Non-Stop Flights to Ski Resorts From Chicago

While Chicago is within driving distance of a number of Midwest ski areas, it’s not considered a gateway city to ski resorts like many other U.S. metros. However, it’s easy and convenient to fly direct from Chicago to a number of ski destinations. In the time that it would take to drive to a Midwest ski resort, travelers could fly direct to some of the nation’s best ski resorts. Not to mention that travelers can avoid the stress and headaches of Chicago traffic, especially on a holiday weekend. Let us help plan your next great ski trip with our flight guide of non-stop flights to ski resorts from Chicago.

See more of our North America flight guides here.

Chicago Flight Guide

>Get to Know Chicago Airports

Chicago is home to two international airports, Chicago O’Hare International Airport (ORD), one of the busiest airports in America, and Chicago Midway International Airport (MDW). The Blue Line L train takes travelers to O’Hare, while the Orange Line L train takes travelers to Midway. However, it can often be much quicker to take a cab or rideshare, especially to O’Hare, since it’s nearly 20 miles from downtown Chicago. Midway is much closer to downtown Chicago, located 11 miles away, making it more convenient for many people.

Chicago O’Hare has several hundred flights daily, the majority of those on United. Alyeska, Aspen, Bozeman, Jackson, and Lake Tahoe are just a few of the ski destinations that United flies to. Many of the other major carriers, including American, have flights out of Chicago to ski destinations, too. Southwest is the airline that most skiers will fly on out of Midway, since Southwest flies to a few ski destinations, including Colorado.

Non-Stop Flights From Chicago

While all of this can feel a little bit like advanced calculus, we’ve made it easier for you to plan your ski trip. Below you’ll find flights from Chicago to some of the top U.S. ski destinations. Some of these flights are seasonal, while others can change without much notice. We recommend checking with the airline for specific times and availability as you plan your trip.

Know Before You Go

It’s no secret that a ski trip can often take a little bit more planning and preparation. And that’s particularly the case when flying into a smaller destination or regional airport, like many of the flights listed above. As such, we recommend booking your flights as far in advance as possible. In some cases, ski destinations may only have one flight per day, with those weekend flights filling up months in advance.  

Additionally, ground transportation and rideshare in ski towns may not have the accessibility and availability as major cities. As we mentioned above, there’s a variety of transportation options to and from Chicago’s airports. Cabs and rideshare operate out of both airports, while both airports are also served by shuttles and regional buses. While it’s always recommended to give plenty of time to arrive at the airport, this is especially the case in a major city like Chicago, where traffic can be unpredictable. 

Finally, no matter where you’re flying in and out of, we recommend giving yourself some extra time. Winter weather, traffic, and the time to check ski gear and get through security can all be unpredictable. For one less thing to think about, consider shipping your skis or snowboard.