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$236+ Cheap flights from Midway (MDW) to Hailey (SUN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SUN
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$236
(Delta)

Popular in

January

Cheapest in

March
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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Highest demand for flights based on searches. 14% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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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 6, 2025.

This Delta deal was found by Cheapflights users on 11/5. 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 12/136:00 amMDW - SUN
2 stops9h 41mDelta
Wed 12/177:30 amSUN - MDW
2 stops9h 48mDelta
Deal found 11/5$311
This Delta deal was found by Cheapflights users on 11/5. 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 11/206:00 amMDW - SUN
2 stops9h 40mDelta
Mon 11/241:06 pmSUN - MDW
2 stops9h 34mDelta
Deal found 11/5$591
This Delta deal was found by Cheapflights users on 11/6. 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 11/216:00 amMDW - SUN
2 stops9h 40mDelta
Tue 11/257:30 amSUN - MDW
2 stops9h 48mDelta
Deal found 11/6$967

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 6, 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

Tue 1/27

6:00 am-2:42 pm

2 stops9h 42m

Hailey Sun Valley-Friedman

Wed 2/4

7:25 am-5:32 pm

2 stops9h 07m

$236

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sat 12/13

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

$311

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Tue 1/27

1:28 pm-9:55 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Tue 2/3

3:24 pm-8:54 am

2 stops16h 30m

$329

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Tue 4/28

10:35 am-9:54 pm

2 stops12h 19m

Hailey Sun Valley-Friedman

Thu 4/30

1:20 pm-8:42 am

2 stops18h 22m

$450

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 11/20

6:00 am-2:40 pm

2 stops9h 40m

Hailey Sun Valley-Friedman

Mon 11/24

1:06 pm-11:40 pm

2 stops9h 34m

$591

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 1/30

1:28 pm-9:55 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Tue 2/3

7:25 am-6:36 pm

2 stops10h 11m

$643

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 3/4

10:53 am-9:55 pm

2 stops12h 02m

Hailey Sun Valley-Friedman

Tue 3/10

7:30 am-6:08 pm

2 stops9h 38m

$869

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 2/4

10:46 am-9:55 pm

2 stops12h 09m

Hailey Sun Valley-Friedman

Sun 2/8

7:25 am-6:36 pm

2 stops10h 11m

$869

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Mon 11/24

1:15 pm-9:59 pm

2 stops9h 44m

$494

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Mon 11/24

6:20 am-9:37 am

3 stops28h 17m

$1,000

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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 42m. 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?

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