$129 Cheap Flights from Cheyenne (CYS) to Chicago (ORD)

View $129 flight on Sat, May 31, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Cheyenne to Chicago (CYS-ORD)

Prices were available within the past 7 days and start at $129 for one-way flights and $206 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Aug 20 - Wed, Aug 27
CYS
Cheyenne
ORD
Chicago
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 20 from Cheyenne to Chicago, returning Wed, Aug 27, priced at $206 found 1 day ago
United
Fri, May 9 - Tue, May 13
CYS
Cheyenne
ORD
Chicago
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select United flight, departing Fri, May 9 from Cheyenne to Chicago, returning Tue, May 13, priced at $222 found 4 days ago
United
Sat, May 10 - Mon, May 12
CYS
Cheyenne
ORD
Chicago
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Select United flight, departing Sat, May 10 from Cheyenne to Chicago, returning Mon, May 12, priced at $248 found 2 days ago
United
Sat, May 31 - Sat, Jun 14
CYS
Cheyenne
ORD
Chicago
$262 Roundtrip, found 3 days ago
$262
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 31 from Cheyenne to Chicago, returning Sat, Jun 14, priced at $262 found 3 days ago
United
Sat, May 17 - Thu, Jun 5
CYS
Cheyenne
ORD
Chicago
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 17 from Cheyenne to Chicago, returning Thu, Jun 5, priced at $266 found 3 days ago
United
Sat, May 17 - Fri, May 30
CYS
Cheyenne
ORD
Chicago
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select United flight, departing Sat, May 17 from Cheyenne to Chicago, returning Fri, May 30, priced at $267 found 2 days ago
United
Fri, May 16 - Fri, May 30
CYS
Cheyenne
ORD
Chicago
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select United flight, departing Fri, May 16 from Cheyenne to Chicago, returning Fri, May 30, priced at $269 found 2 days ago
United
Tue, Jun 24 - Fri, Jul 4
CYS
Cheyenne
ORD
Chicago
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jun 24 from Cheyenne to Chicago, returning Fri, Jul 4, priced at $270 found 3 days ago
United
Wed, Aug 20 - Wed, Aug 27
CYS
Cheyenne
ORD
Chicago
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 20 from Cheyenne to Chicago, returning Wed, Aug 27, priced at $273 found 1 day ago
United
Wed, Aug 20 - Wed, Aug 27
CYS
Cheyenne
ORD
Chicago
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 20 from Cheyenne to Chicago, returning Wed, Aug 27, priced at $276 found 1 day ago
Flights from Cheyenne (CYS) to Chicago (ORD)
Origin airport
Cheyenne Regional
Destination airport
O'Hare Intl.
Airlines serving
United
Roundtrip price
$206
Distance
874 mi

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 August. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $129 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.

Frequently asked questions

How much does a flight from Cheyenne Regional Airport (CYS) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from CYS to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from CYS to ORD?
The cheapest flights from CYS to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from CYS to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from CYS to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Cheyenne Regional Airport (CYS) to O'Hare Intl. Airport (ORD)?
You’ll have to hop on a flight with a layover if you’re traveling from Cheyenne Regional Airport (CYS) to O’Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from CYS to ORD?
You’ll typically find Tuesday the quietest day for flights, while Fridays tend to be 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 O'Hare Intl. Airport (ORD)?
Book a flight from Cheyenne Regional Airport (CYS) to O’Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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 O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book your flight from CYS to ORD often results in higher prices. While you might find some last-minute discounts, there’s no guarantee. Keep your travel plans flexible to maximize your chances of getting a bargain.
Is it cheaper to book a CYS to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a CYS to ORD flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one convenient place will take the hassle out of planning your trip. Just secure your flights and select from our extensive range of stays, then customize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Cheyenne Regional Airport (CYS) to O'Hare Intl. Airport (ORD)?
Usually, it’s possible to reschedule or cancel your CYS to ORD flight. However, if it’s been more than 24 hours since booking, additional charges may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find more information on our Customer Service portal.

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*Available to One Key members.