Cheap Flights from Chicago to Cheyenne

Compare Chicago to Cheyenne flight deals

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

Book the best Cheyenne fare with no extra fees

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 March.

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 foundج.م.‏ 11,621
Cheapest month to flyMarch

Finding cheap flights from Chicago to Cheyenne: Frequently asked questions

The best price we found for a return flight from Chicago to Cheyenne is ج.م.‏ 12,812. 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 ج.م.‏ 12,812.
As of February 2026, there are no flights flying from Chicago to Cheyenne.
The cheapest month to fly from Chicago to Cheyenne is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Cheyenne Airport on Saturday, 7 March 2026.
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 .

Travelling from Chicago to Cheyenne Regional Airport (CYS): What you need to know

  • Begin your trip planning by checking out the best place to catch your flight from Chicago to Cheyenne Regional Airport (CYS). Explore your options for leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), the city's main airports.

  • Cheyenne Regional Airport is located in Cheyenne. The city is in the UTC-6 timezone and is one hour behind Chicago.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Make sure you're at the airport on time to catch your flight from Chicago to CYS.

  • Peak travel periods mean busier airports, so be there even earlier. Give yourself at least two hours before a domestic flight and four hours for an international journey to stick to your schedule.

Airports in Chicago

O'Hare International Airport (ORD)

  • ORD is about 40 kilometres from central Chicago. If you're ride-sharing, catching a cab or driving from the centre, it'll take 35 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 55 minutes.

  • Want an easy start to your journey? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Cheyenne Regional Airport or aren't a fan of being rushed, these hotels are the ideal choice:

  • 74.85% of flights that take off from O'Hare International Airport touch down at their destination on schedule.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can reach MDW from the centre of Chicago in about 20 minutes by car (depending on traffic conditions). The ride by public transport will take roughly 45 minutes to travel the 19 kilometres or so.

  • Flying out early in the morning? Think about staying at one of these accommodation options near Chicago Midway International Airport the day before your Chicago to CYS flight:

  • When it comes to flight punctuality, Chicago Midway International Airport has an on-time arrival rate of 77.88%.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From central Chicago, RFD is around 137 kilometres away. It'll take you roughly 1 hour 25 minutes to get there by car and 4 hours 15 minutes or so if you take public transport.

  • Rest a little longer, move a little slower, and still make your Chicago to Cheyenne Regional Airport flight with plenty of time to spare. These accommodation options near Chicago Rockford International Airport make departure day effortless if you're jetting off early:

  • The on-time performance record of RFD is 76.19%. To put it simply, that's how frequently flights that depart this airport arrive at their destination as planned.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Cheyenne Regional Airport (CYS)

Getting from Cheyenne Regional Airport (CYS) to central Cheyenne

  • Cheyenne Regional Airport to central Cheyenne is roughly 2 kilometres. If you're renting a car or getting a cab, plan ahead to make your trip as easy as possible. Journey times may vary depending on the time of day and traffic conditions.

  • Travelling on public transport takes around 35 minutes.

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

  • The cheapest price we've found for a one-way ticket from Chicago to Cheyenne Regional Airport is ج.م.‏ 11,621. For a return flight on this route, the best price is ج.م.‏ 12,812. Depending on when you book and the availability, these fares could change.

  • Booking in advance is often the key to scoring a cheap flight from Chicago to CYS. Prices tend to rise as demand increases, so the closer you get to departure, the more you'll likely spend.

  • The 'Whole month' tool shows you the cheapest Chicago to Cheyenne Regional Airport tickets across each month. It's a great way to find a bargain if your plans aren't set in stone.

  • There's no need to check back in every day to find out if prices have dropped when you set up a Price Alert. We'll notify you when a better deal comes up on flight tickets from Chicago to CYS.

  • Tailor your flights using filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago to Cheyenne Regional Airport.

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

  • October is when most people book flights from Chicago to Cheyenne Regional Airport (CYS). Visit Cheyenne in February for a more low-key escape.

  • Before locking in your Chicago to CYS flight ticket, consider the kind of weather you prefer. July is the warmest month in Cheyenne, with temperatures ranging from 13ºC to 30ºC.

  • February has temperatures of between -9ºC and 6ºC. Search for cheap tickets from Chicago to Cheyenne Regional Airport around that time if you want to travel when it's cooler.

More about Cheyenne

Explore more of the United States

  • You've visited Cheyenne, now it's time to discover other corners of the United States. Travel around 161 kilometres south to Denver to tick off its top attractions. From Denver Art Museum to Meow Wolf Denver | Convergence Station and Ballpark, your itinerary will be busy.

  • Colorado Springs is another well-known destination in the United States and is around 257 kilometres south of Cheyenne. No journey is complete without dropping by Garden of the Gods, Pikes Peak Region Attractions and Red Rock Canyon.

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