Deal Stacking Example – Groupon

One of the things that I’ve learned during my time in travel hacking is how to maximize every dollar I spend. In other words, I want to get the most bang for my buck. One simple way that I do this is making sure I put certain spending on cards that have category bonuses.

Another why I maximize my spending is by using a mix of portals, gift cards, and coupons. Hopefully this example will help you see a glimpse of the possibilities.

My End Goal

My wife and I visited Chicago this past weekend. Therefore, my end goal was to purchase admission (for two people) for these Chicago attractions:

  • SkyDeck Chicago
  • Architecture River Cruise
  • The Field Museum
Initial Options

As stated above, I could go through and purchase individual passes to the following attractions. Here are the following costs (for two people): SkyDeck Chicago – $44, Architecture River Cruise – $82, Field Museum – $58. Total cost would be: $58. If I went this route, I would probably use my Citi TY Premier credit card, which gives 2 Thank You Points for every $1 spent on entertainment. I’m not sure all of these attractions would code as entertainment, but it would be worth a shot. Either way I will use $184 and 368 points as my base level.


The next search I did was to look for a “Chicago City Pass” that would allow us to see the selected attractions for a packaged deal. I found a couple of options:

It didn’t take long for me to rule out the Chicago CityPass since it did not include the Architecture River Cruise that we really wanted to go on. We utilized the Explorer Pass program during our time in New York and saved a lot of money. I did a quick search and found a Chicago Explorer Pass (4 attractions) for $145 total. I would have purchased this, but we weren’t sure we’d have time to go to 4 different attractions. Because of this, I ended up searching Groupon, which is where the deal stacking comes into play.

The Groupon Example


My end goal was to purchase two of these Three-Attraction Chicago Explorer Passes for Adults for a total of $129. From previous experience, I know that I can earn miles and cashback from portals even when using a Groupon gift card.

Purchasing Groupon Gift Card (Step 1)

PPDGgrouponStep 1a: eBay Sale

Now it so happened that eBay was having a sale on $100 Groupon gift cards. I essentially saved $5.

Step 1b: Portal for eBay Purchase

Before buying the gift card, I clicked through the United MileagePlus portal, which offers me 1 United mile/$1 spent on eBay. There was also a “Fall Fun & Sports” bonus going on that if you used the United portal and spent $350 you’d get 1,000 bonus miles. I’d purchased some other deals before this so this purchase put me over the $350 mark. Because of this purchase, I earned 1,095 United miles.


Step 1c: eBay Bonus Bucks

I’ve talked about eBay Bucks before (Q1 and Q2). I purchased this gift card during a 6% Bonus Bucks promo. This gave me $5.70 of eBay Bucks.

Step 1d: Ink+ 5x UR

One thing worth knowing about PayPal digital gifts is that it codes as an Office Supply Store, which means if you have the Chase Ink+ card you’ll get 5 UR points/$1 spent. This means I’ll earn 475 Ultimate Rewards.

Purchasing Actual Groupon (Step 2)

Step 2a: Look for Promo Codes

You can look to see if Groupon has any promo codes that work on your order. This could save you roughly 15-20% sometimes. I wasn’t able to find any that worked on my order.

Step 2b: Use Portal for Groupon PurchaseCashbackMonitorGroupon

If you were able to find a promo code, it may negate portal earnings. I use Cashback Monitor to look at all the portal options. SimplyBestCoupons had 10% cashback so I opted to use them. This will give me cashback of $12.90.

Step 2c: Purchase Groupon with Gift Card

The gift card covered $100 of the $129. The remainder of the purchase ($29) I charged to my American Express SPG card since there is no category bonus for spending on Groupon. This will get me 29 SPG points. There’s another way I could get a few more Ultimate Rewards, but it wasn’t worth the hassle to me.


Purchasing each attraction separately would have cost me: $184 with 368 points earned.

However, using this deal stacking technique, this was my net cost:

  • Groupon Cost     $129
  • Less: Step 1a     ($5.00)
  • Less: Step 1c     ($5.70)
  • Less: Step 2b     ($12.90)
  • Total Costs:        $105.40
  • Other Earnings: 1,095 United miles (Step 1b), 475 Ultimate Rewards (Step 1d), and 29 SPG points (Step 2c).

That’s ~$79 saved and 1,231 more miles/points earned.

Now I understand this isn’t for everyone, but keep in mind this was money I was already planning on spending. Using a combination of portals, gift cards, and credit card rewards is one of the best ways to maximize every dollar you spend.