$79 Cheap Southwest Airlines flights Chicago (MDW) to Denver (DEN)

Apply the "Price (lowest to highest)" filter on Expedia to look for cheap Southwest Airlines return flights from $134 from MDW to DEN. Affordable one-way fares from $79 are also on offer.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

To find cheap Southwest Airlines fares from Midway Intl. Airport (MDW) to Denver Intl. Airport (DEN), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the overall price. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

The first Southwest Airlines flight from MDW to DEN departs at 6:00AM UTC-6, touching down at 7:55AM UTC-7. If you want to head off later in the day, the last Southwest Airlines flight leaves MDW at 9:15PM UTC-6 and lands at DEN at 11:00PM UTC-7. Flying early is generally a good idea as morning and mid-morning flights are 20% less likely to be canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.