It’s always nice to escape Chicago in the middle of the winter. This year we’re going to visit my wife, Annie’s best friend Melissa and her family in Southern California. We haven’t seen Melissa and her husband, Scott since our wedding in 2015. So we’re going out there for 4 nights to visit with them, see their newborn baby and enjoy some nice weather.

In This Post

Airfare
Hotel
Rental Car
Bottom Line

Airfare

When I started searching for airfare from Chicago to Southern California, I knew that unless the ticket cost was astronomically high, I wasn’t going to use any points or miles. Of course I still wanted to do this as economically as possible. Melissa and her family live closest to Orange County John Wayne (SNA) Airport, but I also searched for flights to Los Angeles International (LAX), Long Beach (LGB) and Hollywood Burbank (BUR) airports.

The only viable options were LAX and SNA and LAX did have cheaper flights. However, with L.A. traffic the way it is, it was worth a little extra money to fly into SNA and avoid a 1 -2 hour drive to Melissa.

American Airlines 737-800 Aircraft — I saved $250 on airfare thanks to my Hilton Honors Aspire Card!

Flights on American Airlines turned out to be the cheapest and I was able to reduce the total cost by utilizing a perk from my Hilton Honors Aspire Card. The card comes with an annual $250 airline fee credit to use this on things like baggage or flight change fees. But what’s especially great about the perk is that American Airlines will reimburse gift card purchases and those gift cards never expire. So right after I got the Aspire Card last year, I bought $250 worth of gift cards, which were reimbursed, and now applied to the cost of this trip!

Pro Tip: As of early 2019, the gift card reimbursement still works for American Airlines, Delta and Southwest. The maximum gift card amount that will be reimbursed by American and Southwest is $100 and Delta is $50. If you purchase gift cards, make sure you buy in these smaller amounts.

After applying the gift cards, the total cost of airfare dropped from $754.80 to $504.80.

Hotel

Even though Melissa lives in Irvine, we decided to stay in Newport Beach to be closer to the ocean. The Balboa Bay Resort came highly recommended and looks very nice, but it was a little more than we wanted to pay. We finally narrowed it down to a couple Marriott hotels and one by Hyatt.

We decided on the Newport Beach Marriott Hotel and Spa. It looks really nice and got good reviews online. The real decision was how to book. I used Hotels.com to do my original search but often times you can get better rates direct from the hotel. So I went over to Marriott’s website to check the rates and they were essentially the same as what I found on Hotels.com.

I don’t currently have many Marriott points, so earning more from this stay wasn’t a great value. I’m a member of the Hotels.com Rewards program, however, and only need 3 more nights to earn a free night. This worked out perfectly since we’re staying 3 nights in total. So I booked the hotel through Hotels.com for 3 nights at $597.46. Once our stay is complete, we’ll have a free night to use on any future stay booked through Hotels.com.

To further boost my rewards, instead of booking directly at Hotels.com, I first went to MyPoints.com. MyPoints is similar to other shopping portals which give you points or miles if you start your purchase from their website. MyPoints is unique in that they have even more ways to earn points, like doing surveys or watching videos.

When I booked, MyPoints.com was giving 5 points per every $1 spent at Hotels.com. So when we complete our stay, my account will be credited with 2,635 points. Once you have enough points, they can be redeemed for gift cards to many different merchants. From a travel perspective, you can redeem for gift cards from American Airlines, Delta Airlines, Hotels.com, and Southwest Airlines. You can also redeem for miles in United’s MileagePlus program. When ready, my plan is to redeem for United miles.

For the final night of the trip, I booked us at the Embassy Suites Irvine Orange County Airport. I wanted to move to another hotel for the final night for two reasons.

I only need 3 nights at Hotels.com to earn a free future night. With the Hotels.com Rewards program, for every 10 nights you book, you earn a free night (the value of your free night will be the average price of the previous 10 nights you collect). Staying for a 4th night would give me 1 out of 10 nights towards my next free night. Since I don’t plan to use Hotels.com that much in 2019, I didn’t want to start down that path knowing I might not complete 9 more nights in a year.
The other reason is that I’m all about Hilton right now. Annie and I are collecting Hilton Honors points for a 5th wedding anniversary trip to Hawaii in 2020. Plus with my Hilton Honors Aspire Card, I earn 34 points per $1 spent at Hilton Hotels. I didn’t book all 4 nights here because we wanted to be closer to the ocean for the majority of the trip. There weren’t many options under the Hilton brand that were in the right location or budget.

Car Rental

For a car, I found a great rate through Hertz. I wanted to use Hertz because I’m planning to use them for a free rental during the Hawaii 2020 trip. And every reservation gets me points towards that goal.

At first Hertz was much higher than some others and so I had a reservation held for me through Costco Travel. A few days ago I checked Hertz again and the rates had dropped to the point where it was actually cheaper the Costco reservation.

Same as with the hotel, instead of booking directly at Hertz, I first went to the MyPoints.com shopping portal. MyPoints.com was giving 3 points per every $1 spent at Hertz when I booked. So when the reservation is complete, my account will be credited with 339 points.

Bottom Line

I didn’t use points or miles for this trip, but I did save a little money. The airfare credits from my Hilton Honors Aspire Card saved me $250 on the airfare.

Mostly, this trip will set me up for future points and miles redemptions. After this trip, I’ll have earned a free night through Hotels.com, a few thousand points to my Hilton account and some points to Hertz as well.