How I Booked A Last Minute Trip With Points And Saved More Than $1200

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Yesterday, I posted on Instagram that I was going to buy same-day airline tickets to a destination based on recommendations simply to highlight the value in having points.

I mentioned that I had a few prerequisites:

  1. Big City
  2. Midwest / East Coast (preferably around some water)

Within a few seconds I received the first response, “Boston or Chicago.”

Boston is an amazing city but I hadn’t been to the city of Chicago in a long time so it really stood out. Obviously, purchasing a ticket for a flight that departs within 24 hours (or even less than 30 days), can be extraordinarily expensive so, immediately, I began thinking about possible ways to use points.

I had recently flown from California to Atlanta. Atlanta Hartsfield Airport (ATL) was the closest airport at the time so this example will focus on ATL.

One often overlooked aspect of frequent flyer programs is having the ability to use frequent flyer miles from one airline on a partner airline. For example, you can use United Airlines’ miles to fly on any partner in Star Alliance or use Delta skymiles to fly on any partner in Skyteam Alliance.

For my last minute flights, I knew the best choices would be:

  1. using points to fly on Delta Airlines or;
  2. using points to fly on American Airlines

Delta Airlines has been having frequent flash sales so I checked just to see how many miles Delta would be requiring for the redemption. I also checked for comparison. Below are the results and some quick thoughts:


  • ATL-ORD (They also fly to Chicago Midway (MDW) for the same price)
  • Costs: 25,000 miles + $5.60 one-way (so 50k roundtrip)
  • Pro: A lot of flights to choose from because ATL is a Delta hub
  • Con: 25,000 miles one-way!? #hardpass especially knowing I posted THIS just two days ago.


  • Costs: 12,500 miles + $5.60 one-way (so 25k roundtrip)
  • Pro: A lot of direct flights because ORD is an AA hub, ½ the price of Delta
  • Con: 12,500 miles is ok but not as good as it gets (details below)


Do you remember how I said you can use miles from one airline to fly on a partner airline? Well, British Airways and American Airlines are partners (both part of the oneworld alliance) which means I can use my BA miles to fly on AA planes for 7,500 miles + $5.60 (one-way). If you’re unfamiliar with this trick, READ THIS (& then THIS).

Important Note: When using miles for a partner airline award ticket, you can only book when a “saver award” is available. 99% of the time there is saver availability in economy however premium cabins (e.g. business and first class) are not always available.

You may be saying “…but I’ve never flown on British Airways, let alone, have any British Airways miles.” No worries at all… this is where transferrable points (also known as having the right credit card) become a game-changer. You can instantly create British Airway miles with the following credit cards…


We’re traveling as a family so I decided to pick a hotel in the loop (downtown Chicago). The convenience of having EVERYTHING within walking distance is worth the premium. Fortunately, I have a “free night certificate” for a Marriott hotel and quite a few Marriott points so I focused on Marriott properties.

Traveling with an infant can be challenging so I chose a hotel (review coming soon) that has complimentary breakfast. The convenience of having free breakfast downstairs is important. I also enjoy trying brands that I’ve never stayed in so this will be fun.


As you may know by now, I’m an aviation geek. I love everything about planes…flying in the front, flying in the back, watching them take off and arrive, trying to identify them from far away, etc. Well, ironically, the Chicago Air Show is taking place this weekend and it’s something that I’ve always wanted to attend so this is turning out to be an outstanding redemption in terms of heartfelt joy alone.

Normally, the details of my trips are planned in advance. But, again, I have done all of this to show how having points can allow you to do things when cash rates would otherwise would be restrictive.

I can’t stress enough the importance of diversifying your credit cards and points holdings across the various major reward programs. Having the flexibility to utilize my BA Avios points instead AA points (TO FLY ON THE SAME EXACT PLANE), saved me 10,000 points on the flight alone! Additionally, we had the option to stay at hotels ranging between Hyatt, Marriott, and more.


  • Flights: ATL-ORD $412 (per person, roundtrip)
  • Train: ORD – Downtown Chicago: $20 ($10 per person, round-trip)
  • Hotel – 1st night: $188 (excluding taxes)
  • Hotel – 2nd night: $249 (excluding taxes) probably high because of the airshow
  • Total = at least $1281


  • Flights: ATL-ORD (round-trip)
  • 15,000 miles + $11.20 (me)
  • 15,000 miles + $11.20 (wife)
  • 1500 miles (daughter – $0 for infant in arms)
  • Train: ORD – Downtown Chicago: $20 ($10 per person, round-trip)
  • Hotel – 1st night: Redeemed free night certificate that I receive just for having the credit card
  • Hotel – 2nd night: redeemed 35,000 Marriott Points
  • Total = $42.40

Savings = $1238.60

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