When Is the Best Time to Book a Southwest Flight?

If you’re planning to travel with Southwest Airlines, timing your booking can make a huge difference in the price you pay. Known for its affordable fares, no-change-fee policy, and two free checked bags, Southwest is a favorite among U.S. travelers. But what many passengers don’t realize is that booking smartly—choosing the best time to book Southwest flights or even the cheapest day to book Southwest flights—can unlock even bigger savings.

In this guide, we’ll cover:

• The best day to book Southwest flights.
• How far in advance you should book.
• Tips on booking with points and rewards.
• Insider tricks like using the Southwest Companion Pass and Chase Ultimate Rewards.
• And finally, where to book for the most seamless experience.

Best Time to Book Southwest Flights

Unlike some airlines that drop flash sales randomly, Southwest follows a predictable schedule. The airline updates its schedule and fare calendar in blocks, meaning new dates open up only a few times each year.

The best time to book Southwest flights is as soon as the schedule opens for your desired travel period. Prices are generally lower right after new dates are released. Waiting often leads to higher fares as the travel date gets closer.

Pro Tip: Sign up for Southwest’s fare alerts or check regularly after a schedule extension, since introductory fares are often the lowest.

Also Read: Southwest Airlines Multi-City Flights

Best Day to Book Southwest Flights

If you’ve ever wondered whether there’s a best day to book Southwest flights, the answer is: yes. While flight prices fluctuate, many travelers have found that Tuesday and Wednesday are often the cheapest days to lock in a fare.

Why? Airlines tend to launch sales on Mondays, and competitors match them by Tuesday. This results in competitive fares mid-week. However, because Southwest fares don’t appear on third-party booking sites, you’ll need to check directly with Southwest—or book through a trusted partner like Affluence Travels—to snag the best deals.

Cheapest Day to Book Flights Southwest

For departures, the cheapest day to book flights Southwest often corresponds to less popular travel days. Flying on Tuesdays, Wednesdays, and Saturdays generally costs less than weekend departures or Mondays, which are popular for business travelers.

Pairing this with off-peak times—early morning or late-night flights—can help you stretch your budget further.

Also Read: Southwest Airlines Change Flights

How Far in Advance Can You Book Southwest Flights?

A common question travelers ask is: how far in advance can you book Southwest flights?

Currently, Southwest allows bookings up to 6–8 months in advance, depending on the schedule release cycle. This is shorter than many legacy airlines that release fares nearly a year ahead.

Booking early is particularly important if you’re traveling during peak holidays, spring break, or summer vacation. Since Southwest doesn’t assign seats, booking early also gives you a better shot at securing EarlyBird Check-In for better boarding positions.

Southwest Book with Points

Another advantage of flying Southwest is the ability to redeem Rapid Rewards points. You can easily Southwest book with points directly on their website, and the points required are tied to the cash fare. This means if you catch a sale, you’ll need fewer points for the same flight.

Points bookings are flexible, too—you can cancel or change without penalty, making them ideal if your travel plans aren’t set in stone.

How to Book Companion Pass on Southwest

One of Southwest’s most valuable perks is the Companion Pass, which allows a designated travel companion to fly with you for free (plus taxes and fees).

Wondering how to book a Companion Pass on Southwest?

1. Log in to your Southwest account.
2. Select your flight with points or cash.
3. Add your designated Companion during the booking process.
4. Only taxes and fees apply for your Companion’s ticket.

This perk can save thousands of dollars a year if used strategically.

Also Read: Southwest Airlines Cancellation Policy

Book Southwest Through Chase Ultimate Rewards

If you’re a Chase Sapphire Preferred® or Chase Sapphire Reserve® cardholder, you can also book Southwest through Chase Ultimate Rewards. Here’s how:

• Log in to your Chase Ultimate Rewards portal.
• Use points like cash to purchase Southwest flights.
• Sometimes, this gives you access to better redemption values than booking with Rapid Rewards directly.

This is especially useful if you have a large stash of Chase points and want to maximize flexibility.

Also Read: Book Southwest Airlines Group Flights

Book Smarter, Travel Better

Booking a Southwest flight isn’t just about picking a destination—it’s about knowing the best time to book Southwest flights, choosing the cheapest day to book Southwest flights, and maximizing your rewards through points, Companion Passes, or Chase Ultimate Rewards.

If you’re ready to plan your next trip, why juggle multiple sites and risk missing a deal? At Affluence Travels, we make booking seamless, affordable, and tailored to your needs. Whether you’re looking to fly with points or cash, we’ll help you find the best deal possible.

Book your next Southwest flight today with Affluence Travels and fly smarter, not costlier.

FAQs About Booking Southwest Flights

Q1: What is the best time to book Southwest flights for holidays?

A: As soon as the schedule opens—holiday fares go up quickly.

Q2: Is Tuesday really the best day to book Southwest flights?

A: Yes, Tuesday and Wednesday are generally cheaper due to fare sales and competitive matching.

Q3: How far in advance can you book Southwest flights?

A: Typically 6–8 months ahead, based on their schedule release.

Q4: Can I use Rapid Rewards points and still earn the Companion Pass?

A: Yes, flights booked with cash count toward the Companion Pass, but points redemptions do not.

Q5: What is the cheapest day to fly with Southwest?

A: Tuesdays, Wednesdays, and Saturdays often have lower fares than weekends.

Q6: Can I book Southwest flights through Chase Ultimate Rewards?

A: Yes, if you’re a Chase Sapphire cardholder, you can redeem points through their travel portal.

Q7: Is it cheaper to book Southwest directly or through a travel agency?

A: Southwest doesn’t list flights on OTAs, but booking with partners like Affluence Travels ensures you get the best price with extra support.