Is it time to convert Discover Cash Back to miles?

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If you have a stash of Discover Cash Back, but you’d rather have Southwest Rapid Rewards points or JetBlue TrueBlue points, then now may be the time to convert Discover Cash Back to miles.

convert Discover Cash Back to miles

This opportunity is contingent upon two overlapping deals:

  • Redeem Discover Cash for 1800Flowers gift certificates. $20 in Discover Cash Back gives you a $30 gift certificate. (this is an ongoing offer)
  • Earn 1750 JetBlue or Southwest points per order at 1800Flowers through 2/15/16 (JetBlue details here, Southwest details here)

I wrote about this idea before (see: How to convert Discover Cashback into airline miles), but at the time I wrote it there were no 1750 points per order deals available.  1750 points per order is the best 1800Flowers offer I’ve seen.  It seems to appear once or twice per year.  Since the offer requires a purchase of $29.99 or more, you can earn up to 58.33 points per dollar!  When you factor in the gift card discount, you’ll earn up to 87.5 points per dollar!

Overall, this opportunity makes it possible to convert Discover Cash Back to Airline miles at a rate of 1.14 to 1 (1.14 Discover cents converts to 1 airline mile).  That’s pretty close to 1 to 1.  So, should you do it?  First I’ll present the details of how to do it, then see the section titled “Should you do it?” near the end for an analysis.

Preparing to convert Discover Cash Back to miles: Join Celebrations Passport and Celebrations Rewards

STOP HERE: Joining Celebrations Passport is only worth doing if you plan to place multiple orders through 1800Flowers over the next 12 months.

For the following steps to work, you should first subscribe to the 1-800-Flowers Celebrations Passport program.  For $29.99, this service offers free shipping and handling for a year for any purchases made at 1-800-Flowers or its affiliated stores (1-800-Baskets, Cheryls, The Popcorn Factory, Wolfram’s, Harry & David, etc.).  Through 2/12 they’re also offering a $25 Restaurant.com certificate, which is arguably worth a few dollars.

Unfortunately, 1800Flowers gift certificates cannot be used to pay for Celebrations Passport (at least, it didn’t work when I last tried it).  So, you’ll have to pay with a credit card instead.

You can get a nice rebate for the purchase of this service by clicking through from a portal first.  For example, both EBates and Top Cash Back are currently offering 20% cash back for 1800Flowers (these are referral links, FYI).  Even better (if you are enrolled in Discover’s Double Cash Back for a year offer), Discover Deals is offering 20% back at 1800Baskets (which sells the same passport program).  You can find current best portal options here and here.

If you use an Amex credit card enrolled in the targeted Spend $50, get $15 back 1800Flowers offer, you’ll be $29.99 closer to reaching the $50 threshold.  And, you can use an Amex Business card to earn 5% back through OPEN Savings.  Alternatively, if you pay with a Visa or MasterCard linked to your Sears’ Shop Your Way Rewards account, you should get 20% back in SYW points.

You’ll also want to join the 1-800-Flowers Celebration Rewards program.  The program is free to join and it gives you a $20 Savings Pass for every $200 spent with 1-800-Flowers.

Once you’ve joined Celebration Rewards and you have the Passport membership in-hand, you can proceed to the following step by step approach to converting Discover Cashback to miles…

Step 1: Convert Discover Cashback to 1-800-Flowers gift certificates

Log into your Discover account and redeem your Discover cash back for one or more 1800Baskets or 1800Flowers gift certificates (they’re interchangeable).  I recommend getting one $30 gift certificate immediately prior to placing a $30 order (in Step 2).  Gift certificates are available instantly.

Discover 1800Flowers 1800Baskets

1-800-Flowers only allows you to apply one gift certificate per order online, so select a value as close to the amount you plan to spend as possible.

Step 2: Add $30 worth of stuff to your cart

Go to 1800Flowers.com and search for items that cost about $30.  Note that it is fine to click tabs for other brands such as Fannie May, Wolfram’s, and Harry & David.  I find that they often offer better products.  Fortunately, the gift cards and promo codes work for all of them as long as you start your shopping at 1800flowers or 1800baskets.

Step 3: Apply an airline promo code and pay with your Discover gift card

With either code, you’ll earn 1750 points:

  • RR82 Southwest (Note that points earned from this offer do not count towards the Southwest Companion Pass)
  • TB1750 JetBlue

Step 4: Repeat as needed

The above process converts Discover Cash Back to points in $20 increments.  If you want to convert more than $20 worth of cash, then simply repeat the above steps as needed.

Is 1.14 cents per point a good deal?

Let’s look at whether this deal is worthwhile for the airline miles alone…

By buying points in either program as described in this post, you will likely see savings if you use the points for airfare:

  • Southwest: 1750 points are worth about $26.  So, your $20 in spend can net $6 in savings (23% off).
  • JetBlue: 1750 points are worth about $25.  So, your $20 in spend can net $5 in savings (20% off).  If you choose flights at the higher end of the point value range, your savings will increase.  At the bottom end, there would be no savings at all.

Note: This analysis does not factor in the fixed one-time per year cost of joining Celebrations Passport.

Lowering the cost per mile through tax savings

It may be possible to save on taxes in a couple of ways:

  1. Individuals can use 1800Flowers to send donations to a charitable organization.  Those donations could be itemized in order to reduce your tax burden. You can find an example of how to do this in this old post.
  2. Business owners could use the 1800Flowers deliveries as business expenses.  One could send gifts to customers or employees, for example.  When treated as business expenses, these charges should reduce profits, and therefore taxes, accordingly.

I’m NOT a tax professional.  If you decide to do either, please consult your tax adviser.

Should you do it?

People often complain about 1800Flowers – for good reason.  Their products are overpriced, service is frequently poor, and the delivered goods are often not good at all.  I’ve found that you can sometimes get good stuff, though, by selecting items that are delivered by local florists, or by buying from the more specialized brands: Wolfram’s, Harry & David, etc.

Consider this if: You have a large stash of Discover Cash Back that you don’t know what to do with, and you’re likely to use miles to fly JetBlue or Southwest.

Don’t do this if: You don’t already subscribe to Celebrations Passport and you only plan to place a single order.  The cost of joining Celebrations Passport is not factored into the above analyses.  The more you buy from 1800flowers and its associated brands over the next 12 months, the more it will be worth it.

Consider this if: You fly Southwest or JetBlue regularly and often have a need for more points.

Don’t do this if: You’re willing to wait for the absolutely best deal and you don’t mind if it’s complicated. This deal gives you gift certificates for 33% off, but there are often ways to buy 1800Flowers gift certificates at half off.  In fact, right now, those who received the targeted 1800Flowers Spend $50 get $15 Amex Offer, can buy gift cards at half off by clicking through a portal offering 20% cash back and then paying for a $50 gift certificate with their Amex card.  The problem is that these cards are shipped by mail and might not arrive before the 1750 point promo codes expire.

Consider this if: You want to send multiple Valentine’s Day gifts (in $30 increments).

Don’t do this if: You don’t want to risk potential hassles.  While I’ve had no problem with this promotion this time around, I have had trouble in the past.  And, consider this recent comment from a reader (note that I haven’t had any similar issues):

Me again. THIS IS NOT WORKING:

“This deal does stack with: …
Free shipping from the Celebrations Passport program.”

I joined Celebrations Passport for $29.99 on your advice, to get free shipping for a year. However, now that the site is recognizing that I’ve joined, it DOES NOT allow for the Rapid Rewards Promo Code to be entered. It gives an error message, stating that my order is not eligible for this promotion. I called 1800Flowers and they said that others had been calling with the same issue. The woman I talked with agreed to take my order by phone and then she would submit a form to allow me to get my Rapid Rewards points (although she forgot to ask me my RR number, I had to remind her). It took a lot longer to take my order by phone that it took to enter it online. Of course I need to do this a second time now to get the next 1750 RR points and to get my AmEx amount above $50. I’ll try to do this tomorrow. But I’m now very unhappy that I paid for that Celebrations Passport because I wanted to be able to stack these deals. It is rare that I send flowers. There was no indication that I would be unable to enter Promo Codes when I joined!

If anyone has a remedy, other than calling in your order manually, please post it.

Wrap Up

I don’t fly Southwest or JetBlue often, but I certainly wouldn’t mind having a stash of points in each program.  So, I have taken advantage of the 1750 points per dollar offer in order to send Valentine’s Day and other gifts to a few people.  In my case, I had previously subscribed to Celebrations Passport, so that reduced my overall cost.  Plus, I had previously purchased a number of 1800Flowers gift certificates at less than half off (via a deal not currently available).  I did cash in $20 of Discover Cash Back for a gift certificate in order to test this deal, and that worked flawlessly… for me.

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