Act Fast: Southwest Fare Sale Starting at $44 One-Way

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Via The Points Guy, you can fly between lots of US and international cities on Southwest in coach starting at $44 one-way.

I found flights from Chicago (Midway), to Washington, DC, for $44 on December 5, 2016.  These fares are valid for travel from November 30, 2016 to March 2, 2017.  However there are blackout dates around the holidays.

To get these deals, book by October 6, 2016.

Act Fast Southwest Fare Sale Starting At 44 One Way

Book Your Southwest Sale Ticket Before They Run Out!

Here are the details.  And how to search for deals from your city!

Southwest Fare Sale

Link:   Southwest Promotion

You can check The Points Guy for how to book, or find sale fares directly on the Southwest website.  But you must book by October 6, 2016 to get the cheaper fares.

These fares are good for short hops, like from Baltimore to Long Island, or longer trips, like from Akron, Ohio, to Atlanta.

And other airlines are matching some of these fares, so decide what makes sense to you.  For example, Dayton to Chicago (Midway) costs $49 one-way with Southwest.  But Dayton to Chicago (O’Hare) costs $49 one-way with United Airlines.

Remember if you book a ticket with Southwest, you can re-book your flight (or even cancel your flight!) with no penalty.  So even if you think you might use one of the fares on sale, you can book now before the promotion ends!

And the points prices for Southwest tickets are directly related to the cash price, so booking award flights with this sale will cost you fewer points, too!

If you have the Southwest Companion Pass, this makes the deal even better!  Because you can book a sale fare and travel for (almost) free with a companion on both paid and award tickets.

Southwest Tips

In addition to the savings, there are lots of other benefits to flying Southwest including:

  • Cancel Without Penalty – You can always book now and cancel later.  On award flights the points and taxes will be refunded.  And if you book a paid flight, as long as you cancel within 10 minutes before your flight, you’ll get a credit towards another Southwest flight (good for 1 year)
  • Change Without Fees – If your plans change, you can make adjustments to your flight for free.  However, if your new flight costs more, you’ll have to pay the difference.
  • 2 Checked Bags for Free – Every passenger gets 2 free checked bags.  This saves you ~$25 per bag.
  • Bring Someone Along for the Ride for Free – With the Southwest Companion Pass, a friend or family member flies with you for free for up to 2 years!  This is an amazing deal and it’s the reason why Emily and I fly Southwest almost exclusively on domestic flights.  You can earn the Companion Pass in 8 easy steps!

Hotel Information

If you book a sale flight, remember there are lots of ways to get cheap or free hotel rooms with points from credit card bonuses and spending.

To find hotels that can be booked with points, I use Hotel Hustle (which even shows you if rooms are actually available!) or AwardMapper.

Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.  

Note:  If you prefer to book paid stays, check out discount sites like Orbitz, Expedia, or TravelPony for deals.  But remember you won’t get stay credits or points (and might not have your elite status recognized!).

Airbnb is another terrific way to save money on accommodations, especially for longer stays.  Here are some tips on how to negotiate a better Airbnb price, and how to find a safe and comfortable Airbnb.

Use a Credit Card That Earns Bonus Miles & Points

These cards earn bonus miles or points for paid airfare:

Card NameWhat It Earns
The Business Gold Rewards Card from American Express OPEN- Earn 3X American Express Membership Rewards points on airfare purchased directly from airlines when you choose this as your 3X category (otherwise earn 2X points)

- Here's my review of the card

Premier Rewards Gold Card from American Express
- Earn 3X American Express Membership Rewards points for airfare purchased directly from airlines

- $100 Airline fee credit. Up to $100 a year for incidental fees with your selected airline

- Here's my review of the card
SimplyCash® Plus Business Credit Card from American Express
- 3% cash back on airfare purchased directly from airlines when you choose this as your 3% cash back category

- Here's my review of the card
The Platinum Card® from American Express
- Earn 5X American Express Membership Rewards points for flights booked directly with airlines or with American Express Travel

- $200 Airline Fee Credit. Up to $200 a year in baggage fees and more at 1 airline

- Here's my review of the card
Barclaycard Arrival Plus™ World Elite MasterCard®

- Earn 2 miles per $1 on all purchases

- Use miles for travel statement credits (minimum 10,000 miles for $100)

- Here's my review of the card
Chase Sapphire Reserve
- Earn 3 miles per $1 on travel and dining

- $300 statement credit for travel purchases per calendar year (including hotels, airfare, etc.)

- Here's my review of the card
Chase Sapphire Preferred® Card
- Earn 2X Chase Ultimate Rewards points on travel, including airfare

- Here's my review of the card
Citi Prestige® Card - Earn 3X ThankYou points for airfare & hotels

- $250 statement credit for airfare & baggage fees each calendar year

- Here's my review of the card
Ink Business Preferred℠ Credit Card
InkBusinessPreferred
- Earn 3X Chase Ultimate Rewards points on the first $150,000 spent on travel, including airfare each year

- Here's my review of the card
Citi ThankYou® Premier Card- Earn 3X ThankYou points for travel, including airfare

- Here's my review of the card
Or pay with an airline credit card for specific perks!

And if you book a hotel, don’t forget to use one of these cards:

Card NameWhat It Earns
SimplyCash® Plus Business Credit Card from American Express
- 3% cash back on hotel rooms purchased directly from hotels when you choose this as your 3% cash back category

- Here's my review of the card
Barclaycard Arrival Plus™ World Elite MasterCard®

- Earn 2 miles per $1 on all purchases

- Use miles for travel statement credits (minimum 10,000 miles for $100)

- Here's my review of the card
Chase Sapphire Reserve- Earn 3 miles per $1 on travel and dining

- $300 statement credit for travel purchases per calendar year (including hotels, airfare, etc.)

- Here's my review of the card
Chase Sapphire Preferred® Card
- Earn 2X Chase Ultimate Rewards points on travel, including hotels

- Here's my review of the card
Citi Prestige® Card - Earn 3X ThankYou points for airfare & hotels

- Extend your trip with a complimentary 4th night stay at any hotel of your choice

- Here's my review of the card
Ink Business Preferred℠ Credit Card
InkBusinessPreferred
- Earn 3X Chase Ultimate Rewards points on the first $150,000 spent on travel, including airfare & hotels each year

- Here's my review of the card
Citi ThankYou® Premier Card- Earn 3X ThankYou points for travel, including hotels

- Here's my review of the card
Or pay with a hotel credit card for specific perks!

Let me know if you find a good deal!

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Editorial Disclaimer: Neither the responses below nor the editorial content on this page are provided or commissioned by the bank advertisers, and have not been reviewed, approved or otherwise endorsed by the bank advertisers. Opinions expressed here are the author’s alone, not those of the bank advertisers. It is not the bank advertisers’ responsibility to ensure all posts and/or questions are answered.

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3 responses to “Act Fast: Southwest Fare Sale Starting at $44 One-Way

  1. I really like the reminder of what cards to use for hotels and flights at the bottom. Thank you. I have the ink plus and I didn’t realize that’s the one I should be using for hotels for 2x.

  2. I agree, love the reminder!

    Is it possible to expand the page to show similar info adding other categories: i.e. drugstore, gas, groceries, department store, dining…..?