Our experience utilizing points for free travel - trying out hotel and airline cards

Sunset Ocean City, Md 2015

I want to start by explaining the options you have when signing up for Travel Credit Cards.  Hopefully this table will help explain your options.

Hotels	Airline Cards	General Travel/Transferable	Cash Back
Hilton	Southwest	Chase Sapphire cards	Chase Freedom
IHG (Holiday Inn)	Delta	Chase Ink Business	Fidelity Cash Back
Marriott	United	American Express Gold/Platinum	Capital One Venture
SPG	American Airlines	Citi Prestige/Preferred	American Express Everyday
Hyatt		US Bank Flexperks
Potential Benefits:	Potential Benefits:	Potential Benefits:	Potential Benefits:
Sign up bonus	Sign up bonus	Sign up bonus	Sign up bonus
Free Nights Bonus points Free breakfast	Status (early boarding,  lounge access)	Lounge Access, rental car insurance, TSA Precheck, Car rental/Hotel Status, Travel spend reimbursement	Cash back can be used for almost any charge, redeem for gift cards
	Baggage perks

There is value in every category.  If you frequent one airline or hotel chain it probably makes sense to sign up and use their credit card. 

If you want options sign up for the general travel or transferable cards.  Transferable cards mean that you can transfer the points into different frequent traveler programs.  These transferable points are usually worth more than a penny per point, you could get more than 2 cents per point transferring these points to airline/hotel loyalty accounts.  For instance I mostly transfer my points earned on Chase Cards (Chase Sapphire Reserve and Freedom) to Southwest.  These points mostly transfer 1 to 1 meaning if I transfer 10,000 Chase Ultimate Rewards points to Southwest my new SW balance will be 10,000 points greater.  10,000 SW points are worth between $120 to $180 when booking award travel on southwest.com.   To summarize the points discussion above, points are often more valuable when you transfer to loyalty accounts than when you redeem for previous travel purchases or gift cards.  

It was about two years after opening my first points credit card that I signed up for more.  I had been tired of driving to my annual guys golf trip in Myrtle Beach and wanted to start flying.  After some research I found out Delta had the best current sign up offer (this was end of 2011, early 2012).  The Delta American Express Gold Card provided 30,000 points which at the time could be used to book reward flights or reduce airfare by $.01(penny)/point or 30k=$300.  This card also comes with free baggage and some status.  The baggage perk was nice since golf bags can be expensive to check on some airlines (another reason we love Southwest – free to check golf bags).  Delta miles used to book reward flights can be very valuable.  See below – One way nonstop flights from Columbus to Cancun during winter can be booked for 15,500 points.  Just a year or so ago Kim was able to sign up for an American Express card that offered a 150,000 points bonus.  We are still waiting for a good opportunity or babysitter to use these points.    

Our next airline credit cards were through Southwest.  We both opened Chase Southwest Premier cards which got us 50k points each after a meeting the minimum spend requirements.  In my opinion Chase Southwest Cards are the best airline cards available for family travel.  We used these 100,000 points to fly to Fort Myers multiple times and took Macie to see Disney when she was 18 months old.  If you plan your trips ahead of time you can easily get non-stop roundtrip flights to Orlando from Columbus for 7,500 points per flyer and other Florida beach destinations for 15,000 points in winter.  I’m assuming most Midwest cities cost similar points.  Flights are usually cheaper if you leave and return during the week.  As our kids get older and start school this will increase the cost of flying.  Before Macie started kindergarten we mostly traveled Wednesday to Tuesday or something similar.    When booking award travel through Southwest you need to keep an eye on the Southwest schedule extension calendar.  It can be found below:

https://www.southwest.com/air/flight-schedules/index.html

Our trip to Marco Island, Florida 2015

I find the best time to book award travel is once the schedule is extended.  One of the perks of Southwest is no fee change rules.  You can always change your booked flights if the price drops.  I periodically check the price of my booked flights.  Most times I check prices when Southwest sends out a sale email blast. 

Some people might be reading this and think wow opening up all these credit cards must kill their credit score.  However, it’s done quite the opposite for us.  Opening these cards and paying off our balance each month has increased our credit score but it all depends on your individual situation.  Again we are not experts I’m just going over our past and present experiences.  You can read more about how applying for credit cards may influence your credit score here:

http://www.myfico.com/crediteducation/new-credit.aspx

I know this is a lot of information.  Please ask questions below in the comments.