Cheap Flights from Chicago (PWK) to West Yellowstone (WYS)

Popular airlines from Chicago, IL (PWK-Chicago Executive) to West Yellowstone, MT (WYS-Yellowstone)

Frequently asked questions

How much does a flight from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS) cost?
Secure a cheap one-way flight or cheap return flight from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS) 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 Chicago Executive Airport (PWK) to Yellowstone Airport (WYS)?
Planning your trip for is a good way to save, as it's the cheapest month for flights between PWK and WYS. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest PWK to WYS flight.
How many flights per day from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS)?
You'll need to book a flight with a layover if you're traveling from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from PWK to WYS?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS)?
Book a flight from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this time 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 Chicago Executive Airport (PWK) to Yellowstone Airport (WYS) last-minute?
Last-minute fares from PWK to WYS are generally more expensive. For the best prices, start looking for flights ahead of time. That being said, if you're flexible with your travel plans, you may find a cheap fare just before your departure.
Is it cheaper to book a PWK to WYS flight and hotel package?
You can save money by securing a PWK to WYS flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your preferred flights and accommodations, consider other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Chicago Executive Airport (PWK) to Yellowstone Airport (WYS)?
If you booked your PWK to WYS flight within the last 24 hours, you may be able to cancel or modify 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, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Chicago Executive
Destination airport
Yellowstone
Distance
1174 mi

Book with confidence

Chicago to West Yellowstone Flights

The cheapest times to fly from Chicago to West Yellowstone

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

 

The best time to book a flight from Chicago to West Yellowstone

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

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 West Yellowstone in 2025. 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 Chicago to West Yellowstone 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 West Yellowstone 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.

 

Chicago to West Yellowstone Flights

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*Available to One Key members.