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Cheap flights from Chicago Midway Airport to Hailey from $235

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Hailey departing on 9/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Hailey (MDW-SUN)

Cheap round-trip flights

Delta Logo
1:08 pm - 9:56 pmMDW-SUN
9h 48m2 stops
Delta Logo
7:30 am - 5:35 pmSUN-MDW
9h 05m2 stops
$579Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13
Delta Logo
1:00 pm - 10:02 pmMDW-SUN
10h 02m2 stops
Delta Logo
7:30 am - 9:46 pmSUN-MDW
13h 16m2 stops
$729Delta
Find Deal
Sun, Feb 1 - Thu, Feb 5
Delta Logo
1:08 pm - 10:00 pmMDW-SUN
9h 52m2 stops
Delta Logo
7:30 am - 5:35 pmSUN-MDW
9h 05m2 stops
$799Delta
Find Deal
Wed, Sep 24 - Thu, Sep 25
Delta Logo
3:00 pm - 9:53 pmMDW-SUN
7h 53m2 stops
Delta Logo
7:30 am - 5:43 pmSUN-MDW
9h 13m2 stops
$1,069Delta
Find Deal
Sat, Oct 11 - Sun, Oct 12
Delta Logo
1:43 pm - 9:56 pmMDW-SUN
9h 13m2 stops
Delta Logo
7:30 am - 5:37 pmSUN-MDW
9h 07m2 stops
$1,085Delta
Find Deal
Thu, Sep 4 - Tue, Sep 9
Delta Logo
6:00 am - 2:37 pmMDW-SUN
9h 37m2 stops
Delta Logo
7:30 am - 5:35 pmSUN-MDW
9h 05m2 stops
$1,319Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
1:08 pm - 9:56 pmMDW-SUN
9h 48m2 stops
Delta Logo
7:30 am - 6:37 pmSUN-MDW
10h 07m2 stops
$1,510Delta
Find Deal
Fri, Sep 5 - Mon, Sep 8
Delta Logo
2:00 pm - 10:02 pmMDW-SUN
9h 02m2 stops
Delta Logo
7:30 am - 6:08 pmSUN-MDW
9h 38m2 stops
$1,649Delta
Find Deal
Thu, Feb 12 - Mon, Feb 16

Delta flights from Chicago Midway Airport to Hailey

Our best Delta deals on Chicago Midway Airport to Hailey flight tickets
Delta
Sep 9
MDW1:08 pmChicago Midway
9h 48m
2 stops
SUN9:56 pmHailey Sun Valley-Friedman
Sep 13
SUN7:30 amHailey Sun Valley-Friedman
9h 05m
2 stops
MDW5:35 pmChicago Midway
$579
Find similar
Delta
Feb 1
MDW1:00 pmChicago Midway
10h 02m
2 stops
SUN10:02 pmHailey Sun Valley-Friedman
Feb 5
SUN7:30 amHailey Sun Valley-Friedman
13h 16m
2 stops
MDW9:46 pmChicago Midway
$729
Find similar
Delta
Sep 24
MDW1:08 pmChicago Midway
9h 52m
2 stops
SUN10:00 pmHailey Sun Valley-Friedman
Sep 25
SUN7:30 amHailey Sun Valley-Friedman
9h 05m
2 stops
MDW5:35 pmChicago Midway
$799
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Hailey that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 25, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Hailey that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Tue 9/9

1:08 pm-9:56 pm

2 stops9h 48m

Hailey Sun Valley-Friedman

Sat 9/13

7:30 am-5:35 pm

2 stops9h 05m

$579

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sun 2/1

1:00 pm-10:02 pm

2 stops10h 02m

Hailey Sun Valley-Friedman

Thu 2/5

7:30 am-9:46 pm

2 stops13h 16m

$729

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 9/24

1:08 pm-10:00 pm

2 stops9h 52m

Hailey Sun Valley-Friedman

Thu 9/25

7:30 am-5:35 pm

2 stops9h 05m

$799

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Sat 10/11

3:00 pm-9:53 pm

2 stops7h 53m

Hailey Sun Valley-Friedman

Sun 10/12

7:30 am-5:43 pm

2 stops9h 13m

$1,069

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 9/4

1:43 pm-9:56 pm

2 stops9h 13m

Hailey Sun Valley-Friedman

Tue 9/9

7:30 am-5:37 pm

2 stops9h 07m

$1,085

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 10/3

6:00 am-2:37 pm

2 stops9h 37m

Hailey Sun Valley-Friedman

Sun 10/5

7:30 am-5:35 pm

2 stops9h 05m

$1,319

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 9/5

1:08 pm-9:56 pm

2 stops9h 48m

Hailey Sun Valley-Friedman

Mon 9/8

7:30 am-6:37 pm

2 stops10h 07m

$1,510

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Thu 2/12

2:00 pm-10:02 pm

2 stops9h 02m

Hailey Sun Valley-Friedman

Mon 2/16

7:30 am-6:08 pm

2 stops9h 38m

$1,649

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Wed 9/24

1:08 pm-10:00 pm

2 stops9h 52m

$235

ChicagoHailey

MDW - SUN

MDWSUN

Chicago Midway

Fri 10/10

6:23 pm-2:43 pm

2 stops21h 20m

$265

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Hailey from

How to get the cheapest flight ticket from Chicago Midway Airport to Hailey

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Hailey?

According to our data, Saturday is the cheapest day to fly to Hailey from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $469. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Hailey is Thursday, with ticket prices averaging around $659.

What is the cheapest time of day to depart on your flight to Hailey?

According to our data, the cheapest time of day to fly to Hailey is in the evening. momondo users have found flights departing from Chicago Midway Airport to Hailey in the evening for as low as $459. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $724. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Chicago Midway Airport to Hailey

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Hailey according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Hailey (MDW to SUN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Hailey

Direct flights

None
There are no direct flights from Chicago Midway Airport to Hailey. There are no popular flight routes from Chicago Midway Airport to Hailey.
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  • How far is Chicago Midway to Hailey Sun Valley-Friedman by plane?

    The straight-line distance from Chicago Midway to Hailey Sun Valley-Friedman is 1348.8 mi. By plane, this route typically takes 7h 53m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Hailey Sun Valley-Friedman Airport?

    Prices for flights from Chicago Midway Airport to Hailey Sun Valley-Friedman Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Hailey Sun Valley-Friedman Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Hailey Sun Valley-Friedman Airport.

  • What documentation or ID do you need to fly to Hailey Sun Valley-Friedman Airport?

    The necessary travel and health documents for your Hailey Sun Valley-Friedman Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Hailey?

Book flights to Hailey if you plan to visit one of these locations
Sun Valley
Ketchum
Stanley

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hailey?

It is quick and easy to find Chicago to Hailey flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Hailey that suits you.

Can I find flights from Chicago to Hailey with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Hailey flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Hailey?

Once all potential Chicago to Hailey flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Hailey right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Hailey from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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