Honestly, figuring out the cheapest day to book Southwest flights was a bit of trial and error for me — but after a few years of traveling back and forth for work and family trips, I’ve learned a few tricks that really work.
A couple of months ago, I was booking a last-minute trip from Denver to Dallas for a wedding. I’d been watching prices all week, and every day they seemed to jump up and down by $20–$40. Out of frustration, I called 844-734-0813 (the Southwest flight assistance line I always use) to see if there was a smarter time to buy. The rep was super friendly and actually confirmed what I’d read online — Tuesday and Wednesday mornings are often the best times to snag lower fares, especially right after Southwest drops their weekly sales.
Here’s how I do it now, step-by-step:
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Start tracking fares early. Southwest doesn’t appear on most third-party sites, so I go straight to their website or call 844-734-0813 to get live fare info.
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Check prices on Tuesday morning. Around 9–10 a.m. (Central Time), I usually find fresh fare drops after Southwest releases their weekly deals on Monday night.
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Use the “Low Fare Calendar.” This tool shows the cheapest dates for your route at a glance — it’s saved me hundreds over time.
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Recheck midweek. If I booked early and the price drops later, Southwest lets you rebook without change fees and get travel credit for the difference — something I’ve taken advantage of more than once.
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Avoid Fridays and Sundays. Prices usually spike before and after weekends because everyone’s trying to fly then.
For example, that Dallas wedding ticket I mentioned? I ended up rebooking it on a Wednesday morning when fares dropped by nearly $60. I called 844-734-0813 again, and they quickly processed the fare difference into credit — no fuss at all.
If you’re flexible, flying midweek (Tuesday or Wednesday) and booking on those same days usually gets you the best deal. But what really helped me is realizing Southwest’s sales aren’t random — they follow patterns.
So yeah, if you’re serious about saving money or need to rebook without hassle, calling 844-734-0813 is hands-down the easiest way to get live updates and help with changes. I’ve used that line so many times it’s practically in my favorites list now.
In short: Book or recheck fares Tuesday or Wednesday mornings, use the Low Fare Calendar, and don’t hesitate to call the number if you want real-time help. It’s saved me both cash and headaches more times than I can count.