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

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Compare Chicago to Cheyenne flight deals

Find the cheapest month or even day of the year to fly to Cheyenne

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Find the cheapest month to fly from Chicago to Cheyenne

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Cheyenne flights are currently cheapest in August.

Chicago to Cheyenne: Alternative routes

Compare routes from Chicago to Cheyenne below. You may find an airport to fly into that's cheaper, faster, or easier than Cheyenne.

Chicago to Cheyenne: Flight information

The things to know before you go.
Cheapest flight found$130
Cheapest month to flyAugust

Finding cheap flights from Chicago to Cheyenne: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Cheyenne is $248. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Cheyenne. But we found flights with one stop from $248.
There are no flights flying from Chicago to Cheyenne, as of May 2025.
The cheapest month to fly from Chicago to Cheyenne is usually May 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Cheyenne Airport on Friday, June 13, 2025.
No airlines currently offer direct flights between Chicago and Cheyenne Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Cheyenne but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Cheyenne is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Cheyenne is United.

Traveling from Chicago to Cheyenne Regional Airport (CYS): what you need to know

  • Countless great adventures start at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Check out your options for booking a flight from Chicago to Cheyenne Regional Airport (CYS) taking off from either of these bases.

  • The timezone in Cheyenne is UTC-6, which is 1 hour behind Chicago. Cheyenne Regional Airport is located in Cheyenne.

  • Leave plenty of time to get on your flight from Chicago to CYS. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • With more travelers during peak months like August, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will allow extra time for delays. Remember things also get busy during major holidays like Christmas and local events or festivals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

About Cheyenne Regional Airport (CYS)

Getting from Cheyenne Regional Airport (CYS) to central Cheyenne

  • Cheyenne Regional Airport is approximately 2 miles from the center of Cheyenne. With a cab or in your own car rental, the drive is about 7 minutes.

  • Traveling to the center by public transport will take you around 33 minutes.

How to find the cheapest flights from Chicago to Cheyenne Regional Airport (CYS)

  • $130 is the cheapest price we've seen for a one-way ticket from Chicago to Cheyenne Regional Airport. Return flights start from $248. Prices may vary depending on availability at the time of booking.

  • Don't leave everything to the last minute. You're more likely to get cheap tickets from Chicago to CYS if you book early. Airlines often have some great early bird deals.

  • Finding cheap tickets from Chicago to Cheyenne Regional Airport is more likely if you can be flexible with your trip dates. Try using the 'Whole month' search tool to see the lowest prices across every month and snap up a great deal.

  • Snapping up a cheap ticket from Chicago to CYS is a piece of cake with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as the price has fallen.

  • Make the most of the filters to find your ideal trip. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Chicago to Cheyenne Regional Airport, use the 'Sort by' tool. You can also filter results by departure and arrival times, airline, and number of stops.

The best time to fly from Chicago to Cheyenne Regional Airport (CYS)

  • October is the busiest month to hop on a flight from Chicago to Cheyenne Regional Airport while February is the quietest. To work out the best time to visit Cheyenne, consider the pace you prefer to travel at.

  • The warmest month in Cheyenne is July, with the temperature ranging between 55ºF and 86ºF. Lock in your flights from Chicago to CYS in this month if you enjoy this type of weather.

  • Travel in February if you want cooler conditions. Temperatures average between 16ºF and 43ºF. However, this city promises a good time whenever you book your cheap flights from Chicago to Cheyenne Regional Airport.

More about Cheyenne

  • When it comes to looking for somewhere to rest your head, you'll find the top stays in Cheyenne right here. Browse these options after you've booked your flight from Chicago to Cheyenne Regional Airport:

  • Every great journey has to include some sightseeing. Cheyenne Frontier Days, Cheyenne Depot Museum and Nelson Museum of the West are essential stops on your Cheyenne itinerary.

Complete your Cheyenne trip with a car rental

  • Finding you a cheap flight from Chicago to Cheyenne Regional Airport isn't our only party trick. Check out our car rentals in Cheyenne and explore the city on your own terms. We find deals from trusted car rental providers and put them all in one place. Instantly compare offers and then book with no fees.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.