Intro to Flying Southwest as a Family

We have found Southwest Airlines to be by far the best domestic airline when it comes to flexibility and flight experience. If you know you don’t want to fly Southwest, check out our page on picking your first card for other card recommendations. Otherwise, keep reading to see why it is our top pick for domestic family travel. It helps that we have plenty of flight options out of Chicago. Southwest even serves some international destinations (we have flown them to Cancun and Jamaica) and now flies to Hawaii.

Perks of Southwest Airlines for Families

  • Each person can check 2 bags for free
  • Flights can be cancelled up until 10 minutes before departure. If you paid with Rapid Rewards points, the points are re-deposited into your account for no fee. If you paid with cash, you can get a refund of “Ticketless Travel Funds” which can be used for one year from when you purchased the ticket.
  • Drinks and snacks are served on all flights!
  • Though Southwest has open seating (no assigned seats), families with a child 6 or under always get to board early enough that you will be able to sit together.
  • The number of Rapid Rewards points needed for a ticket varies depending on the current cash price of the ticket–but if the price falls before your trip, you can get the difference returned to you as points or travel credit, depending on how you booked your ticket.
  • Flight attendants and crew are upbeat, funny, and kind. We even had a baggage handler once buy a pastry for our daughter at the airport…just because!

Southwest Companion Pass: Cut your flight costs in HALF!

One of the craziest deals in travel still is the Southwest Companion pass.

If one person earns 125,000 points in a calendar year, besides all those points you just got, you will also earn a Southwest Companion Pass. And get this:

For the rest of that calendar year and the next calendar year, you can name a person who will then fly with you anytime you fly and only pay about $5 in fees each way.

For the past 3 years, my husband and I have EACH held a companion pass….which means both of our kids have been flying for $5 each!

There are a few tricks and restrictions to earning a companion pass, so make sure you are prepared before pursuing this. The easiest way to do it is by opening a personal and business Southwest credit card from Chase. So you need something that will qualify for you for a business. But maybe you do! More info here on applying for business cards

Since earning our first companion pass in 2015, we have exclusively traveled on Southwest for domestic flights. If you are going for a companion pass via credit cards, you will be opening 2 Southwest credit cards (one business card and one personal card OR 2 business cards) and paying their annual fees upfront. As of October 2019, there are 3 personal Southwest Cards and 2 business card to choose from– but Chase only allows a person to get the bonus on 1 personal card per 24 months. Sign up bonuses are generally 40,000 points after spending $1000 in 3 months, but sometimes go up to 60,000 points. Recently they were 80,000 on one of the business cards! Annual fees range from $69 to $199 depending on the perks of the cards. For that annual fee, though, you are getting at least $900 of travel, much more if you end up with the companion pass.

If you’re interested in applying for one of these cards, we appreciate if you use our referral link, too!

If the idea of paying an annual fee upfront is too much for you to handle, I would suggest starting with cards that earn Chase Ultimate Rewards points, which can then be transferred to Southwest (or used for other purposes, too!) Check out our page on picking your first card for other card recommendations.

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