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Hailey

$138+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SUN
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:47 amORD - SUN
Nonstop3h 52mAmerican Airlines
Wed 12/311:09 pmSUN - ORD
Nonstop3h 34mAmerican Airlines
Deal found 12/22$457
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/299:00 amORD - SUN
Nonstop4h 12mUnited Airlines
Wed 12/3112:53 pmSUN - ORD
Nonstop3h 41mUnited Airlines
Deal found 12/21$461
This American Airlines deal was found by Cheapflights users on 12/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:47 amORD - SUN
Nonstop3h 52mAmerican Airlines
Mon 1/58:10 amSUN - ORD
1 stop8h 42mAmerican Airlines
Deal found 12/22$846
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:19 pmORD - SUN
2 stops24h 25mAlaska Airlines
Wed 12/317:26 pmSUN - ORD
2 stops15h 31mAlaska Airlines
Deal found 12/21$931
This Delta deal was found by Cheapflights users on 12/22. 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 12/3012:45 pmMDW - SUN
2 stops10h 35mDelta
Mon 1/57:25 amSUN - MDW
2 stops10h 07mDelta
Deal found 12/22$1,209
This Delta deal was found by Cheapflights users on 12/22. 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 12/299:29 amMDW - SUN
2 stops9h 33mDelta
Wed 12/317:30 amSUN - MDW
2 stops8h 49mDelta
Deal found 12/22$1,549

Find 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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$281
(American Airlines)

One-way from

$138
(Delta)

Good round-trip deal

$368 or less

Good one-way deal

$127 or less
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 (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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Price to beat on a round-trip flight from Chicago (CHI) to Hailey Sun Valley-Friedman.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Hailey Sun Valley-Friedman.
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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 December 23, 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

Mon 1/12

9:40 am-12:46 pm

Nonstop4h 06m

Hailey Sun Valley-Friedman

Thu 1/15

1:16 pm-5:51 pm

Nonstop3h 35m

$281

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Mon 2/2

9:43 am-12:49 pm

Nonstop4h 06m

Hailey Sun Valley-Friedman

Thu 2/5

1:20 pm-5:55 pm

Nonstop3h 35m

$281

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Mon 2/2

8:00 am-7:38 pm

1 stop12h 38m

Hailey Sun Valley-Friedman

Thu 2/5

11:56 am-11:50 pm

1 stop10h 54m

$300

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Sat 3/7

5:15 pm-9:53 pm

1 stop5h 38m

Hailey Sun Valley-Friedman

Wed 3/11

12:40 pm-9:34 pm

1 stop7h 54m

$301

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Mon 1/12

1:55 pm-9:55 pm

2 stops9h 00m

Hailey Sun Valley-Friedman

Thu 1/15

3:30 pm-9:52 pm

1 stop5h 22m

$306

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Wed 3/4

7:15 am-2:40 pm

1 stop8h 25m

Hailey Sun Valley-Friedman

Tue 3/10

12:40 pm-12:39 am

2 stops10h 59m

$323

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Wed 3/11

7:20 am-2:49 pm

1 stop8h 29m

Hailey Sun Valley-Friedman

Sun 3/15

2:15 pm-11:52 pm

1 stop8h 37m

$326

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Wed 3/4

9:55 am-12:57 pm

Nonstop4h 02m

Hailey Sun Valley-Friedman

Tue 3/10

1:31 pm-6:09 pm

Nonstop3h 38m

$331

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Sat 3/7

8:42 am-11:53 am

Nonstop4h 11m

Hailey Sun Valley-Friedman

Wed 3/11

2:33 pm-10:55 pm

1 stop7h 22m

$341

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Mon 1/12

1:28 pm-9:55 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Thu 1/15

7:25 am-6:32 pm

2 stops10h 07m

$650

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 30 results
1
2
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Compare providers for flights from Chicago to Hailey

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hailey in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Hailey flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Hailey flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Hailey flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Hailey flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hailey flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, July is the cheapest month in which you can book a flight from Chicago to Hailey (average of $149). Flying from Chicago to Hailey in December is currently the most expensive (average of $288). 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 December 23, 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 morning, which can drop the price by up to 62% versus a flight at noon.

Weekly flight availability from Chicago to Hailey

Explore weekly flight availability from Chicago to Hailey. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 23, 2025.

The most flights from CHI to SUN are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

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 December 23, 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
7.9
Good
8,014 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,106 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 1 inbound flight 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 $281, American Airlines can have you in Hailey from Chicago in 4h 06m. 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.

  • What are the cheapest flights from Chicago to Hailey?

    Looking at all options, your cheapest flight can be booked for $127. While the most popular route (Chicago O'Hare Intl - Hailey Sun Valley-Friedman) can be booked for $281 on average, our data indicates $248 when flying from Chicago to Hailey.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Hailey (average of $149). Flying from Chicago to Hailey in December is currently the most expensive (average of $288). 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
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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$377FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$362Average$499FlexibilityNo cancel feeOn-time69%

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