Cheap flights from Chicago (CHI) to Vail (EGE)

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Lowest round trip fares by airline from Chicago and Vail

Cheapest prices ($34 One Way, $68 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

Evergreen Lodge at Vail

3 out of 5
250 S Frontage Rd W, Vail, CO
The price is $129 per night from Apr 21 to Apr 22
$129
per night
Apr 21 - Apr 22
Stay at this spa hotel in Vail. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,006 reviews)
"Would prefer better breakfast selection but other wise very convenient to skiing and both villages."

Reviewed on Mar 25, 2024

Evergreen Lodge at Vail
The Sebastian - Vail

The Sebastian - Vail

3.5 out of 5
16 Vail Rd, Vail, CO
The price is $319 per night from Apr 14 to Apr 15
$319
per night
Apr 14 - Apr 15
Stay at this 3.5-star spa hotel in Vail. Enjoy 3 spa tubs, a full-service spa, and a nightclub. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (895 reviews)
"Excellent Location"

Reviewed on Feb 26, 2024

The Sebastian - Vail
Homestake Condominiums

Homestake Condominiums

3.5 out of 5
1081 Vail View Drive, Vail, CO
Stay at this ski apartment in Vail. Enjoy free WiFi, free parking, and a free ski shuttle. Popular attractions Vail Ski Resort and Vail Recreation Path are located ...
8/10 Very Good! (33 reviews)
"My favorite thing about this condo, besides the gorgeous windows, and the convenient location, was that the owners had thought of every single thing a renter could possibly need during their stay. We've stayed in dozens of rental properties all over the US, and we are accustomed to purchasing all ..."

Reviewed on Feb 21, 2019

Homestake Condominiums
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Vail

Origin
Chicago
Destination
Vail
Number of Daily Flights
50
Earliest Flight Departure Date
Apr 4
Latest Flight Departure Date
Apr 5
Popular Airlines
United Airlines

Cheap flights from Chicago to Vail

Are you ready to book your flight, but feeling nervous about paying too much if the price drops? 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 a $50 CheapCash bonus, which you can use to save on your hotel reservation.

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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

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*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.