CHI - SUN

$134 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 6/10. 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.
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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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Cheap Flights from Chicago to Hailey

 
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.

Recent round-trip flight deals from Chicago to Hailey

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Hailey.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
7:40 am - 2:39 pmORD-SUN
7h 59m1 stop
Delta Logo
3:20 pm - 10:09 pmSUN-ORD
5h 49m1 stop
$267Delta
Find Deal
Tue, Jun 24 - Mon, Jun 30
Delta Logo
7:40 am - 2:39 pmORD-SUN
7h 59m1 stop
Delta Logo
3:20 pm - 10:09 pmSUN-ORD
5h 49m1 stop
$343Delta
Find Deal
Thu, Jun 12 - Thu, Jun 19
Delta Logo
7:40 am - 2:35 pmORD-SUN
7h 55m1 stop
Delta Logo
7:30 am - 4:50 pmSUN-ORD
8h 20m2 stops
$348Delta
Find Deal
Tue, Jul 15 - Sat, Jul 19
Alaska Airlines Logo
6:00 am - 9:38 amORD-SUN
28h 38m1 stop
Alaska Airlines Logo
10:20 am - 7:42 pmSUN-ORD
8h 22m1 stop
$363Alaska Airlines
Find Deal
Mon, Jun 16 - Fri, Jun 20
United Airlines Logo
7:35 pm - 10:36 pmORD-SUN
4h 01mnonstop
United Airlines Logo
8:13 am - 12:46 pmSUN-ORD
3h 33mnonstop
$489United Airlines
Find Deal
Tue, Jul 15 - Sat, Jul 19
United Airlines Logo
7:35 pm - 10:36 pmORD-SUN
4h 01mnonstop
United Airlines Logo
2:30 pm - 10:34 pmSUN-ORD
7h 04m1 stop
$499United Airlines
Find Deal
Tue, Jul 15 - Sat, Jul 19
United Airlines Logo
7:35 pm - 10:31 pmORD-SUN
3h 56mnonstop
United Airlines Logo
7:00 am - 3:05 pmSUN-ORD
7h 05m1 stop
$539United Airlines
Find Deal
Fri, Jun 13 - Fri, Jun 20
Alaska Airlines Logo
2:03 pm - 9:38 amORD-SUN
20h 35m2 stops
Alaska Airlines Logo
10:20 am - 7:42 pmSUN-ORD
8h 22m1 stop
$574Alaska Airlines
Find Deal
Mon, Jun 16 - Fri, Jun 20
United Airlines Logo
5:00 am - 9:02 pmORD-SUN
17h 02m1 stop
United Airlines Logo
8:13 am - 12:46 pmSUN-ORD
3h 33mnonstop
$638United Airlines
Find Deal
Wed, Aug 6 - Sun, Aug 10
Alaska Airlines Logo
2:03 pm - 9:38 amORD-SUN
20h 35m2 stops
Alaska Airlines Logo
10:20 am - 11:39 pmSUN-ORD
12h 19m2 stops
$648Alaska Airlines
Find Deal
Thu, Jun 12 - Thu, Jun 19
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Hailey.

Our data shows that the cheapest route for a return flight from Chicago to Hailey cost $499 and was between Chicago O'Hare Intl Airport (ORD) and Hailey (SUN). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $499.

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 Tuesday. 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 $499 on average.

Good to know

Low seasonMarch
High seasonJanuary
Cheapest flight$134
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 2% 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 $134 for a one-way ticket and $267 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 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?

    Star Alliance is the only airline alliance operating flights between Chicago and Hailey.

  • 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.

  • 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?

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

Tuesday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Hailey Sun Valley-Friedman to Chicago

Wednesday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top airline 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 8696 reviews
6.6Food
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

Information on your arrival and departure airports

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