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 2/24. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$301
Delta
ג' 2/24ש' 2/28
ORD - SUN • 1 stop
Cheapest non-stop
$375
American Airlines
ו' 3/20ג' 3/24
ORD - SUN • Non-stop
Top airlines
Delta
Cheapest • from $301 (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
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

ג', פב​​​​​​​' 24 - ש', פב​​​​​​​' 28
Delta Logo
7:15 am - 12:01 pm
ORD
-
SUN
5h 46m
1 stop
Delta Logo
12:41 pm - 9:52 pm
SUN
-
ORD
8h 11m
1 stop
$301Delta
ג', פב​​​​​​​' 10 - ש', פב​​​​​​​' 14
Delta Logo
7:20 am - 2:50 pm
ORD
-
SUN
8h 30m
1 stop
Delta Logo
12:41 pm - 9:52 pm
SUN
-
ORD
8h 11m
1 stop
$351Delta
ג', פב​​​​​​​' 10 - ש', פב​​​​​​​' 14
Delta Logo
5:30 am - 2:50 pm
ORD
-
SUN
10h 20m
2 stops
Delta Logo
12:41 pm - 9:52 pm
SUN
-
ORD
8h 11m
1 stop
$356Delta
ג', פב​​​​​​​' 24 - ש', פב​​​​​​​' 28
Delta Logo
7:15 am - 12:01 pm
ORD
-
SUN
5h 46m
1 stop
Delta Logo
12:41 pm - 11:52 pm
SUN
-
ORD
10h 11m
2 stops
$367Delta
ו', מרץ 20 - ג', מרץ 24
American Airlines Logo
9:50 am - 12:54 pm
ORD
-
SUN
4h 04mnonstop
American Airlines Logo
1:27 pm - 6:00 pm
SUN
-
ORD
3h 33mnonstop
$375American Airlines
ג', פב​​​​​​​' 10 - ש', פב​​​​​​​' 14
American Airlines Logo
9:43 am - 12:49 pm
ORD
-
SUN
4h 06mnonstop
American Airlines Logo
1:27 pm - 6:00 pm
SUN
-
ORD
3h 33mnonstop
$381American Airlines
ג', פב​​​​​​​' 10 - ש', פב​​​​​​​' 14
American Airlines Logo
9:43 am - 12:49 pm
ORD
-
SUN
4h 06mnonstop
American Airlines Logo
7:40 am - 5:47 pm
SUN
-
ORD
9h 07m
1 stop
$391American Airlines
ג', פב​​​​​​​' 10 - ש', פב​​​​​​​' 14
Delta Logo
1:58 pm - 9:55 pm
ORD
-
SUN
8h 57m
2 stops
Delta Logo
12:41 pm - 11:56 pm
SUN
-
ORD
10h 15m
2 stops
$402Delta
ד', פב​​​​​​​' 25 - ב', מרץ 2
Alaska Airlines Logo
7:00 am - 6:22 pm
ORD
-
SUN
12h 22m
1 stop
Alaska Airlines Logo
7:04 pm - 2:11 pm
SUN
-
ORD
18h 07m
1 stop
$435Alaska Airlines
ו', מרץ 20 - ג', מרץ 24
Delta Logo
7:25 am - 1:31 pm
ORD
-
SUN
7h 06m
1 stop
Delta Logo
12:40 pm - 9:34 pm
SUN
-
ORD
7h 54m
1 stop
$440Delta
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 $296 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 Monday. 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 $411 on average.

Good to know

Low seasonMarch
Cheapest flight$156
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 36% lower on average.
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 $301 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?

    There are nonstop flights from Chicago to Hailey on a daily basis.

  • 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 $483 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 $245 or less one-way and $331 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

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 3 airlines serving 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 8119 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
7.9Comfort
Airline reviews

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

10.0 ExcellentSenthil Kumar, Jan 2026
PDX - ATL
Read more Delta reviews

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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

Information on your arrival and departure airports