Annie and I have always wanted to visit Nashville together. She went years ago with a friend, but I’ve never had the chance to go. Exploring U.S. cities and immersing ourselves in their local flavors, entertainment, and vibrant culture is something we truly enjoy. Nashville, with its rich musical history and lively atmosphere, feels like the perfect destination. Recently, inspiration struck, and we decided to turn our excitement into action — planning a weekend getaway to the iconic “Music City” this June.

Using a combination of travel credits, points and miles, and a Hilton free night award certificate, I managed to book the entire trip for under $60.

Airfare

Chicago to Nashville

Earlier this year, Annie and I flew to Phoenix on United Airlines. After the original booking, the cost of the flight kept dropping. With most U.S. airlines, canceling a flight typically results in receiving the original cost as a travel credit for future use. So whenever I saw a cheaper fare, I cancelled and rebooked the flight. As a result, we had over $192 in travel credits to use on future travel on United Airlines.

Booking

We wanted to fly out on a Friday afternoon and I found two one-way tickets in economy for $350. After applying our existing travel credit to the total, I only paid $158 out of pocket. That was in mid-April.

Re-booking

In early May, I found the exact same flight for only $319. So I cancelled the original booking, rebooked at the new lower price and received the difference as a new travel credit. Finally at the end of May, I noticed that the price of the flight dropped again. This time all the way down to $205. So I cancelled and rebooked once more, ending up with an even bigger travel credit.

Pro Tip: You can cancel your paid flight with United Airlines and receive a travel credit for a future trip. So I make it a routine to periodically check prices to find a better deal. After two cancellations and re-bookings, the cost of the flight went from $350 to $205.

In the end, I was able to get the total cost of this flight down to $47! We began this whole thing with $192 in travel credits and we’re leaving with $145.

Nashville to Chicago

For the flight home, I decided to save some money and book with American Airlines miles.

Booking

The cash price for two tickets was $297, but instead I redeemed 27,000 miles. That comes out to a value of 1.1 cents per mile, which is well below the redemption average of 1.4 cents per mile. While it may not have been the most efficient use of miles, we still preferred it over paying cash. Of course, whenever you redeem miles on a domestic flight, the airlines still charge nominal fees. So in total, the cash cost for the flight from Nashville to Chicago was $11.

Re-booking

Pro Tip: Just like with the outbound flight, our inbound flight kept dropping in price. In this case the cost was decreasing in miles. After changing the flight twice, I managed to lower the total cost to just 20,000 miles.

I originally booked the flight for 27,000 miles, then 25,000 and finally 20,000 miles. Booking at 20,000 miles also increased the value of the miles redemption to a more respectable 1.48 cents per mile.

Hotel

Hilton Nashville Downtown

For hotel choices, I planned to use my Hilton free night award, which expires in August. This is a benefit I receive from owning the Hilton Honors American Express Aspire® Card. Every card-opening anniversary, I receive a free night award certificate, valid at virtually any Hilton property worldwide. Plus, I also had tons of Hilton Honors points I could redeem for the second night.

A quick search of Hilton properties in downtown Nashville, uncovered two solid options. There was the Hilton Nashville Downtown, which is located in the heart of downtown and the and the Embassy Suites Nashville Downtown. To me, the decision to choose the former was easy. The downtown Hilton property is centrally located, near Broadway and the Country Music Hall of Fame. It also has a more traditional hotel setup with upscale amenities, multiple restaurants, and a stylish atmosphere.

If I paid cash for both nights, the total would’ve been $1,078. From a points perspective, Hilton was asking for 85,000 points per night.

To use a free night award certificate with Hilton, you have to call them to book it. I provided the agent with my award certificate number, the stay dates, and my request to use points for the other night.

Note: When you use a free night award certificate, it’ll appear on the reservation like you used points for that night. For whatever reason, Hilton’s system doesn’t show that correctly. So in the screen shot above, it says I redeemed 170,000 points, but I actually only redeemed 85,000. If you’re nervous about this, you can always review your Hilton account activity to confirm the correct amount of points were deducted.

In total, I booked our 2-night stay using my free night award certificate and 85,000 Hilton points. That saved me $1,078 and we get to stay in the perfect location in the heart of downtown Nashville.

Nashville 2025 Redemption Table

	Retail Cost	Our Cost	Miles and Points Used	Points Source
2 one-way tickets from Chicago (ORD) to Nashville (BNA)	$102.50 per person ($205 total)	$47	$158 United travel credit	- Travel credit earned from rebooking prior trip for less money
2 one-way tickets from Nashville (BNA) to Chicago (ORD)	$149 per person ($297 total)	$5.60 taxes and fees ($11 total)	20,000 AA miles	- Citi AAdvantage credit cards - AAdvantage eShopping - Simply Miles
2 nights at Hilton Nashville Downtown	$539 per night + taxes ($1,078 total)	$0	1 free night certificate and 85,000 Hilton points	- Amex Hilton Aspire card
Total	$1,580	$58	- $158 United travel credit - 20,000 AA miles - 1 free night certificate - 85,000 Hilton points	- $1,522 in total savings - 96% off retail cost

Bottom Line

All in all, I saved a whopping 96% off the retail cost of this trip by using points, miles and credit card perks. Annie and I are really looking forward to immersing ourselves in Nashville’s music scene, indulging in amazing cuisine, and exploring iconic attractions like the Country Music Hall of Fame and Ryman Theater.

Trip Report Index

1. Using Points and Miles to get to Nasvhille
2. Flight from Chicago to Nashville
3. Hilton Nashville Downtown