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

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

Flights from Chicago (MDW) to Cheyenne (CYS)
Origin airport
Midway Intl.
Destination airport
Cheyenne Regional
Distance
883 mi

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 . 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 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.

 

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 or cheap return flight 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 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.

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*Available to One Key members.