$100 Cheap Southwest Airlines flights Chicago (MDW) to Phoenix (PHX)

Scoring cheap one-way Southwest Airlines flights from MDW to PHX from $100 on Expedia couldn't be simpler --- just filter by "Price (lowest to highest)." Or check out our affordable return fares from $177 for your next exciting getaway.**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.

Start searching one to three months before your departure to score cheap fares on Southwest Airlines flights from Midway Intl. Airport (MDW) to Sky Harbor Intl. Airport (PHX). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also cut costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Nail your timing, and you can enjoy significant savings on domestic flights.*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 earliest flight from MDW to PHX with Southwest Airlines departs at 5:20AM UTC-6. You'll touch down at 8:30AM UTC-7. The final Southwest Airlines flight of the day leaves at 9:20PM UTC-6 and arrives at 12:20AM UTC-7. With 20% fewer cancellations for departures before midday, starting your travel day early is often the best way to go.**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.