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$395+ Cheap flights from Midway (MDW) to Hailey (SUN)

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SUN
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Midway to Hailey

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hailey (SUN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$800
(Delta)

One-way from

$395
(Delta)

Popular in

December

Cheapest in

February

Average price

$411
Provider with most accurate pricing for Chicago (CHI)-Hailey Sun Valley-Friedman flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Hailey Sun Valley-Friedman flights.
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From Chicago Midway to Hailey Sun Valley-Friedman
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One-way flight from Chicago Midway to Hailey Sun Valley-Friedman
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Highest demand for flights based on searches. 45% potential increase in price ($453 potential increase over avg. RT price).
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Cheapest flight prices on average. 27% potential price decrease ($116 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Midway to Hailey

Cheapest flights from Midway to Hailey
Explore the most affordable flight options available from Midway to Hailey. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/266:00 am
MDW
-
SUN
2 stops9h 50m
Delta
Thu 1/297:25 am
SUN
-
MDW
2 stops10h 11m
Delta
Deal found 1/13$547
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/101:26 pm
MDW
-
SUN
2 stops9h 29m
Delta
Tue 2/177:25 am
SUN
-
MDW
2 stops9h 12m
Delta
Deal found 1/14$861
This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:49 am
MDW
-
SUN
2 stops12h 04m
Delta
Sun 3/17:25 am
SUN
-
MDW
2 stops9h 12m
Delta
Deal found 1/13$961
This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/281:26 pm
MDW
-
SUN
2 stops9h 29m
Delta
Sun 2/17:25 am
SUN
-
MDW
2 stops9h 04m
Delta
Deal found 1/13$996
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:45 am
MDW
-
SUN
2 stops12h 05m
Delta
Mon 3/307:15 am
SUN
-
MDW
2 stops9h 39m
Delta
Deal found 1/14$1,130
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/121:10 pm
MDW
-
SUN
2 stops9h 40m
Delta
Sun 3/157:15 am
SUN
-
MDW
2 stops9h 39m
Delta
Deal found 1/14$1,140
This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:05 pm
MDW
-
SUN
2 stops8h 45m
Delta
Sat 3/147:15 am
SUN
-
MDW
2 stops9h 39m
Delta
Deal found 1/13$1,150
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:47 pm
MDW
-
SUN
2 stops10h 03m
Delta
Sun 3/157:15 am
SUN
-
MDW
2 stops9h 39m
Delta
Deal found 1/14$1,390
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:49 am
MDW
-
SUN
2 stops12h 04m
Delta
Mon 3/27:25 am
SUN
-
MDW
2 stops9h 20m
Delta
Deal found 1/14$1,441
This Delta deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:49 am
MDW
-
SUN
2 stops12h 04m
Delta
Sun 3/87:15 am
SUN
-
MDW
2 stops10h 25m
Delta
Deal found 1/14$1,901

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Hailey 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 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hailey that are best for you.

Fly from

Midway

Fly to

Hailey

Route

Depart

Return

Price

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Mon 1/26

6:00 am-2:50 pm

2 stops9h 50m

Hailey Sun Valley-Friedman

Thu 1/29

7:25 am-6:36 pm

2 stops10h 11m

$547

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Tue 2/10

1:26 pm-9:55 pm

2 stops9h 29m

Hailey Sun Valley-Friedman

Tue 2/17

7:25 am-5:37 pm

2 stops9h 12m

$861

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 2/25

10:49 am-9:53 pm

2 stops12h 04m

Hailey Sun Valley-Friedman

Sun 3/1

7:25 am-5:37 pm

2 stops9h 12m

$961

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 1/28

1:26 pm-9:55 pm

2 stops9h 29m

Hailey Sun Valley-Friedman

Sun 2/1

7:25 am-5:29 pm

2 stops9h 04m

$996

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 3/25

10:45 am-9:50 pm

2 stops12h 05m

Hailey Sun Valley-Friedman

Mon 3/30

7:15 am-5:54 pm

2 stops9h 39m

$1,130

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 3/12

1:10 pm-9:50 pm

2 stops9h 40m

Hailey Sun Valley-Friedman

Sun 3/15

7:15 am-5:54 pm

2 stops9h 39m

$1,140

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 3/11

2:05 pm-9:50 pm

2 stops8h 45m

Hailey Sun Valley-Friedman

Sat 3/14

7:15 am-5:54 pm

2 stops9h 39m

$1,150

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 3/26

2:05 pm-9:50 pm

2 stops8h 45m

Hailey Sun Valley-Friedman

Mon 3/30

7:15 am-5:54 pm

2 stops9h 39m

$1,390

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 3/13

12:47 pm-9:50 pm

2 stops10h 03m

Hailey Sun Valley-Friedman

Sun 3/15

7:15 am-5:54 pm

2 stops9h 39m

$1,390

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 2/25

10:49 am-9:53 pm

2 stops12h 04m

Hailey Sun Valley-Friedman

Mon 3/2

7:25 am-5:45 pm

2 stops9h 20m

$1,441

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 14 results
1
2

Best time to book a flight from Midway to Hailey

Have a flexible travel schedule? Discover the best time to fly to Hailey from Midway 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.

Related info for your journey

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

  • What airport do you fly into for flights to Hailey from Chicago Midway?

    Hailey Sun Valley-Friedman (SUN) is the airport you will fly into if you book a flight from Chicago Midway to Hailey. You should not have trouble finding flights to Sun Valley-Friedman from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Hailey airport from Chicago Midway. It is only a 1.3 mi journey from Sun Valley-Friedman (SUN) to Hailey’s city center.

  • How long is the flight from Chicago Midway Airport to Hailey?

    Delta can get you from Chicago Midway Airport to Hailey in just under 9h 50m. Your travel time can differ by up to . The distance between Chicago Midway Airport and Hailey is about 1348 mi.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Hailey?

Book flights to Hailey if you plan to visit one of these locations
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