CHI - SUN

$156 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 1/27. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$281
American Airlines
Sun 1/18Fri 1/23
ORD - SUN • Non-stop
Cheapest one-way
$156
Alaska Airlines
Tue 1/27
ORD - SUN • 1 stop
Top airlines
American Airlines
Cheapest • from $281 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-SUN
Cheapest
ORD-SUN
Most popular
Insights
Insights
Insights
Insights
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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

Sun, Jan 18 - Fri, Jan 23
American Airlines Logo
12:15 pm - 3:23 pmORD-SUN
4h 08mnonstop
American Airlines Logo
1:16 pm - 5:51 pmSUN-ORD
3h 35mnonstop
$281American Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23
American Airlines Logo
10:57 am - 8:17 pmORD-SUN
10h 20m1 stop
American Airlines Logo
1:16 pm - 5:51 pmSUN-ORD
3h 35mnonstop
$291American Airlines
Find Deal
Fri, Jan 9 - Tue, Jan 13
Alaska Airlines Logo
6:06 pm - 11:14 amORD-SUN
18h 08m1 stop
Alaska Airlines Logo
11:56 am - 11:55 pmSUN-ORD
10h 59m1 stop
$300Alaska Airlines
Find Deal
Tue, Jan 6 - Thu, Jan 15
Delta Logo
7:20 am - 2:42 pmORD-SUN
8h 22m1 stop
Delta Logo
12:43 pm - 9:52 pmSUN-ORD
8h 09m1 stop
$301Delta
Find Deal
Thu, Jan 8 - Fri, Jan 16
Delta Logo
7:20 am - 2:42 pmORD-SUN
8h 22m1 stop
Delta Logo
12:43 pm - 11:57 pmSUN-ORD
10h 14m2 stops
$306Delta
Find Deal
Wed, Jan 7 - Wed, Jan 14
Delta Logo
1:28 pm - 9:55 pmMDW-SUN
9h 27m2 stops
Delta Logo
7:25 am - 5:34 pmSUN-MDW
9h 09m2 stops
$311Delta
Find Deal
Wed, Jan 7 - Wed, Jan 14
Delta Logo
1:54 pm - 9:55 pmORD-SUN
9h 01m2 stops
Delta Logo
12:43 pm - 11:57 pmSUN-ORD
10h 14m2 stops
$311Delta
Find Deal
Fri, Jan 9 - Tue, Jan 13
United Airlines Logo
8:45 am - 12:02 pmORD-SUN
4h 17mnonstop
United Airlines Logo
12:43 pm - 5:24 pmSUN-ORD
3h 41mnonstop
$325United Airlines
Find Deal
Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
8:45 am - 12:02 pmORD-SUN
4h 17mnonstop
United Airlines Logo
12:43 pm - 5:24 pmSUN-ORD
3h 41mnonstop
$361United Airlines
Find Deal
Sun, Jan 4 - Mon, Jan 5
Alaska Airlines Logo
7:00 am - 6:44 pmORD-SUN
12h 44m2 stops
Alaska Airlines Logo
7:26 pm - 6:29 amSUN-ORD
10h 03m1 stop
$398Alaska Airlines
Find Deal
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 $385 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 Wednesday 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 $331 on average.

Good to know

Low seasonMarch
Cheapest flight$156
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 26% increase in price.
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 $156 for a one-way ticket and $281 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Hailey are Delta and United Airlines. With an average price for the route of $388 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $527 and an overall rating of 7.4.

  • 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.

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

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Hailey Sun Valley-Friedman to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American 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.
7.9
DeltaOverall score based on 7992 reviews
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

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

Information on your arrival and departure airports

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