CHI - SUN

$176 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 4/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$345
United Airlines
Thu 4/2Fri 4/10
ORD - SUN • Non-stop
Cheapest non-stop
$355
American Airlines
Fri 3/27Fri 4/3
ORD - SUN • Non-stop
Top airlines
Cheapest • from $345 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 4h 04m
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 $383 (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

Thu, Apr 2 - Fri, Apr 10
United Airlines Logo
8:40 am - 11:44 am
ORD
-
SUN
4h 04mnonstop
United Airlines Logo
2:24 pm - 11:28 pm
SUN
-
ORD
8h 04m
1 stop
$345United Airlines
Fri, Mar 27 - Fri, Apr 3
American Airlines Logo
9:50 am - 12:54 pm
ORD
-
SUN
4h 04mnonstop
American Airlines Logo
1:26 pm - 5:59 pm
SUN
-
ORD
3h 33mnonstop
$355American Airlines
Fri, Apr 10 - Mon, Apr 13
Delta Logo
7:20 am - 2:49 pm
ORD
-
SUN
8h 29m
1 stop
Delta Logo
3:34 pm - 9:18 pm
SUN
-
ORD
4h 44m
1 stop
$361Delta
Fri, Apr 10 - Mon, Apr 13
Delta Logo
8:55 am - 2:49 pm
ORD
-
SUN
6h 54m
2 stops
Delta Logo
12:42 pm - 9:18 pm
SUN
-
ORD
7h 36m
1 stop
$366Delta
Sun, Mar 29 - Wed, Apr 1
American Airlines Logo
9:55 am - 12:59 pm
ORD
-
SUN
4h 04mnonstop
American Airlines Logo
1:27 pm - 6:00 pm
SUN
-
ORD
3h 33mnonstop
$371American Airlines
Sat, Apr 11 - Tue, Apr 14
United Airlines Logo
8:40 am - 1:35 pm
ORD
-
SUN
5h 55m
1 stop
United Airlines Logo
2:24 pm - 9:20 pm
SUN
-
ORD
5h 56m
1 stop
$375United Airlines
Sat, Apr 4 - Tue, Apr 7
United Airlines Logo
8:40 am - 11:44 am
ORD
-
SUN
4h 04mnonstop
United Airlines Logo
2:24 pm - 9:20 pm
SUN
-
ORD
5h 56m
1 stop
$383United Airlines
Wed, Jul 29 - Mon, Aug 3
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
$384United Airlines
Fri, Apr 17 - Mon, Apr 20
Delta Logo
7:35 am - 12:01 pm
ORD
-
SUN
5h 26m
1 stop
Delta Logo
12:42 pm - 11:58 pm
SUN
-
ORD
10h 16m
2 stops
$388Delta
Fri, Apr 17 - Mon, Apr 20
Delta Logo
7:35 am - 12:01 pm
ORD
-
SUN
5h 26m
1 stop
Delta Logo
3:34 pm - 9:18 pm
SUN
-
ORD
4h 44m
1 stop
$390Delta
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 $243 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 $411 on average.

Good to know

Low seasonMarch
Cheapest flight$186
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 37% 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 $186 for a one-way ticket and $345 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 $481 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 $272 or less one-way and $281 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 8288 reviews
8.5Crew
7.2Food
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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

Information on your arrival and departure airports