2022 was my post-pandemic return to travel, and I was able to do even more in 2023. In fact, since I began keeping track of these things five years ago, 2023 marked my second-best year of travel overall.

Since I’m all about using points and miles to travel, it’s ironic that my top trip of the year was paid for entirely in cash. The trip I’m referring to was the ten day tour of Italy with my daughter, Brynn, and her volleyball team. Everything was handled through a tour company, so I had no opportunity to use points or miles for anything.

For many of my other 2023 trips, however, I was able to redeem points and miles to save money. For hotel stays, I redeemed 4 free night award certificates and some points to get a total 7 free nights. In addition, I redeemed 129,200 points/miles for free flights. By utilizing these free night award certificates and redeeming points and miles, I saved a lot of money this past year!

I also achieved American Airlines AAdvantage® Platinum elite status in February of 2023. The main benefits of Platinum status are priority check-in and boarding, complimentary Main Cabin Extra and Preferred Seats at booking and two free checked bags. This really came in handy on the long flights to and from Italy, where Brynn and I got extra leg room in the Main Cabin Extra section.

I’m excited to keep the momentum I built in 2023 going into the new year. Of course I’m already planning a few trips as we speak, but now let’s take a look back at what I accomplished in 2023.

Credit Cards

• Credit cards opened: 2 (1 for me, 1 for Annie)
• Sign-up bonus points earned: 170,000 points
• Referral bonus points earned: 0 points
• Retention bonus points earned: 20,000 points
• Everyday spending: 219,252 points

Including Annie’s new credit card application, we still only opened two new cards this year. That’s the lowest number of new card applications we’ve made since 2020 and there were two main reasons for this.

The first is that after so many years of applying for new credit cards, I essentially own all the ones I want to own. There’s not much out there that still excites me at the moment. The second reason is that one of the new cards I opened this year is so lucrative, I’m concentrating my spending on that card instead of opening new ones.

Chase Sapphire Preferred Card

The Chase Sapphire Preferred Card has always been my #1 recommendation for someone who asks me how to begin the points and miles game. Annie opened the Chase Sapphire Preferred when it offered an enhanced 60,000 point sign-up bonus during the summer.

Chase allows people to earn new sign-up bonuses on any Sapphire card once every 48 months. Even though Annie had earned a sign-up bonus on this card in the past, it had been more than 48 months, so she was eligible for another one. The card has a $95 annual fee but it’s waived during the first year, which is another reason I love this card for beginners.

Note: Chase only allows someone to posses one Sapphire card at a time, so you have to downgrade or cancel yours before you can apply again.

The card’s highlights are that it earns 3x points on dining and online groceries and 2x points on travel. It also earns $50 in statement credits each account anniversary year for hotel stays purchased through the Chase Travel Portal.

Additionally, it comes with loads of great travel protections and primary car rental insurance. However the biggest perk is that it allows the transfer of Chase UR points to any of Chase’s 14 travel partners, where you can get enormous value!

Chase Ink Business Cash Card

The card I opened in 2023 was the no annual fee Chase Ink Business Cash Card. I’ve wanted this card for several years and applied for it back in 2020. They denied me back then because they said my business was too new. So I was definitely surprised when I was instantly approved earlier this year.

After meeting the sign-up bonus’ minimum spending requirement, I earned a whopping 90,000 Chase Ultimate Rewards (UR) points. However the biggest impact is that this card has supercharged the number of Chase UR points I earn on everyday spending.

The reason is that this card offers 5x points at office supply stores. Those stores sell gift cards from Visa and MasterCard that can be used just like credit or debit cards for future purchases. These gift cards usually have purchase fees associated with them, but stores like Staples and Office Depot/OfficeMax often run deals where you can buy them without purchase fees. Plus, often times you can actually make money on those deals.

Office Supply Store Example

For example, Office Depot/OfficeMax often has deals when you buy $300+ Visa or MasterCard gift cards, you get $15 off instantly. Even better, they give the $15 discount for every $300 spent. So, if you buy three $200 cards, that would cost $600 and they’d give you $30 off. If you pay for these with your Chase Ink Business Cash card, you’d pay $600 plus $23.85 in fees ($7.95 per card). However, you’d get back $30, meaning you’d make $6.15 in profit and earn 2,969 Chase UR points.

How I Use the Chase Ink Business Cash to Supercharge Points Earning

My daughter, Rory, attends summer overnight camp which costs thousands of dollars each year. The camp offers payment via credit card but charges an extra 3% if you choose that payment method. They don’t add fees if paying via debit card or by auto debit of a checking account. So I’ve been paying via my checking account all of these years, which earned me absolutely no points.

Now that I own the Chase Ink Business Cash card, I buy these gift cards from the office supply stores. I earn 5x Chase UR points on those purchases and then use them to pay for camp tuition. I’m also using this strategy to pay for other things where I previously had to pay via my checking account.

Since opening the Chase Ink Business Cash card, I’ve paid my electric, gas and auto insurance bills this way. Previously I was earning no points on those transactions and now I’m raking up 5x points. In total, I earned about 60,000 more Chase UR points in 2023 compared to 2022 and this new card has a lot to do with that.

Retention Bonus Points

Retention bonuses can be a great way to earn easy points and I earned one on my American Express Gold card this year. After the annual fee posted to my account, I called them to complain about some of the changes they recently made to the card and see if they’d offer me a retention bonus. In this case, they offered 20,000 American Express Membership Rewards (MR) points for spending a pretty reasonable amount of money on the card within six months.

All in all, I earned a total of 402,518 points on credit card sign-up bonuses and everyday spending! Now let’s take a closer look at each of the new cards we opened in 2023.

Trips: Flights and Hotel Stays

• Flights taken: 11 (4 business + 7 personal)
• Miles flown: 14,834
• Individual hotel stays: 11
• Total hotel nights: 22

In 2023, I took one big trip, a few mini-trips, a few work trips and a stay-cation. There were three highlights during the course of the year. The biggest trip by far was the tour of Italy in March. I also spent a few days with both of my daughters in Boston in July and then did a long weekend in Charleston in October with Annie and another couple.

	2018	2019	2020	2021	2022	2023
Miles Flown	10,034	34,791	0	1,634	11,023	13,314
Hotel Stays	7	20	0	3	7	11
Hotel Nights	13	38	0	7	19	22

When it comes to redeeming points and miles to reduce costs, the trip to Charleston was my best redemption. On airfare and lodging, I spent only $114 for a trip that would’ve cost $1,546 in cash!

Here’s a quick summary of those three highlight trips of 2023:

Italy

It was very special to share this kind of trip with Brynn and we’ll always have the memories we made together. As I mentioned, I didn’t redeem any points or miles on this trip, but it still was the highlight of the year!

We flew into Milan and spent a few nights there. During that time, we took a day trip to Lake Como, which was gorgeous. We then headed down to Florence, stopping in Cinque Terre and Pisa on the way. The scenery in Cinque Terre is blew my mind, but I found Pisa pretty trashy. Nobody would ever go to Pisa if it weren’t for the leaning tower.

In Florence, a some of the parents and I went to a Tuscan winery near San Gimignano for a cooking class and wine tasting. That excursion was definitely one of my top highlights of the entire trip. The setting was so quaint and the food and wine were excellent.

Boston

In July, Brynn had a volleyball camp at Northeastern University, where she’ll be playing volleyball for the next four years. While she was doing that, Rory and I explored the city.

We stayed 3 nights at the Hilton Boston Back Bay and had a great time together. We walked the Freedom Trail and learned about the Boston Tea Party at the Boston Tea Party Ships & Museum. The Freedom Trail was a little difficult to enjoy because we were sweating profusely due to the high temperatures. We had a lot of fun at the tea party museum, however, so I’d definitely recommend that if you haven’t been.

We also did some sightseeing on duck boat that took us through the city on land and water. But the most fun we had was on the North End Pizza and History Walking Food Tour. What could be better then learning some history and stopping for pizza along the way! The tour guide was a quintessential Bostonian and he made the tour unforgettable. We ate pizza at four different establishments, trying different styles along the way.

Charleston

In October, Annie, myself, and another couple spent a long weekend in Charleston, South Carolina. We absolutely loved this city and really enjoyed creating memories with our friends.

We chose Charleston mostly because its the setting of one of our favorite reality TV shows, Southern Charm. This guilty pleasure follows the lives of a group of Charleston singles.

During our trip, we visited many of the locations we’d seen on the show, hoping to run into a cast member of two. While extremely silly, we laughed a ton as we recounted stories from the show and made our way to the various bars and restaurants. And as luck would have it, we did run into Craig Conover at his store, Sewing Down South.

All silliness aside, Charleston has so much charm and is a go-to destination for foodies. We feasted on traditional “low country” staples like oysters, shrimp and grits, fried green tomatoes and fried chicken!

I was able to save $1,432 on airfare and hotels using points and miles. For the airfare, I redeemed United Airlines miles on the flight to Charleston and United TravelBank credits on the flight back to Chicago. The TravelBank credits were earned as a perk of owning the Hilton Honors American Express Aspire card.

For the hotels, we stayed two nights at the The Lindy Renaissance Charleston Hotel, which we just loved. It exudes southern hospitality and the location can’t be beat!

The final night, we stayed at the Courtyard by Marriott North Charleston, near the airport, because we had a really early flight the next day.

I used a free night award certificate and redeemed 55,000 Marriott points for The Lindy Renaissance and booked the Courtyard with Annie’s new Chase card via the Chase Travel Portal. The Courtyard was already pretty inexpensive, but I booked it that way to get the $50 Chase Sapphire Preferred rebate on hotel stays booked through the portal.

Points Redeemed

For the year, I redeemed 331,200 total points/miles. That broke down to 129,200 points/miles for flights and 202,000 points for hotel stays.

Airfare Redemptions

• 37,000 American Airlines miles were redeemed for airline tickets from Chicago to Portland (for a 2024 trip)
• 75,000 Chase Ultimate Rewards points were redeemed for airline tickets from Chicago to Boston
• 17,200 United Airlines miles were redeemed for airline tickets from Chicago to Charleston

Hotel Redemptions

• 140,000 Hilton points were redeemed for the hotel stay in Boston
• 55,000 Marriott Bonvoy points were redeemed for the hotel stay in Charleston
• 7,000 Marriott Bonvoy points were redeemed for the hotel stay in Indianapolis

Points Transferred

I also transferred a total of 3,000 points to Air Canada Aeroplan via Chase and American Express.

• 3,000 points went to Air Canada

Air Canada

Originally I transferred 1,000 American Express MR points to Air Canada simply to keep my Aeroplan miles from expiring. Then later in the year, Chase was running a promotion to receive 20% more miles when transferring Chase UR points to Air Canada. So I took that opportunity to transfer 2,000 Chase UR points to Air Canada to get my balance above 20,000 miles.

Points earned off airline flights and hotel stays:

• American Airlines: 17,486 miles
• United Airlines: 400 miles
• Hilton Hotels: 22,685 points
• Marriott: 26,276 points

Promotional Activity

Promotions come in many forms, but the most common is earning bonus points/miles or cash back on certain purchases. Signing up for promotions is free, so I make it a point to register for every one I come across.

Points and miles earned via promotional activity in 2023:

• American Airlines: 7,500 miles
• United Airlines: 6,168 miles
• Hilton Hotels: 13,410 points
• Marriott: 18,000 points
• American Express Membership Rewards: 5,321 points
• Citi ThankYou Rewards: 4,950 points

In total, I earned just over 55,000 bonus points/miles in 2023. Not as great as the prior year, but there’s still free, so who cares. Below you’ll find more detail on how I earned those American Express Membership Rewards points, Marriott Bonvoy points and American Airlines miles via promotions.

American Express Membership Rewards Points

American Express had a few nice promotions during the year, which they deliver via Amex Offers. One of them popped up on my American Express Gold card and offered an additional 2x points at supermarkets. That card already earns 4x points in that category, so I was able to earn 6x points until I reached the maximum allowed.

In another Amex Offer, they gave 5x points at Amazon up to 2,500 points. In total I earned 5,321 American Express MR points via promotions in 2023.

Marriott Bonvoy Points

Marriott ran a bunch of valuable promotions in 2023. In one case, they gave 1,000 bonus points plus one bonus Elite Night Credit for each night stay. Those extra elite night credits went a long way in helping me earn Marriott Bonvoy Gold Elite status for another year.

In another promotion, Marriott offered 1,500 bonus points for each hotel stay, plus an additional 3,000 bonus points for every three different brands you stay with.

Marriott always runs some pretty great promotions each year, so I make sure to register whether I have a trip scheduled or not. If I don’t register right away, I’ll probably forget. Then should a trip pop up during the promotional period, I’ll be sure to earn those valuable bonus points.

American Airlines AAdvantage Miles

On three separate occasions, my Citi credit cards offered bonus American Airlines miles, with very small spending requirements. Each time, the promotion offered 5x miles on online purchases up to a total of 2,500 miles. When promotions like these occur, I simply switch my purchases to the applicable credit card. Then once I’ve earned up to the maximum points, I just switch back to cards I typically use.

Surveys

The amount of time I spent doing surveys in 2023 fell to its lowest level ever. When I did spend time doing them, it was always because of some kind of promotion to earn extra rewards. I just don’t have the time anymore to devote to earning points and miles this way. Plus the amount of points and miles that can be earned is simply not enough to justify the time spent.

I earned points via 4 different survey websites, for a total of 18,235 points/miles. Points and miles earned via surveys in 2023:

• American Airlines: 2,144 miles
• United Airlines: 1,100 miles
• Alaska Airlines: 991 miles
• Hilton Hotels: 14,000 points

Shopping and Dining Portals

Shopping and dining portals are another easy way to earn extra points and miles.

For online shopping, instead of going directly to the merchant, start at a shopping portal first. There are tons of different shopping portals out there, so I like to check Cashback Monitor to see which ones are giving the most bonus points at that merchant. Since I was going for American Airlines elite status again, I typically used their American Airlines AAdvantage eShopping portal unless another portal was far and away the better option. In total, I was able to rack up over 38,000 American miles just from their shopping portal.

With dining portals, any restaurant participating with the Rewards Network will earn bonus points or miles. You must register your credit cards before dining, and then points/miles will accumulate automatically.

Points and miles earned via shopping and dining portals in 2023:

• American Airlines: 38,119 miles
• United Airlines: 2,725 miles
• Chase Ultimate Rewards: 2,470 points
• American Express Membership Rewards (via Rakuten): 8,444 points

Bottom Line

There was a lot going on and a lot I accomplished in 2023! I feel fortunate to have taken wonderful vacations with my daughters, with Annie and with together with friends. I not only maintained my American Airlines elite status, but I moved up from Gold to Platinum. I also earned more Chase points on everyday spending then I ever have thanks to my new Chase Ink Business Cash card!

I can’t wait to see what kind of travels I’ll do in 2024. In the meantime, I’m going to continue earning as many points and miles as possible to use on those future vacations. Happy New Year!