What is the cheapest month to book a flight from Alaska to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Alaska to Chicago Midway Airport (average of $160). Flying from Alaska to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

How far in advance should I book a flight from Alaska to Chicago Midway Airport?

To save on the cost of your flight from Alaska to Chicago Midway Airport, book at least 43 days before your planned departure. Booking around this time can save you about 142% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $619 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $678.

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

Our data shows that November tends to be the cheapest month to fly to Chicago Midway Airport from Alaska. Users have commonly found prices around $522 for the month, but tickets can be as low as $212. Due to multiple factors, prepare for potentially higher prices in March.

What is the cheapest time of day to fly from AK to MDW?

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

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

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

How can I find direct flights from Alaska to Midway?

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

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

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

$168+ Flights from Alaska to Chicago Midway Airport

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Cheap flight deals from Alaska to Midway

Round-trip from	$338 (Delta)
One-way from	$168 (Delta)
Popular in	March
Cheapest in	November
Average price	$586

From Alaska to Chicago Midway

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One-way flight from Alaska to Chicago Midway

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Highest demand for flights based on searches. 14% potential increase in price ($84 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Find flight deals from Alaska to Midway

Cheapest flights from Alaska to Midway
Explore the most affordable flight options available from Alaska to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Fri 9/510:30 pmANC - MDW

1 stop10h 58mDelta

Sun 9/79:31 amMDW - ANC

1 stop14h 24mDelta

Deal found 7/30

$338

Sat 9/131:50 amFAI - MDW

2 stops12h 45mDelta

Sat 9/279:35 amMDW - FAI

2 stops18h 15mDelta

Deal found 7/31

$751

Best flights from Alaska to Midway
Discover carefully curated flight deals from Alaska to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2025.

Fri 9/510:30 pmANC - MDW

1 stop10h 58mDelta

Sun 9/71:08 pmMDW - ANC

1 stop10h 47mDelta

Deal found 7/31

$338

Sat 9/131:50 amFAI - MDW

2 stops12h 45mDelta

Sat 9/279:35 amMDW - FAI

2 stops18h 15mDelta

Deal found 7/31

$751

Last-minute flights from Alaska to Midway
Discover last-minute flight deals from Alaska to Midway. Data last updated July 31, 2025 and is based on user searches.

Tue 8/1210:07 pmFAI - MDW

1 stop7h 43mDelta

Sat 8/161:43 pmMDW - FAI

1 stop10h 12mDelta

Deal found 7/31

$867

Thu 8/216:00 amANC - MDW

1 stop8h 37mDelta

Wed 8/279:30 amMDW - ANC

1 stop14h 25mDelta

Deal found 7/31

$338

One-way flights from Alaska to Midway
Search for one-way flight options from Alaska to Midway. Find affordable one-way fares based on user searches. Data last updated July 31, 2025.

Sun 8/316:00 amANC - MDW

1 stop8h 37mDelta

Deal found 7/30

$168

Fri 8/2910:07 pmFAI - MDW

1 stop10h 27mDelta

Deal found 7/30

$239

Thu 8/141:20 pmANC - MDW

3 stops25h 57mMultiple Airlines

Deal found 7/30

$419

Cheapflights Fare Finder

Use the filters below to find and compare flights from Alaska to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/5

10:30 pm-12:28 pm

1 stop10h 58m

Chicago Midway

Sun 9/7

1:08 pm-8:55 pm

1 stop10h 47m

$338

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sat 9/13

1:50 am-5:35 pm

2 stops12h 45m

Chicago Midway

Sat 9/27

9:35 am-12:50 am

2 stops18h 15m

$751

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 8/31

6:00 am-5:37 pm

1 stop8h 37m

$168

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Fri 8/29

10:07 pm-11:34 am

1 stop10h 27m

$239

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 8/14

1:20 pm-6:17 pm

3 stops25h 57m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Best time to book a flight from Alaska to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Alaska with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Alaska to Chicago Midway Airport

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

Reviews of airlines servicing Midway

Peruse reviews from past customers who have flown with Delta from Alaska to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,981 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Can I find deals for flights from Alaska to Midway that include hotel bookings?
Yes. In addition to deals on Alaska to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Alaska to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Alaska to Midway.
Can I find deals for business class flights from Alaska to Midway?
Yes. Cheapflights offers flight deals from Alaska to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Alaska to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Alaska to Chicago Midway Airport (average of $160). Flying from Alaska to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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$168+ Cheap flights from Alaska to Midway (MDW)

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Alaska to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Alaska to Midway

Keep the following information in mind while searching for Alaska to Midway flight deals. Data was last updated July 31, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Alaska to Midway

Cheapest flights from Alaska to MidwayExplore the most affordable flight options available from Alaska to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Explore the most affordable flight options available from Alaska to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Alaska to Chicago Midway Airport that are best for you.

Best time to book a flight from Alaska to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Alaska with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Alaska to Chicago Midway Airport

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 31, 2025.

Peruse reviews from past customers who have flown with Delta from Alaska to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

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

How can I find direct flights from Alaska to Midway?

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

What is the cheapest month to book a flight from Alaska to Chicago Midway Airport?

Traveling to a place near Chicago Midway Airport?

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Alternative routes for Alaska to Midway

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Cheapest flights from Alaska to Midway
Explore the most affordable flight options available from Alaska to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.