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$412+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SUN
feb. 3 — feb. 101
mar. 2/3
mar. 2/10
1 adult, Economy
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Cheap 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 enero 4, 2026.

This Delta deal was found by Cheapflights users on 1/3. 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.
lun. 1/191:26 pmMDW - SUN
2 stops9h 29mDelta
vie. 1/237:25 amSUN - MDW
2 stops10h 11mDelta
Deal found 1/3$412
This Delta deal was found by Cheapflights users on 1/3. 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.
lun. 1/121:28 pmMDW - SUN
2 stops9h 27mDelta
jue. 1/157:25 amSUN - MDW
2 stops10h 07mDelta
Deal found 1/3$501
This Delta deal was found by Cheapflights users on 1/2. 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.
mié. 3/41:29 pmMDW - SUN
2 stops9h 24mDelta
mar. 3/107:15 amSUN - MDW
2 stops10h 25mDelta
Deal found 1/2$830
This Delta deal was found by Cheapflights users on 1/2. 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.
sáb. 6/61:00 pmMDW - SUN
2 stops9h 54mDelta
jue. 6/117:30 amSUN - MDW
2 stops9h 35mDelta
Deal found 1/2$980
This Delta deal was found by Cheapflights users on 1/4. 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.
mié. 2/251:26 pmMDW - SUN
2 stops9h 27mDelta
dom. 3/17:25 amSUN - MDW
2 stops9h 12mDelta
Deal found 1/4$1,130
This Delta deal was found by Cheapflights users on 1/2. 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.
mar. 2/241:26 pmMDW - SUN
2 stops9h 27mDelta
sáb. 2/286:55 pmSUN - MDW
2 stops13h 11mDelta
Deal found 1/2$1,203
This Delta deal was found by Cheapflights users on 1/2. 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.
dom. 5/311:00 pmMDW - SUN
2 stops9h 54mDelta
dom. 6/77:30 amSUN - MDW
2 stops9h 35mDelta
Deal found 1/2$1,210
This Delta deal was found by Cheapflights users on 1/2. 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.
jue. 2/2610:49 amMDW - SUN
2 stops12h 04mDelta
dom. 3/17:25 amSUN - MDW
2 stops9h 12mDelta
Deal found 1/2$1,290
This Delta deal was found by Cheapflights users on 1/2. 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.
lun. 7/201:00 pmMDW - SUN
2 stops9h 54mDelta
dom. 7/267:30 amSUN - MDW
2 stops13h 16mDelta
Deal found 1/2$1,340
This Delta deal was found by Cheapflights users on 1/1. 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.
jue. 2/191:26 pmMDW - SUN
2 stops9h 27mDelta
dom. 2/227:25 amSUN - MDW
2 stops9h 20mDelta
Deal found 1/1$1,621
This Delta deal was found by Cheapflights users on 1/3. 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.
jue. 2/126:00 amMDW - SUN
2 stops9h 40mDelta
lun. 2/167:25 amSUN - MDW
2 stops10h 15mDelta
Deal found 1/3$2,031

Find 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 enero 4, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$412
(Delta)

One-way from

$221
(Delta)

Popular in

December

Cheapest in

February

Average price

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

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 enero 4, 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

lun. 1/19

1:26 pm-9:55 pm

2 stops9h 29m

Hailey Sun Valley-Friedman

vie. 1/23

7:25 am-6:36 pm

2 stops10h 11m

$412

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

mié. 3/4

1:29 pm-9:53 pm

2 stops9h 24m

Hailey Sun Valley-Friedman

mar. 3/10

7:15 am-6:40 pm

2 stops10h 25m

$830

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

sáb. 6/6

1:00 pm-9:54 pm

2 stops9h 54m

Hailey Sun Valley-Friedman

jue. 6/11

7:30 am-6:05 pm

2 stops9h 35m

$980

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

mié. 2/25

1:26 pm-9:53 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

dom. 3/1

7:25 am-5:37 pm

2 stops9h 12m

$1,130

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

mar. 2/24

1:26 pm-9:53 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

sáb. 2/28

6:55 pm-9:06 am

2 stops13h 11m

$1,203

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

dom. 5/31

1:00 pm-9:54 pm

2 stops9h 54m

Hailey Sun Valley-Friedman

dom. 6/7

7:30 am-6:05 pm

2 stops9h 35m

$1,210

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 2/26

10:49 am-9:53 pm

2 stops12h 04m

Hailey Sun Valley-Friedman

dom. 3/1

7:25 am-5:37 pm

2 stops9h 12m

$1,290

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 2/19

1:26 pm-9:53 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

dom. 2/22

7:25 am-5:45 pm

2 stops9h 20m

$1,621

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 2/12

6:00 am-2:40 pm

2 stops9h 40m

Hailey Sun Valley-Friedman

lun. 2/16

7:25 am-5:37 pm

2 stops9h 12m

$2,031

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 2/12

6:00 am-2:40 pm

2 stops9h 40m

$785

Flights are sorted by cheapest round-trip flights first.

Deals found on 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 29m. 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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