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

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

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Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $355
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $355

Frequently asked questions

How much does a flight from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW) 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 Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW)?
is the cheapest month to fly from CYS to MDW. Traveling during an off-peak travel window is often the key to finding a great deal.
What is the cheapest airline that flies from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from CYS to MDW, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time at all.
What day of the week has the most flights from CYS to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on time, select a flight that leaves Cheyenne Regional Airport (CYS) 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 Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from CYS to MDW right before your journey is usually more expensive. However, if there's some wiggle room with your schedule, you could snag a cheap last-minute fare.
Is it cheaper to book a CYS to MDW flight and hotel package?
Securing a CYS to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our wide range of stays and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW)?
If you reserved your CYS to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Origin airport
Cheyenne Regional
Destination airport
Midway Intl.
Distance
883 mi

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Cheyenne to Chicago Flights

The cheapest times to fly from Cheyenne to Chicago

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 Cheyenne to Chicago are during the month of . You can find some of the cheapest flights from Cheyenne to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cheyenne to Chicago

Sunday is one of the best days to book for cheap flights from Cheyenne to Chicago: 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 Cheyenne to Chicago

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 Cheyenne to Chicago in 2026. 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 Cheyenne to Chicago 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 Cheyenne to Chicago 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.

 

Cheyenne to Chicago Flights

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