$190 Find Cheap Flights from Chicago Midway Airport to Alaska

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Alaska departing on 9/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Alaska

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Alaska, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Alaska, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Alaska Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Anchorage
Anchorage1 stop$372
Fairbanks
Fairbanks2 stops$288
Anchorage
Anchorage1 stop$372
Fairbanks
Fairbanks2 stops$288

Cheap Flights from Midway to Alaska

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Alaska 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 Midway to Alaska

Tue, Aug 5 - Mon, Aug 11
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
10:07 pm - 5:37 pmFAI-MDW
16h 30m1 stop
$288Delta
Find Deal
Tue, Aug 5 - Mon, Aug 11
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
1:50 am - 5:37 pmFAI-MDW
36h 47m2 stops
$296Delta
Find Deal
Tue, Aug 5 - Sun, Aug 10
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
1:50 am - 5:37 pmFAI-MDW
36h 47m2 stops
$316Delta
Find Deal
Tue, Aug 5 - Fri, Aug 15
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
10:07 pm - 5:37 pmFAI-MDW
16h 30m1 stop
$324Delta
Find Deal
Tue, Aug 5 - Fri, Aug 15
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
3:15 pm - 5:37 pmFAI-MDW
23h 22m2 stops
$329Delta
Find Deal
Tue, Aug 5 - Thu, Aug 14
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
3:15 pm - 8:50 amFAI-MDW
38h 35m2 stops
$332Delta
Find Deal
Tue, Aug 5 - Thu, Aug 14
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
10:07 pm - 5:37 pmFAI-MDW
16h 30m1 stop
$353Delta
Find Deal
Wed, Aug 6 - Mon, Aug 11
Delta Logo
9:24 am - 2:22 pmMDW-FAI
31h 58m2 stops
Delta Logo
1:50 am - 5:37 pmFAI-MDW
36h 47m2 stops
$361Delta
Find Deal
Tue, Aug 5 - Wed, Aug 13
Delta Logo
1:46 pm - 12:50 amMDW-FAI
38h 04m2 stops
Delta Logo
1:50 am - 5:37 pmFAI-MDW
36h 47m2 stops
$364Delta
Find Deal
Sat, Sep 20 - Sun, Sep 21
Delta Logo
6:45 pm - 1:00 amMDW-ANC
9h 15m1 stop
Delta Logo
6:10 am - 6:07 pmANC-MDW
8h 57m1 stop
$372Delta
Find Deal
Useful Info

KAYAK's insights & trends for Midway to Alaska flights

Get data-powered insights and trends into flights from Midway to Alaska to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Chicago Midway Airport to Alaska take?

The duration of a flight to Alaska depends on your arrival airport. The shortest routes to Alaska from Chicago Midway Airport are to Anchorage, which takes 8h 46m, Juneau, which takes 11h 40m, and Ketchikan, which takes 12h 53m.


Good to know

Cheapest flight$190
Flight from Chicago Midway Airport to Anchorage

FAQs - booking Alaska flights

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

    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 Chicago Midway Airport to Alaska.

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

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

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

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

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

  • What is the cheapest time of day to fly to Alaska?

    The cheapest time of day to fly to Alaska is generally in the afternoon, when round-trip flights cost $514 on average. Morning departures are around 50% cheaper than evening flights, on average. The most expensive time of day to fly to Alaska is generally in the evening, which is peak travel time and where the average cost of a ticket is $1,182.

Top airline flying from Midway to Alaska

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Alaska. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Alaska? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7963 reviews
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
7.3Food
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

Everything you need to know for your flight from Midway to Alaska

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.