Puerto Rico Trip Review: Day 1 & 2 Getting to Puerto Rico

This is my second post in my series on my trip to Puerto Rico with my oldest two boys. You can find the other posts here:

Puerto Rico Trip Review: Planning Our Trip

Day 1 – Saturday

Due to the timing and availability of award space to get us from Sioux Falls to Chicago our 1st day was scheduled to be a short day and didn’t start out until about 5 pm on Saturday night with our flight out of Chicago scheduled to depart a little after 2 pm the following day.

Due to a snow storm that was forecast over the next two days Delta was offering free flight changes out of Chicago on Saturday & Sunday. This was one of those rare instances where bad weather worked out to be a blessing for me! After 20 minutes on the phone with Delta we had been re-booked onto an early flight leaving at 7:15 am instead of our original 2 pm flight!! This flight was originally over $450 per ticket more expensive than our afternoon flights which is why I didn’t book it in the first place. Thanks to the weather we were able to get on this flight at no extra cost.

The Bahamas from 30000 feet

The Bahamas from 30,000 feet

After multiple flight delays we arrived in Chicago and headed out to catch our shuttle to The Four Points O’Hare. Other than the fact that it reward nights are only 3,000 points on the weekends at The Four Points, the other reason I booked this hotel for our quick overnight was due to the free shuttle service running from O’Hare every 20 minutes.

Within 5 minutes our shuttle had arrived but unfortunately about 40 other people were waiting on the same shuttle. Before we could board the shuttle was full and we were left waiting for the next shuttle.

After over an hour of waiting in 10 degree weather and multiple phone calls to the hotel the shuttle finally made it back to pick the next group up. For whatever reason the hotel was only running one of their shuttles that night and the driver was taking his sweet time. Tired and hungry we finally arrived at the hotel, ordered a pizza and called it a night.

Day 2 – Sunday

The boys enjoying our upgraded seats!

The boys enjoying our free upgraded seats!

Sunday morning we arrived at our gate with plenty of time to spare before boarding. Our first leg would take us to Atlanta where we would board our final flight to San Juan, Puerto Rico. While we waiting for boarding I took a quick look at the seating chart for our flight and noticed that there were still 4 empty seats in first class/business class. I had already declined my upgrade as Delta only allows complimentary upgrades for Gold medallions and one companion. However with so many empty seats and no line to talk to the gate agents I decided I would try my luck.

I explained to the agent that I knew this was a shot in the dark and that I understood that my medallion status only allowed for upgrades for 2 of us. I explained that I was traveling with my two boys and asked if there was any possible chance of her upgrading all three of us since there were so many empty seats. After plugging away at her keyboard in silence, for what seemed like forever, she finally looked up and let me know that she had upgraded all three of us to first class!!! Score! It just goes to show that you never know until you ask!

I do not spend the money or points for business class or first class so this was a really big deal for the boys. With a family of six this could be the one and only time they get to ride in the front! They both took full advantage getting as many snacks and pops as the flight attendants would allow.

The flight from Atlanta to San Juan was relatively uneventful but a little long. Thankfully our flights had personal entertainment centers in the seat-backs which kept the boys entertained the entire way.

Upon landing in San Juan we headed for the baggage claim when it became all to apparent that I had forgotten something very important…. As my 9-year-old started clutching his stomach and turning an eerie shade of white I realized that I had forgotten to give him the Dramamine his mom had packed for him. We attempted to make a mad dash for the bathroom but we only made it about 30 feet before he was throwing up all over the floor in the baggage claim. Poor little guy was sick as a dog.

For about 20 minutes after pouring his lunch all over the floor he decided he felt a better. We got our bags and headed out to get our rental car. Unfortunately his motion sickness came back by the time we got to our car and we spent the next 45 minutes waiting for him to feel good enough to get in the car and head to the hotel. A couple of hours after arriving we finally made it to our hotel with only one stop on the way to throw up.

Our Gold Elite In-Room Welcome Gift at the Radisson Ambassador Plaza

Our Gold Elite In-Room Welcome Gift at the Radisson Ambassador Plaza

The first two nights we stayed at the Radisson Ambassador Plaza taking advantage of the Bonus Award Night benefit provided to Club Carlson credit card members giving us a buy one get one redemption. While this hotel is getting old and is very out-dated they do a great job of taking care of their guests. Thanks to the Gold Elite status that comes with the Club Carlson Visa cards we were able to get upgraded to a nice suite, received a nice in-room welcome gift, and free breakfast among other benefits. I will provide a complete review of the hotel in separate post. But for a total of 38,000 Club Carlson points for two nights I felt it was well worth it.

After a long day of flying and the motion sickness experience we decided to just spend the evening relaxing in the hotels roof-top pool. I was a little of my game that day and completely forgot to take any pictures of the roof-top pool area but it was nice. Although I was disappointed that there was no hot tub. We turned in early that night to make sure we were all well rested in the morning for our first big day in Puerto Rico. The next day was going to be a long day touring the old Spanish forts and playing at the beach.

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3 Responses to Puerto Rico Trip Review: Day 1 & 2 Getting to Puerto Rico

  1. Pingback: Puerto Rico Trip Review: Just My Boys and I - Part 1 - Planning Our Trip The Points Traveler

  2. Paul says:

    Betcha you don’t forget the Dramamine ever again.

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