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

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Flights from Cheyenne (CYS) to Chicago (MDW)
Origin airport
Cheyenne Regional
Destination airport
Midway Intl.
Distance
883 mi

Cheyenne to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Cheyenne to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Cheyenne to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Frequently asked questions

How much is a one-way flight from Jerry Olson Field to Midway Airport?
Make your next booking with Expedia and you could get one-way Cheyenne flights to Chicago from $595. This was the best fare found for this particular journey leaving within the next three months — an United flight, jetting off from Cheyenne Regional Airport (CYS) on June 30 2024 and touching down at Chicago Airport. The price was updated on May 23 2024 and has not changed since. Can’t wait to snap up your own bargain flights? Awesome deals are only a few clicks away.
Is it cheaper to buy a plane ticket from Cheyenne Regional Airport (CYS) to Midway Intl. Airport (MDW) last minute?
Being the spontaneous type is a fantastic way to travel around, but it isn’t necessarily the smartest method to grab a bargain flight. Think about booking your CYS to Chicago Airport trip ahead of time rather than leaving it till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Leave all that spontaneity for when you’re exploring Chicago Airport!
What is the cheapest airline flying from Cheyenne Regional Airport (CYS) to Midway Airport in the next 90 days?
With fares from $595 for a flight from Cheyenne to Chicago, United is the cheapest airline found on Expedia. This deal is based on airfares found on Expedia departing within the next 90 days and was updated on May 23 2024 and has not changed since. The flight sets off from Cheyenne Regional Airport (CYS) on June 30 2024 and arrives at Midway Intl. Airport (MDW).
What airports do you fly into for Chicago from Cheyenne?
From Cheyenne, you can reach Chicago through Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT). Research which airport works best for you before making your decision. If you opt for Midway Intl. Airport (MDW), it’s about 9 mi southwest of the city center. Use the cash you save when booking your trip with Expedia to explore the city’s top attractions, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from Cheyenne Regional Airport (CYS) to MDW?
It’s a breeze to make changes to your CYS to MDW trip yourself. Access your itinerary via the Expedia Trips portal and choose “change flight.” Browse around for new flights and secure the one that works with your new plans. You’ll get an estimate of your flight change cost, if applicable. Alternatively, use our Customer Service portal to connect with our Virtual Agent and get answers to your questions.
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