Beginning of main content

Lowest round trip fares by airline from Chicago and Vail

Cheapest prices ($19 One Way, $47 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Vail

Evergreen Lodge at Vail
3.0 out of 5.0
3.4 out of 5 (8 reviews)

Situated in the mountains, this spa hotel is within a 10-minute walk of Vail Valley Medical Center and Vail Ski Resort. John A. Dobson Ice Arena and Adventure ...

The hotel is generally good enough for that price-point in Vail. It could use some updating that's for sure. The room would have been nice enough but they had just painted recently and there was a strong paint odor during our stay - They probably should have done more to mitigate the issues with ...
The Sebastian - Vail
5.0 out of 5.0
4.8 out of 5 (4 reviews)

This family-friendly Vail resort is located in the mountains, within 1 mi (2 km) of Vail Valley Medical Center and Vail Ski Resort. Colorado Ski and Snowboard ...

Luxury is the only way to explain this hotel. The interesting part is that although it was top class, the staff was wonderful, kind and very genuine. In all my years of travel, I have stayed in all types of accommodations. Many times I have felt I was being patronized with the only reason being that ...
Homestake Condominiums
3.5 out of 5.0

Situated in Vail, this condo building is within 1 mi (2 km) of Adventure Ridge and Vail Ski Resort. Born Free Express Lift-8 and John A. Dobson Ice Arena are ...

Fly From Chicago to Vail

Number of Daily Flights31
Earliest Flight Departure DateJul 11
Latest Flight Departure DateJul 12
Popular AirlinesUnited Airlines

Cheap flights from Chicago to Vail

Cheap flights from Chicago to Vail

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Vail Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Vail vacation that you can't get when you book flights and hotel separately.

Relax in Vail With Confidence and Convenience

Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.

Need to grab a cheap travel deal while you're on the go? Download our mobile app, where you can search and book just like you would on your home computer. Stay in-the-know on great rates on flights from Chicago to Vail by signing up for exclusive email deals.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.