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Hailey

$123+ Cheap flights from Chicago (CHI) 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SUN
ago. 26 — sep. 21
mar. 8/26
mar. 9/2
1 adult, Economy
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Cheap flight deals from Chicago to Hailey

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 agosto 21, 2025.

Round-trip from

$254
(Alaska Airlines)

One-way from

$123
(Delta)

Popular in

August

Cheapest in

March

Average price

$930
From Chicago (CHI) to Hailey Sun Valley-Friedman
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One-way flight from Chicago (CHI) to Hailey Sun Valley-Friedman
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Highest demand for flights based on searches. 18% potential increase in price ($125 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Hailey

Cheapest flights from Chicago to Hailey
Explore the most affordable flight options available from Chicago to Hailey. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 21, 2025.

This United Airlines deal was found by Cheapflights users on 8/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/42:53 pmORD - SUN
1 stop7h 12mUnited Airlines
mar. 9/92:25 pmSUN - ORD
1 stop7h 17mUnited Airlines
Deal found 8/21$389
This Delta deal was found by Cheapflights users on 8/19. 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. 9/247:55 amORD - SUN
1 stop5h 03mDelta
jue. 9/2512:38 pmSUN - ORD
2 stops10h 17mDelta
Deal found 8/19$415
This Delta deal was found by Cheapflights users on 8/20. 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. 9/47:45 amORD - SUN
1 stop5h 06mDelta
lun. 9/83:15 pmSUN - ORD
1 stop4h 45mDelta
Deal found 8/20$443
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/32:53 pmORD - SUN
1 stop7h 25mUnited Airlines
dom. 10/57:00 amSUN - ORD
1 stop11h 50mUnited Airlines
Deal found 8/20$474
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/209:00 amORD - SUN
Nonstop4h 12mUnited Airlines
vie. 12/262:15 pmSUN - ORD
1 stop7h 45mUnited Airlines
Deal found 8/20$579
This Delta deal was found by Cheapflights users on 8/19. 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. 9/241:08 pmMDW - SUN
2 stops9h 52mDelta
jue. 9/257:30 amSUN - MDW
2 stops10h 05mDelta
Deal found 8/19$1,059
This Delta deal was found by Cheapflights users on 8/21. 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. 9/41:43 pmMDW - SUN
2 stops9h 13mDelta
mar. 9/97:30 amSUN - MDW
2 stops10h 07mDelta
Deal found 8/21$1,099
This Delta deal was found by Cheapflights users on 8/21. 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. 11/261:00 pmMDW - SUN
2 stops9h 59mDelta
sáb. 11/297:30 amSUN - MDW
2 stops9h 37mDelta
Deal found 8/21$1,259
This Delta deal was found by Cheapflights users on 8/21. 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.
vie. 10/31:43 pmMDW - SUN
2 stops9h 17mDelta
dom. 10/57:30 amSUN - MDW
2 stops9h 05mDelta
Deal found 8/21$1,319
This Delta deal was found by Cheapflights users on 8/20. 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. 9/41:43 pmMDW - SUN
2 stops9h 13mDelta
lun. 9/87:30 amSUN - MDW
2 stops9h 07mDelta
Deal found 8/20$1,515
This Delta deal was found by Cheapflights users on 8/21. 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. 11/262:00 pmMDW - SUN
2 stops8h 59mDelta
dom. 11/307:30 amSUN - MDW
2 stops10h 06mDelta
Deal found 8/21$1,710
This Delta deal was found by Cheapflights users on 8/20. 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. 8/281:08 pmMDW - SUN
2 stops9h 48mDelta
mar. 9/27:30 amSUN - MDW
2 stops10h 07mDelta
Deal found 8/20$1,970

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 agosto 21, 2025.
Use the filters below to find and compare flights from Chicago to Hailey that are best for you.

Fly from

Chicago

Fly to

Hailey

Route

Depart

Return

Price

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

jue. 9/4

2:53 pm-9:05 pm

1 stop7h 12m

Hailey Sun Valley-Friedman

mar. 9/9

2:25 pm-10:42 pm

1 stop7h 17m

$389

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

mié. 9/24

7:55 am-11:58 am

1 stop5h 03m

Hailey Sun Valley-Friedman

jue. 9/25

12:38 pm-11:55 pm

2 stops10h 17m

$415

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

jue. 9/4

7:45 am-11:51 am

1 stop5h 06m

Hailey Sun Valley-Friedman

lun. 9/8

3:15 pm-9:00 pm

1 stop4h 45m

$443

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

vie. 10/3

2:53 pm-9:18 pm

1 stop7h 25m

Hailey Sun Valley-Friedman

dom. 10/5

7:00 am-7:50 pm

1 stop11h 50m

$474

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

mié. 9/24

1:08 pm-10:00 pm

2 stops9h 52m

Hailey Sun Valley-Friedman

jue. 9/25

7:30 am-6:35 pm

2 stops10h 05m

$1,059

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 9/4

1:43 pm-9:56 pm

2 stops9h 13m

Hailey Sun Valley-Friedman

mar. 9/9

7:30 am-6:37 pm

2 stops10h 07m

$1,099

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

vie. 10/3

1:43 pm-10:00 pm

2 stops9h 17m

Hailey Sun Valley-Friedman

dom. 10/5

7:30 am-5:35 pm

2 stops9h 05m

$1,319

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 9/4

1:43 pm-9:56 pm

2 stops9h 13m

Hailey Sun Valley-Friedman

lun. 9/8

7:30 am-5:37 pm

2 stops9h 07m

$1,515

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

jue. 8/28

1:08 pm-9:56 pm

2 stops9h 48m

Hailey Sun Valley-Friedman

mar. 9/2

7:30 am-6:37 pm

2 stops10h 07m

$1,970

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

mié. 10/22

7:50 am-2:43 pm

1 stop7h 53m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 14 results
1
2

Best time to book a flight from Chicago to Hailey

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

Cheapflights Insights

Everything you need to know about your flight from Chicago to Hailey

What is the cheapest month to book a flight from Chicago to Hailey?

Currently, April is the cheapest month in which you can book a flight from Chicago to Hailey (average of $471). Flying from Chicago to Hailey in December is currently the most expensive (average of $608). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SUN?

Find hourly flight availability from Chicago to Hailey. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 21, 2025.

When flying from Chicago to Hailey, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 37% versus a flight at noon.

Reviews of airlines servicing Hailey

Get insights into the airlines that provide service to Hailey. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hailey. Reviews last updated agosto 21, 2025.
Read through reviews of airlines operating flights from Chicago to Hailey, such as Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,930 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    Most people fly into Hailey Sun Valley-Friedman (SUN) if they book a flight to Hailey from Chicago. On average, Sun Valley-Friedman has 0 inbound flights from Chicago per day from 2 airlines. Hailey Sun Valley-Friedman is conveniently located just 1.3 mi from Hailey’s city center.

  • How long is the flight from Chicago to Hailey?

    For as low as $415, United Airlines can have you in Hailey from Chicago in 5h 03m. Airlines will cover a distance of 1337 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Hailey round-trip?

    Cheapflights users have booked flights from Chicago to Hailey round-trip from $246. Another airline that can offer you cheap pricing is United Airlines. Users have found that Delta is 54% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

  • What is the cheapest month to book a flight from Chicago to Hailey?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Hailey (average of $471). Flying from Chicago to Hailey in December is currently the most expensive (average of $608). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hailey?

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

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Alternative routes for Chicago to Hailey

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Top 2 airlines flying from Chicago to Hailey

Discover the top 2 airlines that operate flights from Chicago to Hailey. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$364Average$565FlexibilityNo cancel feeOn-time69%

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