$140 Cheap Flights from Chicago (ORD) to Cheyenne (CYS)

View $140 flight on Wed, Dec 17, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Cheyenne, WY (CYS-Cheyenne Regional)

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Cheap Flights from Chicago to Cheyenne (ORD-CYS)

Prices were available within the past 7 days and start at $140 for one-way flights and $210 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Jan 14 - Thu, Jan 15
ORD
Chicago
CYS
Cheyenne
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jan 14 from Chicago to Cheyenne, returning Thu, Jan 15, priced at $210 found 3 days ago
United
Sat, Jan 10 - Mon, Jan 12
ORD
Chicago
CYS
Cheyenne
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Cheyenne, returning Mon, Jan 12, priced at $234 found 4 days ago
United
Wed, Jan 14 - Thu, Jan 15
ORD
Chicago
CYS
Cheyenne
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jan 14 from Chicago to Cheyenne, returning Thu, Jan 15, priced at $235 found 3 days ago
United
Sat, Jan 10 - Mon, Jan 12
ORD
Chicago
CYS
Cheyenne
$244 Roundtrip, found 4 days ago
$244
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Cheyenne, returning Mon, Jan 12, priced at $244 found 4 days ago
United
Sat, Jan 10 - Mon, Jan 12
ORD
Chicago
CYS
Cheyenne
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Cheyenne, returning Mon, Jan 12, priced at $258 found 4 days ago
United
Wed, Jan 14 - Thu, Jan 15
ORD
Chicago
CYS
Cheyenne
$259 Roundtrip, found 3 days ago
$259
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jan 14 from Chicago to Cheyenne, returning Thu, Jan 15, priced at $259 found 3 days ago
United
Sat, Jan 10 - Mon, Jan 12
ORD
Chicago
CYS
Cheyenne
$267 Roundtrip, found 4 days ago
$267
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Cheyenne, returning Mon, Jan 12, priced at $267 found 4 days ago
United
Fri, Nov 14 - Tue, Nov 18
ORD
Chicago
CYS
Cheyenne
$268 Roundtrip, found 6 hours ago
$268
Roundtrip
found 6 hours ago
Select United flight, departing Fri, Nov 14 from Chicago to Cheyenne, returning Tue, Nov 18, priced at $268 found 6 hours ago
United
Sat, Jan 10 - Mon, Jan 12
ORD
Chicago
CYS
Cheyenne
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Cheyenne, returning Mon, Jan 12, priced at $269 found 4 days ago
United
Wed, Nov 5 - Tue, Nov 11
ORD
Chicago
CYS
Cheyenne
$278 Roundtrip, found 4 days ago
$278
Roundtrip
found 4 days ago
Select United flight, departing Wed, Nov 5 from Chicago to Cheyenne, returning Tue, Nov 11, priced at $278 found 4 days ago

Alternative airports near Cheyenne

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Cheyenne Regional CYS. Cheapest and Closest option available. Average driving time to city center is 2 minutes. Flights from $309
CYS
Cheyenne Regional
CheapestClosest
Average driving time to city center2 min
Flights from $309

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS) cost?
Lock in a cheap one-way flight from $140 or cheap return flight from $210 from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS)?
January is the least expensive month to fly from ORD to CYS. Planning your trip for the off-season is often the key to landing a great deal.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS)?
To find the cheapest airline that'll fly you from ORD to CYS, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS)?
There are no daily direct flights from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to CYS?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS)?
To reach Cheyenne Regional Airport (CYS) on time, book a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS) last-minute?
Booking your ticket from ORD to CYS right before your getaway is generally more expensive. But if you're flexible with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book an ORD to CYS flight and hotel package?
Opting for an ORD to CYS flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our wide range of stays and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Cheyenne Regional Airport (CYS)?
Generally, it's possible to cancel or reschedule your ORD to CYS flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Cheyenne Regional
Airlines serving
United
Roundtrip price
$210
Distance
874 mi

Book with confidence

Chicago to Cheyenne Flights

The cheapest times to fly from Chicago to Cheyenne

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Cheyenne are during the month of January. You can find some of the cheapest flights from Chicago to Cheyenne with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Cheyenne

Sunday is one of the best days to book for cheap flights from Chicago to Cheyenne: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Cheyenne

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Cheyenne in 2025. You can also book with separate airlines for your outbound and return journeys, from $140 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Cheyenne flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Cheyenne airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Cheyenne Flights

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*Available to One Key members.