Last-Minute Kentucky Derby Trip for Only $39!

Credit Cards, Flights, Hotels, Recommendations, Rental Cars, Travel Tools, Trip Reports / Monday, May 6th, 2019

The Kentucky Derby is a bucket list item for many. Here’s how we booked last minute flights, hotels, and transport, for less than $40 total!

Kentucky Derby Married With Miles The Gates at Churchill Downs
The Main Entrance at Churchill Downs! What a Day!

We booked this trip about two weeks ahead of time after tracking prices and options for about a week. We actually had the Derby booked last year but folded it to fly around the world.


For the flight out on Friday, we flew FREE on Allegiant Airlines using a travel credit that came with our US Bank Altitude Reserve credit card.  The airfare and upgraded seats were automatically reimbursed when the charge posted. (We could have also used the credits from our Chase Sapphire Reserve card our our Citi Prestige card.)

For our return flight on Sunday, the flights were quite expensive. We had to fly out of Cincinnati, which is a 1.5 hr drive away … at 6am. The additional miles for first class were worth around $100 per person. Considering how tired we would be, we treated ourselves.

The total cost was 34,500 miles per person plus a $5.60 fee, which we got back as part of the Travel Credit on the American Express Platinum Card!

Kentucky Derby Married With Miles Delta Air Lines First Class CVG Cincinnati Airport
We paid nothing out-of-pocket for Delta Air Lines First Class!
Kentucky Derby Married With Miles American Express Platinum Fee Reibursement Delta Air Lines First Class
The taxes were reimbursed with our Amex Platinum Card!


A week before the race, most hotel rates were through the roof. Average prices were in the upwards of $500 per night for a basic room. Award availability (aka using points) was also limited but we found the Hilton Garden Inn at the Mall of St. Matthews. For 50,000 points (worth about $250) we avoided paying the $682 cash rate.

Kentucky Derby Married With Miles Hilton Garden Inn Mall of St Matthews Cash Rate
Prices for hotel rooms were in the $500-$600’s!
Kentucky Derby Married With Miles Hilton Garden Inn Mall of St Matthews Points Rate
We were able to save $682 using points!

Any time you can redeem Hilton points for a rate of more than 1.0 cents per point is a great deal.

The same hotel was not available for Saturday.  We booked the Hampton Inn Louisville Airport hotel, which also cost 50,000 Hilton points.  The cash rate was $660.

Kentucky Derby Married With Miles Hampton Inn Louisville Airport Cash Rate
The cash rate for Saturday night was also quite expensive.
Kentucky Derby Married With Miles Hampton Inn Louisville Airport Points Rate
We paid ZERO at a Hampton Inn that was three miles away from the tracks!


Louisville is known for bourbon, and we planned on having a taste. Our hotels were not downtown, which meant that Uber and Lyft would be our Designated Drivers. That’s were our Amex Platinum $15 credits came into play.

We’d needed a rental car. Economy cars were going in the $60’s, but AutoSlash sniped us a Full Size with Dollar for $33.56.  We were literally in eyesight of the rental counter when we booked the non-refundable rate.

On the second day, we had a free National rental laying around from their 1-2-Free promotion, which we used to book a Full Size for only $5.50 in taxes.

Kentucky Derby Married With Miles National Car Rental Free Rental
Saving over a hundred dollars on a one-way rental!

The Final Tally

  • For the airfare, we paid NOTHING for over $1200 in retail value
  • For the hotels, we paid NOTHING for $1,343 in retail value.
  • For the rentals, we paid only $39 for $197 in value.

The total retail value of our trip – excluding race tickets – was $2,740! Sure, we used up our miles and points, but that’s over 98% off!


The best trips are the ones you take, and we’re grateful to have experienced Derby Day!  Saving all this money allowed us to experience the grandstand at the Kentucky Derby and do a tasting at Old Forrester Distillery. We will never forget taking our first steps into Churchill Downs!

Kentucky Derby Married With Miles Kissing at Churchill Downs
We waited until just days before to buy seats in the fourth row!

We hope sharing this will inspire you to pursue your dreams as well, whatever they may be!

If you want to support our blog, you can apply for the Amex Platinum card using our referral link here. Thanks!

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