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$143+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SUN
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$386
(Delta)

One-way from

$143
(Delta)
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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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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/23. 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.
Sat 12/61:14 pmMDW - SUN
2 stops9h 50mDelta
Tue 12/97:30 amSUN - MDW
2 stops9h 48mDelta
Deal found 11/23$386
This Delta deal was found by Cheapflights users on 11/24. 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 12/126:00 amMDW - SUN
2 stops9h 41mDelta
Mon 12/151:06 pmSUN - MDW
2 stops9h 41mDelta
Deal found 11/24$400
This Delta deal was found by Cheapflights users on 11/24. 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 12/126:00 amMDW - SUN
2 stops9h 41mDelta
Sun 12/147:30 amSUN - MDW
2 stops9h 48mDelta
Deal found 11/24$605
This Delta deal was found by Cheapflights users on 11/24. 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.
Sun 12/146:00 amMDW - SUN
2 stops9h 41mDelta
Wed 12/177:30 amSUN - MDW
2 stops9h 48mDelta
Deal found 11/24$660
This Delta deal was found by Cheapflights users on 11/25. 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 12/269:50 amMDW - SUN
2 stops13h 30mDelta
Sat 1/37:30 amSUN - MDW
2 stops8h 49mDelta
Deal found 11/25$2,501

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 November 26, 2025.
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

Sat 12/6

1:14 pm-10:04 pm

2 stops9h 50m

Hailey Sun Valley-Friedman

Tue 12/9

7:30 am-6:18 pm

2 stops9h 48m

$386

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 12/12

6:00 am-2:41 pm

2 stops9h 41m

Hailey Sun Valley-Friedman

Mon 12/15

1:06 pm-11:47 pm

2 stops9h 41m

$400

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sun 2/1

6:00 am-2:50 pm

2 stops9h 50m

Hailey Sun Valley-Friedman

Fri 2/6

7:25 am-5:29 pm

2 stops9h 04m

$510

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Tue 2/24

1:26 pm-9:53 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Fri 2/27

7:25 am-6:37 pm

2 stops10h 12m

$533

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 12/12

6:00 am-2:41 pm

2 stops9h 41m

Hailey Sun Valley-Friedman

Sun 12/14

7:30 am-6:18 pm

2 stops9h 48m

$605

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sun 12/14

6:00 am-2:41 pm

2 stops9h 41m

Hailey Sun Valley-Friedman

Wed 12/17

7:30 am-6:18 pm

2 stops9h 48m

$660

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 3/4

10:53 am-9:53 pm

2 stops12h 00m

Hailey Sun Valley-Friedman

Tue 3/10

7:15 am-6:40 pm

2 stops10h 25m

$1,099

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 1/15

11:21 am-9:55 pm

2 stops11h 34m

Hailey Sun Valley-Friedman

Mon 1/19

7:25 am-5:55 pm

2 stops9h 30m

$1,479

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 1/23

1:26 pm-9:55 pm

2 stops9h 29m

Hailey Sun Valley-Friedman

Sun 1/25

7:25 am-5:55 pm

2 stops9h 30m

$1,580

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 1/9

1:28 pm-9:55 pm

2 stops9h 27m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 13 results
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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

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