CHI - SUN

$211 Find Cheap Flights from Chicago to Hailey

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hailey departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hailey

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hailey, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hailey, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$421
Delta
Sat 7/11Wed 7/15
ORD - SUN • 1 stop
Cheapest non-stop
$445
United Airlines
Sat 7/11Tue 7/14
ORD - SUN • Non-stop
Top airlines
Cheapest • from $421 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $453 (round-trip)
Shortest trip • 5h 45m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hailey!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hailey (CHI-SUN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hailey that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hailey

Sat, Jul 11 - Wed, Jul 15
Delta Logo
7:45 am - 2:31 pm
ORD
-
SUN
7h 46m
1 stop
Delta Logo
1:10 pm - 9:48 pm
SUN
-
ORD
7h 38m
1 stop
$421Delta
Sat, Jul 11 - Wed, Jul 15
Delta Logo
7:45 am - 2:31 pm
ORD
-
SUN
7h 46m
1 stop
Delta Logo
7:20 am - 7:30 pm
SUN
-
ORD
11h 10m
2 stops
$426Delta
Fri, Jun 12 - Tue, Jun 16
Delta Logo
11:30 am - 10:09 pm
ORD
-
SUN
11h 39m
2 stops
Delta Logo
7:20 am - 8:32 pm
SUN
-
ORD
12h 12m
2 stops
$431Delta
Fri, Jul 3 - Fri, Jul 10
Delta Logo
7:45 am - 2:34 pm
ORD
-
SUN
7h 49m
1 stop
Delta Logo
7:20 am - 6:29 pm
SUN
-
ORD
10h 09m
2 stops
$436Delta
Sat, Jul 11 - Tue, Jul 14
United Airlines Logo
4:00 pm - 6:58 pm
ORD
-
SUN
3h 58mnonstop
United Airlines Logo
8:15 am - 12:48 pm
SUN
-
ORD
3h 33mnonstop
$445United Airlines
Fri, Jun 12 - Tue, Jun 16
United Airlines Logo
4:00 pm - 6:57 pm
ORD
-
SUN
3h 57mnonstop
United Airlines Logo
2:38 pm - 10:49 pm
SUN
-
ORD
7h 11m
1 stop
$455United Airlines
Sat, Aug 22 - Sat, Aug 29
Delta Logo
6:00 am - 2:45 pm
MDW
-
SUN
9h 45m
2 stops
Delta Logo
7:30 am - 6:31 pm
SUN
-
MDW
10h 01m
2 stops
$465Delta
Sat, Jun 6 - Wed, Jun 10
Delta Logo
1:44 pm - 9:59 pm
ORD
-
SUN
9h 15m
2 stops
Delta Logo
7:20 am - 6:29 pm
SUN
-
ORD
10h 09m
2 stops
$465Delta
Sat, Aug 22 - Sat, Aug 29
United Airlines Logo
4:00 pm - 6:50 pm
ORD
-
SUN
3h 50mnonstop
United Airlines Logo
8:15 am - 12:50 pm
SUN
-
ORD
3h 35mnonstop
$469United Airlines
Fri, Jun 12 - Tue, Jun 16
United Airlines Logo
4:00 pm - 6:57 pm
ORD
-
SUN
3h 57mnonstop
United Airlines Logo
2:38 pm - 9:54 pm
SUN
-
ORD
6h 16m
1 stop
$477United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Hailey flights

Get data-powered insights and trends into flights from Chicago to Hailey to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Hailey flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Hailey costs $455 on the route between Chicago O'Hare Intl Airport (ORD) and Hailey (SUN). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Hailey?

The average price of all round-trip flights from Chicago to Hailey clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Hailey on a Sunday and more expensive on a Thursday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Fridays for better deals.

Can I save money by flying with a layover from Chicago to Hailey?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $536 on average.

Good to know

Cheapest flight$211
Flight from Chicago O'Hare Airport to Hailey

When to book flights from Chicago to Hailey

Are your dates flexible? Find out the best times to travel from Chicago to Hailey based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Hailey

  • What is the cheapest flight from Chicago to Hailey?

    In the last 3 days, the lowest price for a flight from Chicago to Hailey was $211 for a one-way ticket and $421 for a round-trip.

  • Do I need a passport to fly between Chicago and Hailey?

    No, a passport isn't needed to fly from Chicago to Hailey. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Hailey?

    On your way to Hailey, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Hailey Sun Valley-Friedman.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Hailey?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Hailey flight route.

  • Which aircraft models fly most regularly from Chicago to Hailey?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Hailey flight route.

  • Which airline alliances offer flights from Chicago to Hailey?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Hailey, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Hailey?

    You can catch a nonstop flight from Chicago to Hailey on on Friday, and Saturday.

  • Which is the best airline for flights from Chicago to Hailey, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Hailey are United Airlines and American Airlines. With an average price for the route of $481 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $352 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Hailey?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Hailey.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Hailey?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hailey from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Hailey?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Hailey with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Hailey?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Hailey from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Hailey

  • Looking for a cheap flight? 25% of our users found flights on this route for $485 or less round-trip.

Prefer to fly direct from Chicago to Hailey?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Hailey Sun Valley-Friedman.
Find which airlines fly direct from Chicago to Hailey Sun Valley-Friedman Airport, which days they fly and book direct flights.

Direct departures

Chicago to Hailey Sun Valley-Friedman

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Hailey Sun Valley-Friedman to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airlines flying from Chicago to Hailey

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hailey. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Hailey? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
8.1Crew
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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

Information on your arrival and departure airports