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Cheap flights from Midway (MDW) to Alaska from $178

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. 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.
MDW — ANC
May 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Alaska?

Travelers have found it’s best to book a flight 42 days in advance to save up to 27% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 42 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Alaska 1-2 weeks in advance for as low as $322, or $606 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to Alaska?

The best pricing can be found in the month of October. Prices to Alaska from Chicago Midway Airport average $472. You can even find prices in October for less than $472, as users have found deals to Alaska from as low as $196. The month of June appears to be one of the more expensive times to travel to Alaska from Chicago Midway Airport. Flying in the targeted month can save you up to 33%.

When is the cheapest time to fly from Chicago Midway Airport to Alaska (MDW - AK)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Alaska as you normally would.

Cheap Delta flights from Midway to Alaska

Explore cheap flight options specifically provided by Delta for the route between Midway and Alaska. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Thu 5/307:10 pmMDW - ANC
1 stop8h 19mDelta
Sun 6/3010:55 pmANC - MDW
1 stop15h 10mDelta
Deal found 5/8$382
Tue 5/281:21 pmMDW - ANC
2 stops10h 21mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$387
Wed 5/292:15 pmMDW - ANC
1 stop9h 27mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$410
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Sun 6/1610:55 pmANC - MDW
1 stop15h 09mDelta
Deal found 5/7$415
Sat 9/285:00 pmMDW - ANC
1 stop10h 26mDelta
Tue 10/112:40 amANC - MDW
2 stops13h 23mDelta
Deal found 5/7$417
Sat 6/85:45 pmMDW - ANC
2 stops22h 25mDelta
Sun 6/165:15 pmANC - MDW
2 stops12h 39mDelta
Deal found 5/7$422
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Thu 6/131:20 amANC - MDW
2 stops28h 28mDelta
Deal found 5/7$426
Fri 6/71:24 pmMDW - ANC
1 stop12h 08mDelta
Fri 6/1411:45 pmANC - MDW
1 stop14h 19mDelta
Deal found 5/8$432
Fri 6/79:34 amMDW - ANC
2 stops27h 06mDelta
Sat 6/158:00 pmANC - MDW
1 stop18h 04mDelta
Deal found 5/7$437

Cheap Midway to Alaska flights in May & June 2024

Find cheap flight options from Midway to Alaska specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,338 searches. Prices were last updated on May 8, 2024.
Thu 5/307:10 pmMDW - ANC
1 stop8h 19mDelta
Sun 6/3010:55 pmANC - MDW
1 stop15h 10mDelta
Deal found 5/8$382
Tue 5/281:21 pmMDW - ANC
2 stops10h 21mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$387
Wed 5/292:15 pmMDW - ANC
1 stop9h 27mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$410
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Sat 6/158:00 pmANC - MDW
1 stop18h 04mDelta
Deal found 5/7$415
Sat 6/85:45 pmMDW - ANC
2 stops22h 25mDelta
Sat 6/158:00 amANC - MDW
2 stops21h 48mDelta
Deal found 5/7$422
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Thu 6/131:20 amANC - MDW
2 stops28h 28mDelta
Deal found 5/7$426
Fri 6/71:24 pmMDW - ANC
1 stop12h 08mDelta
Fri 6/1411:45 pmANC - MDW
1 stop14h 19mDelta
Deal found 5/8$432
Fri 6/79:34 amMDW - ANC
2 stops27h 06mDelta
Sat 6/158:00 pmANC - MDW
1 stop18h 04mDelta
Deal found 5/7$437
Fri 6/71:24 pmMDW - ANC
1 stop12h 08mDelta
Fri 6/145:15 pmANC - MDW
2 stops12h 33mDelta
Deal found 5/8$439

Midway to Alaska 2024 flight deals

Discover exclusive flight deals for travel between Midway and Alaska in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Thu 5/307:10 pmMDW - ANC
1 stop8h 19mDelta
Sun 6/3010:55 pmANC - MDW
1 stop15h 10mDelta
Deal found 5/8$382
Tue 5/281:21 pmMDW - ANC
2 stops10h 21mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$387
Wed 5/292:15 pmMDW - ANC
1 stop9h 27mDelta
Sun 6/29:52 pmANC - MDW
1 stop7h 55mDelta
Deal found 5/7$410
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Sat 6/158:00 pmANC - MDW
1 stop18h 04mDelta
Deal found 5/7$415
Sat 9/285:00 pmMDW - ANC
1 stop10h 26mDelta
Tue 10/112:40 amANC - MDW
2 stops13h 23mDelta
Deal found 5/8$417
Sat 6/85:45 pmMDW - ANC
2 stops22h 25mDelta
Sat 6/158:00 amANC - MDW
2 stops21h 48mDelta
Deal found 5/7$422
Sat 6/89:28 amMDW - ANC
2 stops27h 12mDelta
Thu 6/131:20 amANC - MDW
2 stops28h 28mDelta
Deal found 5/7$426
Fri 6/71:24 pmMDW - ANC
1 stop12h 08mDelta
Fri 6/1411:45 pmANC - MDW
1 stop14h 19mDelta
Deal found 5/8$432
Fri 6/79:34 amMDW - ANC
2 stops27h 06mDelta
Sat 6/158:00 pmANC - MDW
1 stop18h 04mDelta
Deal found 5/7$437

Midway to Alaska flights leaving soon

Find last-minute flight options from Midway to Alaska for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Fri 5/172:15 pmMDW - ANC
1 stop9h 27mDelta
Sun 5/196:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/7$679
Fri 5/171:21 pmMDW - ANC
2 stops14h 00mDelta
Sun 5/196:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/7$684
Mon 5/137:10 pmMDW - ANC
1 stop8h 19mDelta
Tue 5/146:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/7$704
Mon 5/132:15 pmMDW - ANC
1 stop9h 27mDelta
Wed 5/156:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/7$709
Mon 5/137:10 pmMDW - ANC
1 stop8h 19mDelta
Tue 5/146:15 amANC - MDW
2 stops12h 46mDelta
Deal found 5/7$710
Wed 5/152:15 pmMDW - ANC
1 stop13h 14mDelta
Sun 5/196:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/8$745
Wed 5/151:21 pmMDW - ANC
2 stops14h 08mDelta
Sun 5/196:15 amANC - MDW
1 stop8h 52mDelta
Deal found 5/8$750
Mon 5/132:15 pmMDW - ANC
1 stop9h 27mDelta
Wed 5/156:15 amANC - MDW
2 stops12h 46mDelta
Deal found 5/7$797
Wed 5/157:10 pmMDW - ANC
1 stop8h 19mDelta
Sat 5/181:46 amANC - MDW
2 stops13h 21mDelta
Deal found 5/8$834

One-way flights to Alaska from Midway

Search for one-way flight options from Midway to Alaska. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
Thu 5/307:10 pmMDW - ANC
1 stop8h 19mDelta
Deal found 5/7$178
Thu 9/55:00 pmMDW - ANC
1 stop10h 17mDelta
Deal found 5/7$206
Thu 9/55:00 pmMDW - ANC
2 stops11h 45mDelta
Deal found 5/7$211
Fri 10/42:00 pmMDW - FAI
2 stops13h 26mDelta
Deal found 5/8$236
Wed 8/146:45 pmMDW - ANC
1 stop8h 32mDelta
Deal found 5/7$258
Wed 8/141:10 pmMDW - ANC
2 stops13h 42mDelta
Deal found 5/7$263
Thu 5/301:21 pmMDW - ANC
2 stops14h 08mDelta
Deal found 5/7$276
Sun 6/169:34 amMDW - ANC
1 stop15h 11mDelta
Deal found 5/7$295
Tue 7/301:24 pmMDW - ANC
2 stops13h 24mDelta
Deal found 5/7$336

Find flights from Midway to Alaska within your budget

Customize your flight search to find flights from Midway to Alaska that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$382 - $701

Route

Depart

Return

Price

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 5/30

1 stop8h 19m

Anchorage

Sun 6/30

1 stop15h 10m

$382

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 5/28

2 stops10h 21m

Anchorage

Sun 6/2

1 stop7h 55m

$387

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 5/29

1 stop9h 27m

Anchorage

Sun 6/2

1 stop7h 55m

$410

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 6/8

2 stops27h 12m

Anchorage

Sun 6/16

1 stop15h 09m

$415

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 9/28

1 stop10h 26m

Anchorage

Tue 10/1

2 stops13h 23m

$417

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 6/8

2 stops22h 25m

Anchorage

Sun 6/16

2 stops12h 39m

$422

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 6/8

2 stops27h 12m

Anchorage

Thu 6/13

2 stops28h 28m

$426

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 6/6

3 stops42h 09m

Anchorage

Thu 6/13

2 stops28h 07m

$628

Chicago MidwayAnchorage

MDW - ANC

MDWANC

Chicago Midway

Thu 7/4

3 stops42h 36m

Anchorage

Sun 7/7

2 stops27h 01m

$701

Flights are sorted by cheapest first

Deals found on 5/8

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Alaska

Get insights into the airlines that provide service to Alaska. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Alaska. Reviews last updated May 8, 2024.
Delta
8.1
Very good
10,789 reviews
Check prices

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.1

Boarding

8.2

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.1
Very good
10,789 reviews
Delta
8.1
Very good
10,789 reviews
Check prices

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.1

Boarding

8.2

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Midway to Alaska. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago Midway Airport to Alaska for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Alaska for under $400. The cheapest flight booked recently is on Delta for just $382, but on average you can expect to pay $439.

  • Are there last-minute flights available from Chicago Midway Airport to Alaska for under $700?

    There are currently 14+ open flights from Chicago Midway Airport to Alaska within the next 7 days for less than $700.

  • What are the most popular routes from Chicago Midway Airport to Alaska?

    The most popular route from Chicago Midway Airport to Alaska is Chicago Midway - Anchorage. You may also consider Chicago Midway - Fairbanks or Chicago Midway - Juneau Intl.

  • What does MDW to ANC mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to Anchorage Airport flight would often be abbreviated as a MDW to ANC flight. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Fairbanks Airport (FAI), Juneau Intl Airport (JNU), Ketchikan Airport (KTN), Sitka Airport (SIT), Kodiak Airport (ADQ).

  • Can I find deals for flights from Midway to Alaska that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Alaska flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Alaska with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Alaska flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Alaska that include hotel bookings?

    Yes. In addition to deals on Midway to Alaska flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Alaska?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Alaska.

  • Can I find deals for business class flights from Midway to Alaska?

    Yes. Cheapflights offers flight deals from Midway to Alaska by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Alaska that allow pets onboard?

    Many airlines flying from Midway to Alaska offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Alaska?

    Yes, you can often find last-minute deals on Midway to Alaska flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Alaska flight deals updated?

    The Chicago Midway Airport to Alaska flight deals you see on this page were last updated on 5/8.

See more FAQs

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Alternative routes for Midway to Alaska
See prices for flight routes from nearby airports that may be better suited for you.

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Top airline flying from Midway to Alaska

Discover the top airline that operate flights from Midway to Alaska. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,752,338 searches. Data last updated May 8, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$514FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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Search flights from Midway to Alaska by cabin class

Find flights from Midway to Alaska, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

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How does Cheapflights help users find flights from Midway to Alaska?

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Why should you use Cheapflights to find cheap flight tickets from Midway to Alaska?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Midway to Alaska.

Can Cheapflights find flights from Midway to Alaska with no change fees?

Need flexible booking options for your flight to Alaska from Midway? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Midway to Alaska become cheaper?

Of course! You can now track prices for flights from Midway to Alaska and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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