CHI - SUN

$133 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 11/11. 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

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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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

Wed, Mar 4 - Tue, Mar 10
Delta Logo
7:15 am - 2:52 pmORD-SUN
8h 37m1 stop
Delta Logo
3:25 pm - 9:55 pmSUN-ORD
5h 30m1 stop
$265Delta
Find Deal
Thu, Oct 30 - Sat, Nov 1
Delta Logo
7:50 am - 2:43 pmORD-SUN
7h 53m1 stop
Delta Logo
7:30 am - 1:56 pmSUN-ORD
5h 26m1 stop
$285Delta
Find Deal
Thu, Oct 30 - Sat, Nov 1
Delta Logo
7:50 am - 2:43 pmORD-SUN
7h 53m1 stop
Delta Logo
12:49 pm - 9:43 pmSUN-ORD
7h 54m1 stop
$289Delta
Find Deal
Thu, Oct 30 - Sat, Nov 1
Delta Logo
7:50 am - 2:43 pmORD-SUN
7h 53m1 stop
Delta Logo
7:30 am - 4:50 pmSUN-ORD
8h 20m2 stops
$290Delta
Find Deal
Wed, Mar 4 - Tue, Mar 10
American Airlines Logo
9:40 am - 12:30 pmORD-SUN
3h 50mnonstop
American Airlines Logo
1:30 pm - 5:50 pmSUN-ORD
3h 20mnonstop
$325American Airlines
Find Deal
Sat, Feb 28 - Tue, Mar 3
United Airlines Logo
9:00 am - 11:59 amORD-SUN
3h 59mnonstop
United Airlines Logo
2:29 pm - 10:52 pmSUN-ORD
7h 23m1 stop
$326United Airlines
Find Deal
Wed, Mar 4 - Tue, Mar 10
American Airlines Logo
1:16 pm - 8:10 pmORD-SUN
7h 54m1 stop
American Airlines Logo
1:30 pm - 5:50 pmSUN-ORD
3h 20mnonstop
$335American Airlines
Find Deal
Sat, Feb 28 - Tue, Mar 3
United Airlines Logo
2:45 pm - 9:11 pmORD-SUN
7h 26m1 stop
United Airlines Logo
2:29 pm - 10:52 pmSUN-ORD
7h 23m1 stop
$336United Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Alaska Airlines Logo
6:20 am - 9:34 amORD-SUN
28h 14m1 stop
Alaska Airlines Logo
10:16 am - 7:48 pmSUN-ORD
8h 32m1 stop
$437Alaska Airlines
Find Deal
Sat, Feb 28 - Tue, Mar 3
Alaska Airlines Logo
2:05 pm - 6:30 pmORD-SUN
29h 25m2 stops
Alaska Airlines Logo
7:15 pm - 5:04 amSUN-ORD
8h 49m1 stop
$447Alaska Airlines
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $265 (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
Cheapest round-trip
$265
Delta
Wed 3/4Tue 3/10
ORD - SUN • 1 stop
Cheapest non-stop
$325
American Airlines
Wed 3/4Tue 3/10
ORD - SUN • Non-stop
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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!
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 $269 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.

No, with an average price for the route of $469, prices are generally cheapest when you fly direct.

Good to know

Low seasonMarch
Cheapest flight$133
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 17% 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 $133 for a one-way ticket and $265 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, oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Hailey, with oneworld 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 $392 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 $569 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.

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 $269 or less round-trip.

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 7954 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

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.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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

Information on your arrival and departure airports

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