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Hailey

$156+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SUN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$281
(American Airlines)

One-way from

$156
(Alaska Airlines)

Popular in

January

Cheapest in

March
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
Search Deals
One-way flight from Chicago (CHI) 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).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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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 October 30, 2025.

This Expedia deal was found by Cheapflights users on 10/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1210:00 amORD - SUN
1 stop25h 08mAlaska Airlines
Tue 12/1610:50 amSUN - ORD
1 stop10h 40mAlaska Airlines
Deal found 10/30$300
This Delta deal was found by Cheapflights users on 10/30. 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 12/127:20 amORD - SUN
1 stop8h 21mDelta
Tue 12/161:06 pmSUN - ORD
2 stops8h 37mDelta
Deal found 10/30$306
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:00 amORD - SUN
1 stop8h 00mDelta
Thu 1/812:43 pmSUN - ORD
1 stop8h 09mDelta
Deal found 10/29$345
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 12/309:00 amORD - SUN
Nonstop4h 12mUnited Airlines
Wed 1/712:43 pmSUN - ORD
Nonstop3h 41mUnited Airlines
Deal found 10/29$361
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 12/309:00 amORD - SUN
Nonstop4h 12mUnited Airlines
Thu 1/82:31 pmSUN - ORD
1 stop8h 27mUnited Airlines
Deal found 10/29$371
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:00 amORD - SUN
1 stop8h 00mDelta
Wed 1/77:25 amSUN - ORD
1 stop5h 13mDelta
Deal found 10/29$374
This Delta deal was found by Cheapflights users on 10/29. 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 11/137:20 amORD - SUN
1 stop6h 06mDelta
Mon 11/177:30 amSUN - ORD
2 stops10h 22mDelta
Deal found 10/29$376
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/319:00 amORD - SUN
Nonstop4h 12mUnited Airlines
Wed 1/712:43 pmSUN - ORD
Nonstop3h 41mUnited Airlines
Deal found 10/29$405
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/319:00 amORD - SUN
Nonstop4h 12mUnited Airlines
Thu 1/82:31 pmSUN - ORD
1 stop5h 44mUnited Airlines
Deal found 10/29$415
This Delta deal was found by Cheapflights users on 10/29. 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 11/136:00 amMDW - SUN
2 stops9h 40mDelta
Mon 11/171:06 pmSUN - MDW
2 stops9h 34mDelta
Deal found 10/29$501
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/319:50 amMDW - SUN
2 stops13h 30mDelta
Sun 1/47:30 amSUN - MDW
2 stops8h 49mDelta
Deal found 10/29$1,980

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 October 30, 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

Sun 1/18

12:15 pm-3:23 pm

Nonstop4h 08m

Hailey Sun Valley-Friedman

Fri 1/23

1:16 pm-5:51 pm

Nonstop3h 35m

$281

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Wed 3/4

7:15 am-2:52 pm

1 stop8h 37m

Hailey Sun Valley-Friedman

Tue 3/10

3:25 pm-9:55 pm

1 stop5h 30m

$301

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Sun 1/18

7:20 am-12:03 pm

1 stop5h 43m

Hailey Sun Valley-Friedman

Fri 1/23

12:43 pm-9:52 pm

1 stop8h 09m

$301

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Fri 1/9

7:20 am-2:42 pm

1 stop8h 22m

Hailey Sun Valley-Friedman

Wed 1/14

7:25 am-5:56 pm

2 stops9h 31m

$306

ChicagoHailey

ORD - SUN

ORDSUN

Chicago O'Hare Intl

Fri 12/12

7:20 am-2:41 pm

1 stop8h 21m

Hailey Sun Valley-Friedman

Tue 12/16

1:06 pm-10:43 pm

2 stops8h 37m

$306

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sat 1/10

11:21 am-9:55 pm

2 stops11h 34m

Hailey Sun Valley-Friedman

Mon 1/12

7:25 am-5:34 pm

2 stops9h 09m

$311

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sun 1/11

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

$311

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Mon 1/12

1:28 pm-9:55 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Tue 1/13

7:25 am-6:32 pm

2 stops10h 07m

$311

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 1/7

1:28 pm-9:55 pm

2 stops9h 27m

Hailey Sun Valley-Friedman

Mon 1/12

7:25 am-5:34 pm

2 stops9h 09m

$311

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sat 1/10

11:21 am-9:55 pm

2 stops11h 34m

Hailey Sun Valley-Friedman

Tue 1/13

7:25 am-6:32 pm

2 stops10h 07m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 31 results
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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 October.
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 January is currently the most expensive (average of $271). 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 October 30, 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 54% 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 October 30, 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
7,998 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 $281, American Airlines can have you in Hailey from Chicago in 4h 08m. 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 47% 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, 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 January is currently the most expensive (average of $271). 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$382FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$362Average$588FlexibilityNo cancel feeOn-time69%

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