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Lowest round trip fares by airline from Chicago and Vail

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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 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.

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.

Packages from Chicago to Vail

Vail vacations with economy flights

Hotels in Vail

See all 1,278 Properties in Vail
Tivoli Lodge

Tivoli Lodge

386 Hanson Ranch Rd, Vail, CO
    4.0 out of 5.0
     
     
    5.0 out of 5 (6 reviews)

    Located near the slopes, this Vail hotel is in the mountains and within a 10-minute walk of Cogswell Gallery, Vail Ski Resort, and Betty Ford Alpine Gardens. ...

    Tivoli Lodge$149

    Tivoli Lodge$149
    Grand Hyatt Vail

    Grand Hyatt Vail

    1300 Westhaven Drive, Vail, CO
      5.0 out of 5.0
       
       
      5.0 out of 5 (1 reviews)

      Located in the mountains, this slopeside hotel offers ski-in/ski-out access in Vail within 2 mi (3 km) of Adventure Ridge and Vail Ski Resort and close to winter ...

      Grand Hyatt Vail$179

      Grand Hyatt Vail$179
      Evergreen Lodge at Vail

      Evergreen Lodge at Vail

      250 S Frontage Rd W, Vail, CO
        3.0 out of 5.0
         
         
        3.4 out of 5 (8 reviews)

        Located near the slopes, this Vail hotel is in the mountains, within a 15-minute walk of Vail Valley Medical Center and Vail Ski Resort, and close to winter ...

        Evergreen Lodge at Vail$119

        Evergreen Lodge at Vail$119
        The Arrabelle at Vail Square, A RockResort

        The Arrabelle at Vail Square, A RockResort

        675 Lionshead Place, Vail, CO
          5.0 out of 5.0
           
           
          5.0 out of 5 (1 reviews)

          Located in the mountains, this ski-in/ski-out resort in Vail is within 1 mi (2 km) of Adventure Ridge and Vail Ski Resort and close to winter sports such as ...

          The Arrabelle at Vail Square, A RockResort$279

          The Arrabelle at Vail Square, A RockResort$279
          Sonnenalp

          Sonnenalp

          20 Vail Rd, Vail, CO
            5.0 out of 5.0
             
             
            5.0 out of 5 (3 reviews)

            Located near the slopes, this Vail hotel is next to a golf course, within a 10-minute walk of Vail Valley Medical Center and Vail Ski Resort, and close to winter ...

            Sonnenalp$219

            Sonnenalp$219
            Four Seasons Resort Vail

            Four Seasons Resort Vail

            1 Vail Rd, Vail, CO
              5.0 out of 5.0
               
               

              Located near the slopes, this Vail resort is within a 10-minute walk of Vail Valley Medical Center and Vail Ski Resort and close to winter sports such as cross-country ...

              Four Seasons Resort Vail$278

              Four Seasons Resort Vail$278
              Vail Marriott Mountain Resort

              Vail Marriott Mountain Resort

              715 West Lionshead Circle, Vail, CO
                4.0 out of 5.0
                 
                 
                5.0 out of 5 (1 reviews)

                Located in the mountains, this slopeside Vail resort offers ski-in/ski-out access within 2 mi (3 km) of Adventure Ridge, Vail Ski Resort, and Betty Ford Alpine ...

                Vail Marriott Mountain Resort$170

                Vail Marriott Mountain Resort$170
                The Sebastian - Vail

                The Sebastian - Vail

                16 Vail Rd, Vail, CO
                  5.0 out of 5.0
                   
                   
                  4.8 out of 5 (4 reviews)

                  Located in the mountains, this ski-in/ski-out resort in Vail is within a 10-minute walk of Vail Valley Medical Center and Vail Ski Resort and close to winter ...

                  The Sebastian - Vail$239

                  The Sebastian - Vail$239
                  The Lodge at Vail, A RockResort

                  The Lodge at Vail, A RockResort

                  174 Gore Creek Dr, Vail, CO
                    4.0 out of 5.0
                     
                     
                    2.7 out of 5 (3 reviews)

                    Located near the slopes, this Vail hotel is in the mountains, within a 5-minute walk of Cogswell Gallery and Vail Ski Resort, and close to winter sports such ...

                    The Lodge at Vail, A RockResort$169

                    The Lodge at Vail, A RockResort$169
                    DoubleTree by Hilton Vail

                    DoubleTree by Hilton Vail

                    2211 North Frontage Road, Vail, CO
                      3.5 out of 5.0
                       
                       
                      1.0 out of 5 (1 reviews)

                      Located near the slopes, this Vail hotel is 9.8 mi (15.7 km) from Vilar Performing Arts Center and close to winter activities such as cross-country skiing and ...

                      DoubleTree by Hilton Vail$130

                      DoubleTree by Hilton Vail$130
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      *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.