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MDW - ANC

$230 Find Cheap Flights from Chicago Midway Airport to Anchorage - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$459
Typical prices: $358-$525
Delta
Wed 10/24Wed 10/31
MDW - ANC • 1 stop
Cheapest one-way
$230
Typical prices: $220-$365
Delta
Wed 12/5
MDW - ANC • 1 stop
When to travel
February
Cheapest • 31% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Minneapolis St Paul (MSP)
Cheapest • Avg $399 (round-trip)
Denver Intl (DEN)
Shortest trip • 9h 32m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Midway to Anchorage (MDW-ANC)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Anchorage

Sat, Dec 5 - Wed, Dec 9
Delta Logo
10:24 am - 8:53 pmMDW  Chicago Midway-ANC Anchorage
13h 29m1 stop Minneapolis St Paul
Delta Logo
10:05 pm - 8:55 amANC  Anchorage-MDW Chicago Midway
7h 50m1 stop Minneapolis St Paul
$459Delta
Sat, Oct 24 - Sat, Oct 31
Delta Logo
12:27 pm - 8:59 pmMDW  Chicago Midway-ANC Anchorage
11h 32m1 stop Minneapolis St Paul
Delta Logo
10:17 pm - 9:44 amANC  Anchorage-MDW Chicago Midway
8h 27m1 stop Minneapolis St Paul
$459Delta
Sat, Nov 14 - Tue, Nov 17
Delta Logo
12:30 pm - 8:58 pmMDW  Chicago Midway-ANC Anchorage
11h 28m1 stop Minneapolis St Paul
Delta Logo
10:08 pm - 8:50 amANC  Anchorage-MDW Chicago Midway
7h 42m1 stop Minneapolis St Paul
$459Delta
Sat, Dec 5 - Tue, Dec 8
Delta Logo
10:24 am - 8:53 pmMDW  Chicago Midway-ANC Anchorage
13h 29m1 stop Minneapolis St Paul
Delta Logo
10:05 pm - 8:55 amANC  Anchorage-MDW Chicago Midway
7h 50m1 stop Minneapolis St Paul
$459Delta
Sat, Oct 31 - Sat, Nov 7
Delta Logo
10:12 am - 8:59 pmMDW  Chicago Midway-ANC Anchorage
13h 47m1 stop Minneapolis St Paul
Delta Logo
10:09 pm - 11:47 amANC  Anchorage-MDW Chicago Midway
10h 38m1 stop Minneapolis St Paul
$459Delta
Wed, Dec 2 - Tue, Dec 8
Delta Logo
9:37 am - 11:28 pmMDW  Chicago Midway-ANC Anchorage
16h 51m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
10:05 pm - 11:59 amANC  Anchorage-MDW Chicago Midway
10h 54m1 stop Minneapolis St Paul
$464Delta
Sat, Oct 24 - Sat, Oct 31
Delta Logo
12:27 pm - 12:35 amMDW  Chicago Midway-ANC Anchorage
15h 08m2 stops Minneapolis St Paul Seattle/Tacoma Intl
Delta Logo
10:17 pm - 9:44 amANC  Anchorage-MDW Chicago Midway
8h 27m1 stop Minneapolis St Paul
$464Delta
Sat, Dec 5 - Tue, Dec 8
Delta Logo
1:41 pm - 11:28 pmMDW  Chicago Midway-ANC Anchorage
12h 47m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
10:05 pm - 11:59 amANC  Anchorage-MDW Chicago Midway
10h 54m1 stop Minneapolis St Paul
$464Delta
Wed, Dec 2 - Sat, Dec 5
Delta Logo
9:37 am - 1:45 amMDW  Chicago Midway-ANC Anchorage
19h 08m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
10:05 pm - 8:55 amANC  Anchorage-MDW Chicago Midway
7h 50m1 stop Minneapolis St Paul
$464Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Anchorage flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Anchorage?

Round-trip flights from Chicago Midway Airport to Anchorage typically range from $358 to $525. The lowest price found in the past 5 days was $459, on Delta.

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Key details for Chicago Midway Airport to Anchorage flights

Low season

October

Cheapest flight

$230
One-way flight from Chicago Midway Airport to Anchorage

When to book flights from Midway to Anchorage

Are your dates flexible? Find out the best times to travel from Midway to Anchorage based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Anchorage flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Anchorage?

    Only Economy Class is available on flights from Chicago Midway Airport to Anchorage.

  • How long is a flight from Chicago Midway Airport to Anchorage?

    There are currently no nonstop flights available from Chicago Midway Airport to Anchorage. Flights with 1 layover take between 9h 32m and 11h 02m in total, depending on the connection.

  • Do I need a passport to fly from Chicago Midway Airport to Anchorage?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • Have flight prices from Chicago Midway Airport to Anchorage changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $459 to $3,371. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Anchorage looking right now?

    One-way fares from Chicago Midway Airport to Anchorage are currently in line with typical prices for this route. Average one-way fares are about $247.

  • What car rental options are available at Anchorage Airport (ANC)?

    Anchorage Airport (ANC) hosts 5 major car rental companies, with daily rates starting from around $34 for economy cars. Top options include:

    • Budget
    • Avis
    • NextCar
    • Alamo
    • Dollar

  • Which airports can I use when flying from Chicago Midway Airport to Anchorage?

    Flights from Chicago Midway Airport to Anchorage usually depart from Chicago Midway (MDW) and arrive at Anchorage (ANC).

  • Which airports do connecting flights from Chicago Midway Airport to Anchorage pass through?

    Connecting flights from Chicago Midway Airport to Anchorage most commonly pass through:

    • Minneapolis St Paul (MSP) - 75% of one-stop connections
    • Denver Intl (DEN) - 25% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Anchorage?

    Yes. Flexible dates can save you up to 53% on flights from Chicago Midway Airport to Anchorage. Friday is the cheapest departure day at $357 round-trip on average, while Saturday is the most expensive at $749, a difference of $392.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Anchorage?

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 9h 32m, compared with 11h 02m via Minneapolis St Paul (MSP).

  • What is the time difference between Chicago Midway Airport and Anchorage?

    Anchorage is 3 hours behind Chicago Midway Airport (Alaska Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Anchorage?

    Some of the most popular sights in Anchorage are Alaska Railroad Depot, Dena'ina Civic and Convention Center and William A. Egan Civic & Convention Center. These are among the most viewed places in Anchorage on KAYAK.

Your guide to booking Chicago Midway Airport to Anchorage flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Friday departure and avoid flying on Saturday. On this route, Friday flights average $357, about $392 less than Saturday fares (52% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Anchorage trip for February. Fares historically average $295 round-trip in that month - typically $454 less than the most expensive month, which is June (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Anchorage Airport.

    • Wyndham Garden Anchorage Airport
    • The Lakefront Anchorage
    • Alex Hotel and Suites Anchorage Airport

More options for your flight from Midway to Anchorage

Complete your trip to Anchorage with a hotel stay or car rental

Car rentals in Anchorage
Hotels in Anchorage
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