$698 Cheap Flights from Chicago (MDW) to Cheyenne (CYS)

View $698 flight on Wed, Nov 26, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Cheyenne, WY (CYS-Cheyenne Regional)

Cheap Flights from Chicago to Cheyenne (MDW-CYS)

Prices were available within the past 7 days and start at $698 for one-way flights and $1,369 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
CYS
Cheyenne
$1,369 Roundtrip, found 2 days ago
$1,369
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Dec 7 from Chicago to Cheyenne, returning Wed, Dec 10, priced at $1,369 found 2 days ago
Delta
Fri, Nov 7 - Mon, Nov 10
MDW
Chicago
CYS
Cheyenne
$1,370 Roundtrip, found 2 days ago
$1,370
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Nov 7 from Chicago to Cheyenne, returning Mon, Nov 10, priced at $1,370 found 2 days ago
Delta
Wed, Nov 12 - Wed, Nov 19
MDW
Chicago
CYS
Cheyenne
$1,412 Roundtrip, found 4 days ago
$1,412
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 12 from Chicago to Cheyenne, returning Wed, Nov 19, priced at $1,412 found 4 days ago
Delta
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
CYS
Cheyenne
$1,432 Roundtrip, found 2 days ago
$1,432
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Dec 7 from Chicago to Cheyenne, returning Wed, Dec 10, priced at $1,432 found 2 days ago
Delta
Fri, Nov 7 - Mon, Nov 10
MDW
Chicago
CYS
Cheyenne
$1,448 Roundtrip, found 2 days ago
$1,448
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Nov 7 from Chicago to Cheyenne, returning Mon, Nov 10, priced at $1,448 found 2 days ago
Delta
Sun, Dec 7 - Wed, Dec 10
MDW
Chicago
CYS
Cheyenne
$1,522 Roundtrip, found 2 days ago
$1,522
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Dec 7 from Chicago to Cheyenne, returning Wed, Dec 10, priced at $1,522 found 2 days ago
Delta
Thu, Apr 16 - Wed, Apr 29
MDW
Chicago
CYS
Cheyenne
$1,547 Roundtrip, found 1 day ago
$1,547
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Apr 16 from Chicago to Cheyenne, returning Wed, Apr 29, priced at $1,547 found 1 day ago
Delta
Tue, Jan 6 - Tue, Jan 20
MDW
Chicago
CYS
Cheyenne
$1,567 Roundtrip, found 1 day ago
$1,567
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 6 from Chicago to Cheyenne, returning Tue, Jan 20, priced at $1,567 found 1 day ago
Delta
Tue, Jan 6 - Fri, Jan 23
MDW
Chicago
CYS
Cheyenne
$1,568 Roundtrip, found 1 day ago
$1,568
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 6 from Chicago to Cheyenne, returning Fri, Jan 23, priced at $1,568 found 1 day ago
Delta
Mon, Apr 13 - Fri, Apr 24
MDW
Chicago
CYS
Cheyenne
$1,569 Roundtrip, found 6 hours ago
$1,569
Roundtrip
found 6 hours ago
Select Delta flight, departing Mon, Apr 13 from Chicago to Cheyenne, returning Fri, Apr 24, priced at $1,569 found 6 hours 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 $1,627
CYS
Cheyenne Regional
CheapestClosest
Average driving time to city center2 min
Flights from $1,627

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS) cost?
Grab a cheap one-way flight from $698 or cheap return flight from $1,369 from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS)?
Flying in December is a great way to save, as it's the cheapest month for flights between MDW and CYS. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS)?
To find the cheapest airline that'll fly you from MDW to CYS, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS)?
Nonstop flights from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to CYS?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS)?
To reach Cheyenne Regional Airport (CYS) on time, book a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS) last-minute?
Last-minute bookings from MDW to CYS are generally more expensive. To lock in the lowest prices, start looking for flights ahead of time. That being said, if you're flexible with your travel dates, you may land a cheap fare just before your departure.
Is it cheaper to book a MDW to CYS flight and hotel package?
You'll generally save money by booking a MDW to CYS flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've chosen your ideal flights and accommodations, you can add extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Cheyenne Regional Airport (CYS)?
In most instances, you can cancel or modify your MDW to CYS flight. However, additional fees may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you want further details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Cheyenne Regional
Roundtrip price
$1,369
Distance
883 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 December. 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 $698 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.