Cheap flights from Chicago to Hailey

Flight deals from Chicago to Hailey

Below you can see the best deals on flights Chicago — Hailey for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 9 September, from $303.

Top 10 cheap flights from Chicago to Hailey

About the Chicago — Hailey flight

Looking for cheap flights from Chicago to Hailey? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Hailey ticket online at the best price.

The route has direct flights — around 2 flights per week, flights are operated by United Airlines, a nonstop flight takes about 3 h 58 min, the distance between the cities is around 2,185 km.

Planning your trip? You may find our Hailey travel guide, how to get from the airport into town and Hailey weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

from $169Min. price

JanuaryCheapest

SeptemberPeak season

YesDirect flights

2,185 kmDistance

3 h 58 minTravel time

1Airlines

2 / wkFlights

Flight schedule from Chicago to Hailey

The table shows direct flights from Chicago to Hailey on the selected date. The flight takes approximately 3 h 58 min. Regular flights are operated by United Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Friedman Memorial Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Wed, 9 September

Any time

Last update: 08 Sep 2026

Airline

Flight

Departure

Arrival

Duration

Days

Status

Below is a calendar of the lowest flight ticket prices for Chicago — Hailey by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $169 in January, and the most expensive are around $303 in September. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

Prices by month

Average one-way fares from Chicago to Hailey by month. Tickets are usually cheapest in October (around $291) and priciest in December (about $478) — use the table and chart below to pick the best time to fly.

Month	Average price	Level	Month	Average price	Level	Month	Average price	Level
Jan	$443	high	May	$315	low	Sep	$303	low
Feb	$431	high	Jun	$373	medium	Oct	$291	low
Mar	$408	high	Jul	$419	high	Nov	$350	medium
Apr	$338	low	Aug	$384	medium	Dec	$478	high

Some values are estimated based on seasonality.

When to fly

Weather in Hailey: it is warmest in July (up to 26 °C on average) and coolest in January (around -3 °C). The driest month is July.

Tickets are usually cheapest in January and most expensive in September. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Hailey

Dry and wet days · Hailey

Wind speed and direction · Hailey

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How to get the best deal on a Chicago — Hailey ticket

Book ahead: fares for Chicago — Hailey are usually lower 3–8 weeks before departure than at the last minute.
Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
Chicago is served by more than one airport — compare fares and travel time to each before you book.
The cheapest month to fly to Hailey is usually January — plan your trip around it if your dates are flexible.
Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Flights on the Chicago — Hailey route are operated by 1 airline; United Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

United AirlinesUA
1x/week
WebsiteFleet: 956165M pax/year
- Direct flight ORD → SUN1x/week
100.0%Open →

Cities and airports on the Chicago — Hailey route

Flights Chicago — Hailey depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Friedman Memorial Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI

United States

About the city How to get there Weather All about the country United States

Arrival

Hailey

SUN

United States

About the city How to get there Weather All about the country United States

Departure airports

O'Hare International AirportORD
About the airport
Chicago Midway International AirportMDW
About the airport
Midway International AirportNOH
About the airport
Chicago Rockford International AirportRFD
About the airport

Arrival airports

Friedman Memorial AirportSUN
About the airport

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Frequently asked questions about the Chicago — Hailey flight

How long is the flight from Chicago to Hailey?

A nonstop Chicago — Hailey flight takes about 3 h 58 min — the distance between the cities is around 2,185 km.

How far is it from Chicago to Hailey?

The distance from Chicago to Hailey is about 2,185 km, which a nonstop flight covers in around 3 h 58 min.

Are there direct flights from Chicago to Hailey?

Yes, there are nonstop flights Chicago — Hailey — around 2 flights per week.

Which airlines fly from Chicago to Hailey?

Airlines operating Chicago — Hailey include United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Hailey flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Friedman Memorial Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Hailey?

The price of a Chicago — Hailey ticket depends on your travel date, season and demand: it is usually cheapest to fly in January, and most expensive in September. Tickets typically cost between $169 and $303. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Hailey?

Flights Chicago — Hailey are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is January. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Hailey?

To catch a low fare Chicago — Hailey, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually January.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Hailey

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