$126 Cheap Flights from Chicago (ORD) to Cheyenne (CYS)
Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Cheyenne, WY (CYS-Cheyenne Regional)
UnitedUnited
Cheap Flights from Chicago to Cheyenne (ORD-CYS)
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Chicago (ORD) to Cheyenne (CYS) at a glance
Travel from Chicago O'Hare International Airport (ORD) to Cheyenne Regional Airport (CYS) with ease on this short domestic route. Discover the best itinerary that aligns with your travel plans as you delve into Cheyenne's renowned attractions and neighborhoods. Check out essential information for your upcoming Chicago to Cheyenne flights, including various options and airfares to Cheyenne (CYS).
- Fastest flight duration: around 3h 30m in-flight, plus roughly 1h 45m layover with one stop
- Route distance: roughly 900 miles (1,450 km)
- Flights per week: around 7 departures on average
- Typical fares (one-way): economy tickets often range from $120–$625, depending on seasonality and how far ahead you book
Flights from O'Hare International Airport (ORD) to Cheyenne Regional Airport (CYS)
According to recent traveler bookings, here are the top airlines favored for flights from Chicago to Cheyenne, typically featuring one-stop services. Many routes include a popular layover at Denver International Airport (DEN), which lasts about 1 hour and 45 minutes. This flexibility allows you to compare prices, total travel times, and cabin classes to craft your ideal itinerary.
- United: This comprehensive carrier provides a seamless travel experience, dominating the departures on this route. One-way ticket prices typically range from $120 to $625, with an in-flight duration of 3 hours and 30 minutes. Expect a total travel time of approximately 5 hours and 30 minutes, including layover time.
Alternative route from Chicago (ORD) to Cheyenne (CYS)
- Chicago to Laramie (ORD-LAR): Located approximately 46 miles from Cheyenne Regional Airport (CYS), Laramie Regional Airport (LAR) serves as a convenient destination. On this route, one-way economy fares generally fall between $125 and $415, influenced by the season and the timing of your booking. Most flights are typically one-stop journeys, with Denver International Airport (DEN) as the primary connection hub. United Airlines is the leading carrier for this route.
How to find the best prices for flights from Chicago (ORD) to Cheyenne (CYS)
Getting some of the best deals on flights from Chicago to Cheyenne is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are typically available when booking 2 to 8 weeks in advance, although most travelers tend to book within 2 weeks. Departures in the morning, from 5 AM to 12 PM, not only offer lower prices but are also the most popular flight times. Additionally, flying on Tuesday provides both affordable options and is the most favored travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Cheyenne hotel and flight deals.
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at Cheyenne Regional Airport from O'Hare International Airport
Cheyenne welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Cheyenne efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Cheyenne, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
- Car rental: Renting a car from Cheyenne Regional Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Cheyenne Regional Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
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 March. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $126 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 Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) cost?
You can find cheap one-way flights from $126 and cheap return flights $290 Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) with Expedia. One-way flights generally range between $102 and $833, and roundtrip flights usually range from $388 to $1219. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) ticket fares go up or down.
*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
The cheapest month to fly from ORD to CYS is March when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
Enter ORD to CYS and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
United is one of the cheapest airlines offering connecting flights from Chicago, IL (ORD) to Cheyenne, WY (CYS) with a layover in Minneapolis - St. Paul Intl. (MSP), starting from around $322. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
The earliest flight from Chicago O'Hare International Airport (ORD) to Cheyenne Regional Airport (CYS) typically departs at around 5:00 AM, operated by United. This is a seasonal service available in April and June, and an early start can help you make the most of your day in Cheyenne. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
The most popular departure times for flights from Chicago, IL (ORD) to Cheyenne, WY (CYS) are in the early morning, from 6am to 9am. About 36% of passengers prefer this time window. Many major carriers, including United Airlines and Delta Air Lines, offer flights during this window. This timing is popular because it helps you make the most of your day upon arrival.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
A flight from ORD to CYS with a layover takes around 7 hours, with the route covering approximately 875 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
Select the "Business class" and "First class" filters when looking for ORD to CYS flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.
*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Cheyenne from O'Hare Intl. (ORD)?
From O'Hare Intl. (ORD), you can fly into Cheyenne Regional (CYS) to reach Cheyenne. Some flights may connect through major hubs like George Bush Intercontinental (IAH), Minneapolis - St. Paul Intl. (MSP), Lambert-St. Louis Intl. (STL) before reaching Cheyenne. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) Wyoming Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Cheyenne, WY (CYS-Cheyenne Regional) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.
Travel information
Origin airport | Chicago O'Hare Intl. Airport |
|---|---|
Destination airport | Cheyenne, WY |
Distance | 874 miles away |
Airlines serving | United |
Popular airline | United |
Roundtrip price | $290 |