Southwest® flights from Chicago (Midway) to Steamboat Springs from $125
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Low fares from Chicago (Midway) to Steamboat Springs
$
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 02/27/2026
One-way
Basic
From
$125
Seen: 9 hrs ago
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 02/28/2026
One-way
Basic
From
$150
Seen: 20 hrs ago
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 02/26/2026
One-way
Basic
From
$150
Seen: 21 hrs ago
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 03/12/2026
One-way
Basic
From
$150
Seen: 10 hrs ago
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 02/19/2026
One-way
Basic
From
$150
Seen: 5 hrs ago
Chicago (Midway) (MDW)to
Steamboat Springs (HDN)
Depart: 03/03/2026
One-way
Basic
From
$150
Seen: 4 hrs ago
Explore flights from Chicago (Midway) to Steamboat Springs
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
Yampa Valley Airport
Distance:
1017 miles
Route Information
20† Weekly flights
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
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 since 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. If you’re making your visit during warmer months, there’s no shortage of outdoor adventure, either. From rafting down the Yampa River to hiking up North Routt, the breathtaking natural landscape of the Yampa Valley is guaranteed to win your heart.
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 year-round fun away from the hustle and bustle of bigger ski resort towns and enjoy the peaceful atmosphere. Whether you settle in for an evening of entertainment downtown or turn in early so you can hit the trails reenergized the next day, Steamboat Springs, CO, has a laid-back approach to living that will refresh you.
Questions we hear the most
There are 20 weekly flights from Chicago (Midway) to Steamboat Springs on Southwest Airlines.
To find the lowest fares by day and time to fly Chicago (Midway) to Steamboat Springs with Southwest, check out our Low Fare Calendar.
You can rent a car at Yampa Valley Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Steamboat Springs—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Chicago (Midway)
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.