since we were just glad to be finished with Delta. I'll never fly Delta again even if it costs me more."
Pros: "Fast flight"
Cons: "Long wait in hot plane before take off."
Pros: "Food was nice and plenty. Great movie selection. Very polite crew."
Cons: "The seat was a bit uncomfortable and not big enough."
Cons: "Didn't stick to zones when boarding customers. Gate agent basically let anyone board during pre boarding and priority boarding, why even offer it if you aren't going to make people adhere to the rules."
Pros: "Friendly staff/ comfortable seating."
Pros: "Turbulence didn't allow the beverage cart to serve passengers"
Pros: "The crew was great on both Korean air and Delta. Very helpful and polite, with several going the extra mile"
Cons: "I'm tall, so I'd like bigger seats, but I guess that can't be helped much without a price increase"
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Good entertainment with games for kids, movies etc."
Cons: "No meals (5+ of flying), need to buy earphones, no place for hand lauggudge"
Pros: "I felt the entire flight crew was there to make my trip more pleasant. The plane was new and had free video and usb outlets to charge my devices."
Cons: "Nothing, truly an excellent experience."
Pros: "Low price."
Cons: "Delta provided no information as to why the flight was late. No earlier flights on other airlines were offered."
Pros: "Seated my husband I together (finally) at very back of plane next to window (not our preference)."
Cons: "My husband and I although booked together were seated in middle seats 9 rows apart. We atrempted to change our seats online at KLM (not possible), online at Delta (didn't recognize our KLM purchased flight), in person at KLM counter in SVG, in person with THE Delta rep at the check-in gate in AMS...no one could help us due to different systems used for seating for each company that the other one doesn't have access to. Flights booked by one company and operated by another seem common enough that this system needs to be improved. - Silver KLM travelers Also WAY too hot on plane."
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Cons: "Enforce your baggage size and number limits. A significant number of passengers take bags onboard that are oversized."
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Book cheap flights from Chicago Midway Airport to Alaska

Recent round-trip flight deals

1/20Fri
1 stopDelta
9h 06mMDW-ANC
1/23Mon
1 stopDelta
8h 00mANC-MDW
$338
2/4Sat
2 stopsDelta
14h 46mMDW-ANC
2/10Fri
1 stopDelta
10h 35mANC-MDW
$342
1/20Fri
1 stopDelta
9h 06mMDW-ANC
1/23Mon
2 stopsDelta
14h 55mANC-MDW
$344
2/7Tue
2 stopsDelta
11h 53mMDW-ANC
2/10Fri
2 stopsDelta
12h 28mANC-MDW
$348
1/19Thu
1 stopDelta
9h 06mMDW-ANC
1/23Mon
1 stopDelta
8h 00mANC-MDW
$367
1/18Wed
2 stopsDelta
12h 22mMDW-ANC
1/22Sun
1 stopDelta
8h 00mANC-MDW
$371
1/19Thu
1 stopDelta
9h 06mMDW-ANC
1/23Mon
2 stopsDelta
14h 55mANC-MDW
$373
1/18Wed
2 stopsDelta
12h 22mMDW-ANC
1/22Sun
2 stopsDelta
14h 30mANC-MDW
$377
2/5Sun
1 stopDelta
11h 25mMDW-ANC
2/9Thu
2 stopsDelta
14h 28mANC-MDW
$383
2/7Tue
2 stopsDelta
11h 53mMDW-ANC
2/11Sat
2 stopsDelta
14h 40mANC-MDW
$400
1/20Fri
1 stopDelta
9h 06mMDW-ANC
1/24Tue
2 stopsDelta
15h 24mANC-MDW
$406
2/6Mon
2 stopsDelta
15h 58mMDW-ANC
2/10Fri
2 stopsDelta
14h 28mANC-MDW
$410
1/20Fri
1 stopDelta
9h 06mMDW-ANC
1/22Sun
2 stopsDelta
15h 01mANC-MDW
$436
2/17Fri
2 stopsDelta
14h 25mMDW-ANC
2/24Fri
2 stopsDelta
13h 53mANC-MDW
$437
2/6Mon
2 stopsDelta
15h 58mMDW-ANC
2/9Thu
2 stopsDelta
13h 25mANC-MDW
$439
1/20Fri
1 stopDelta
9h 06mMDW-ANC
1/23Mon
2 stopsDelta
15h 01mANC-MDW
$456
2/17Fri
1 stopDelta
9h 57mMDW-ANC
2/23Thu
2 stopsDelta
14h 20mANC-MDW
$463
1/13Fri
1 stopDelta
14h 14mMDW-ANC
1/20Fri
1 stopDelta
10h 33mANC-MDW
$476
12/16Fri
2 stopsMultiple Airlines
18h 49mMDW-ANC
12/18Sun
1 stopMultiple Airlines
13h 36mANC-MDW
$584
2/7Tue
2 stopsMultiple Airlines
15h 11mMDW-ANC
2/12Sun
1 stopMultiple Airlines
13h 35mANC-MDW
$593

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Recent one-way flight deals

12/14Wed
2 stopsDelta
13h 27mMDW-ANC
$174
12/13Tue
2 stopsMultiple Airlines
37h 24mMDW-ANC
$184
12/15Thu
1 stopDelta
10h 07mMDW-ANC
$199
1/31Tue
2 stopsDelta
12h 22mMDW-ANC
$203
12/16Fri
2 stopsMultiple Airlines
31h 18mMDW-ANC
$212
12/16Fri
2 stopsMultiple Airlines
31h 18mMDW-ANC
$218
12/15Thu
2 stopsMultiple Airlines
31h 44mMDW-ANC
$220
12/17Sat
2 stopsMultiple Airlines
30h 49mMDW-ANC
$226
12/18Sun
2 stopsMultiple Airlines
31h 06mMDW-ANC
$245
12/12Mon
2 stopsMultiple Airlines
22h 45mMDW-ANC
$253
12/14Wed
1 stopMultiple Airlines
26h 25mMDW-ANC
$254
12/5Mon
1 stopDelta
10h 07mMDW-ANC
$259
12/2Fri
2 stopsDelta
13h 27mMDW-ANC
$263
12/21Wed
2 stopsMultiple Airlines
25h 04mMDW-FAI
$318
12/2Fri
1 stopDelta
10h 07mMDW-ANC
$319
12/21Wed
3 stopsMultiple Airlines
39h 15mMDW-FAI
$321
5/17Wed
2 stopsMultiple Airlines
37h 45mMDW-ANC
$324
12/3Sat
2 stopsDelta
13h 50mMDW-ANC
$413
12/16Fri
1 stopDelta
10h 07mMDW-ANC
$419
12/1Thu
1 stopDelta
10h 07mMDW-ANC
$429

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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:

$556
$1,283

Browse destinations: