Flights from Chicago (MDW) to Steamboat Springs (HDN)

Trade skyscrapers for different peaks that touch the sky with a Southwest Airlines® flight from Chicago (Midway) to Steamboat Springs, CO. Find a cheap flight from Chicago Midway International Airport to Yampa Valley Regional Airport for your next Rocky Mountain adventure. If you have a wide travel window, explore our Low Fare Calendar to find the cheapest available tickets inside your travel dates. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.

Get a break from the Windy City and pack your puffer coat for a wintertime trip to Steamboat Springs, CO.

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Low fare alert

Chicago (Midway), IL to Steamboat Springs, CO

departing on 1/04

one-way starting at*

Book now

*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 41 travel days available.

Check out Chicago (Midway) to Steamboat Springs, CO, flights and book yours now!

Middle seats open through November 30

Full exchange of fresh, outdoor air every 2-3 minutes while inflight

Face coverings required

Travel Advisory

During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our Coronavirus Travel Information page for information about potential restrictions on air travel.

Flight details

Departing from: Chicago Midway International Airport (MDW)

Arriving at: Yampa Valley Regional Airport (HDN)


Explore Steamboat Springs

There’s more than skiing in Steamboat Springs, but winter sports are certainly one of the top draws to Yampa Valley. Chicagoans are no strangers to winter temperatures and plenty of snow, but skiing isn’t exactly a popular pastime—the Midwest is not known for its mountains. Skiers of all levels have plenty of options when they choose to hit the slopes. The Howelsen Hill Ski Area offers slopes rated from easy to difficult, so groups with varied abilities need not head to different destinations. Seasoned skiers looking for the ultimate challenge can find expert-rated runs at Rabbit Ears Pass Trails. Proceed with caution—you won’t want to miss the rest of your snow-bound excursion.

Living on Mountain Time is a far cry from life in the city, and that’s one reason why city folks find themselves in Steamboat Springs. Indie vibes and small-town charm meet in this Rocky Mountain town, and locals can’t wait to show you a great time with a heaping helping of their unique brand of hospitality. Pursue winter fun away from the hustle and bustle of bigger ski resorts and enjoy the peaceful atmosphere. Whether you settle in for an evening of entertainment by the fire or turn in early so you can hit the slopes reenergized the next day, Steamboat Springs, CO, has a laid-back approach to living that will refresh you.

Get ready to experience small-town life combined with all of the amenities a traveler could want. Answer the call of the bubbling hot springs and get ready to let your day-to-day worries melt away. Say goodbye to the chaos of big-city life and plan your next mountain adventure today.

Travel tips


Infancy policy

One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.


Pet policy

Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.


Unaccompanied minor

Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.


Bags fly free®1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest® travel experience

It takes more than getting a cheap flight to make traveling pleasurable. That’s why Southwest works to make every step of the process of getting to your final destination simple, from booking to boarding. Learn more about what you can expect from the Southwest® Experience before you book your next flight from Chicago Midway International Airport to Yampa Valley Regional Airport.

Get on your way to your next adventure today. Book your next flight to Steamboat Springs, CO, with confidence, knowing that you won’t have to worry about hidden fees—Southwest offers low fares and, as always, bags fly free. That’s Transfarency.® Want to stay in the know about our latest flight and vacation package deals? Enroll in our Click 'N Save® emails. For more information on tours, activities, and more hidden gems, check out Southwest Airlines® Experiences and earn Rapid Rewards®® points when you fly.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.

Questions we hear the most

What day is it cheapest to fly from Chicago (Midway) to Steamboat Springs, CO?

To find the cheapest day and time to fly Chicago (Midway) to Steamboat Springs, CO, with Southwest, check out our Low Fare Calendar.

Can I rent a car at Yampa Valley Regional Airport?

You can rent a car at Yampa Valley Regional Airport—book yours with your flight.

Can I change my flight reservation for my flight from Chicago (Midway) to Steamboat Springs, CO?

Yes! Flights from Chicago (Midway) to Steamboat Springs, CO—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.

Where can I find the status of my flight from Chicago (Midway) to Steamboat Springs, CO?

Check the status of your upcoming Southwest flight here.

Where can I find answers to other questions about flying from Chicago (Midway) to Steamboat Springs, CO, with Southwest?

Check out the Southwest Airlines® FAQs for answers about everything Southwest.