MDW

$188 Find Cheap Flights from Alaska to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 9/1. 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
1 adult, Economy

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Flights Deals

Cheap Flights from Alaska to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Alaska to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Alaska to Midway

Tue, Oct 14 - Thu, Oct 16
Delta Logo
6:10 am - 6:07 pmANC-MDW
8h 57m1 stop
Delta Logo
9:30 am - 11:15 pmMDW-ANC
16h 45m2 stops
$415Delta
Find Deal
Mon, Oct 13 - Thu, Oct 16
Delta Logo
12:40 am - 6:36 pmANC-MDW
14h 56m2 stops
Delta Logo
9:30 am - 11:15 pmMDW-ANC
16h 45m2 stops
$420Delta
Find Deal
Thu, Aug 14 - Fri, Aug 22
Delta Logo
5:19 pm - 8:35 amANC-MDW
12h 16m2 stops
Delta Logo
1:08 pm - 8:55 pmMDW-ANC
10h 47m1 stop
$421Delta
Find Deal
Thu, Aug 14 - Fri, Aug 22
Delta Logo
5:19 pm - 8:35 amANC-MDW
12h 16m2 stops
Delta Logo
1:08 pm - 11:27 pmMDW-ANC
13h 19m2 stops
$426Delta
Find Deal
Fri, Aug 22 - Sun, Aug 24
Delta Logo
10:30 pm - 12:28 pmANC-MDW
10h 58m1 stop
Delta Logo
1:08 pm - 8:55 pmMDW-ANC
10h 47m1 stop
$449Delta
Find Deal
Tue, Oct 14 - Thu, Oct 16
Delta Logo
6:10 am - 6:07 pmANC-MDW
8h 57m1 stop
Delta Logo
2:00 pm - 7:49 pmMDW-ANC
8h 49m1 stop
$450Delta
Find Deal
Mon, Oct 13 - Thu, Oct 16
Delta Logo
12:40 am - 6:36 pmANC-MDW
14h 56m2 stops
Delta Logo
6:45 pm - 1:00 amMDW-ANC
9h 15m1 stop
$455Delta
Find Deal
Fri, Aug 15 - Mon, Aug 18
Delta Logo
10:07 pm - 1:03 pmFAI-MDW
11h 56m1 stop
Delta Logo
1:08 pm - 12:50 amMDW-FAI
14h 42m2 stops
$484Delta
Find Deal
Fri, Aug 22 - Sun, Aug 24
Delta Logo
5:19 pm - 8:35 amANC-MDW
12h 16m2 stops
Delta Logo
1:08 pm - 8:55 pmMDW-ANC
10h 47m1 stop
$484Delta
Find Deal
Mon, Jul 14 - Mon, Jul 21
Delta Logo
10:35 pm - 12:29 pmANC-MDW
10h 54m1 stop
Delta Logo
9:25 am - 8:58 pmMDW-ANC
14h 33m1 stop
$492Delta
Find Deal
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$188
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Anchorage to Chicago Midway Airport

FAQs for booking Alaska to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Alaska to Chicago Midway Airport?

    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 Alaska to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Alaska to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Alaska 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 Alaska to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Alaska with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Alaska to Chicago Midway Airport?

    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 Chicago Midway Airport from Alaska up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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