Traveling to San Francisco with a Toddler

CLEveland to SanFranciscO for Free Using United Points

A couple of years ago, planning a trip anywhere in the world for us was fairly easy.  Now however, we have a 1.5 year old with us, and he’s not too fond of 12 hour drives in the car or long layovers.  We waited 2 years to take our son Leo on his first flight, but you can fly with a child older than 2 weeks without any issues on every US airline.  They also give you an option to ‘Lap-Sit‘ your child, which means you pay only 10% (or nothing) the cost of your ticket for the ‘Infant Ticket’.  The catch is they have to sit on your lap the entire time.  After two they HAVE to buy their own seat.


Our family has been jonesing for a cross-coastal trip for a while now, and we think Leo is ready for his first plane ride.  My brother lives in San Francisco, so we didn’t really need a hotel… However, we did want the quickest (IE Non-stop) flights from CLE to SFO, and we’d also like to visit Monterrey Bay while we’re staying there.  That city 2 hours or so south of San Fran has an amazing Aquarium, places to kayak and hike, and plenty of places to see Sea Lions up close in their natural habitat.

Even though we could probably spend a day there and leave late at night, I thought it would be more fun to splurge on a fancy hotel.*

Hotel Portion

*For this weekend evening, we utilized BOTH of our IHG FREE NIGHT Certificates.  My opinion is that those ‘Good ANYWHERE’ Certs are best used at the most expensive place you can find… and at a supposed $949 a night, i think we did well.  Only an insane person would spend that on ONE room, and that option doesn’t even guarantee an ocean view.  We used two certs because they only allow 3 people in a room, and we didn’t want to subject the newlyweds to the incessant midnight cries of a toddler.  Although it would be a nice sneak preview of whats to come  =)

The hotel is beautiful, and located in the heart of Monterrey Bay, along the coastline.

We booked about  9 months in advance and there were plenty of options… We needed two rooms, so I choose that when selecting the dates / ‘Pay with Points’ option.  Then we individually applied each of our certificates to the same night.  We then called the desk and told them we wanted to add my brother to one of the rooms, and viola‘.  It should be noted that while they do have suites and oceanview rooms, you will not get these with the Free Night cert, because they love m oney and you’re paying them $49 for this room (via your annual CC fee.)

The hardest part of this trip will be fitting 4.5 people into a Fiat.

Free Flights

The Flight portion of this was the most difficult, since United puts you at their mercy with Blackout Dates.

But they claim not to have black out dates!?” – That is correct.  Instead of ‘blacking a date out‘ – they simply make it available at 2-4x the usual price, making you a fool to waste your points unless you need that particular  flight desperately.

Only Frontier and United fly Non-stop CLE-SFO, and that was a requirement for our first light to make it as easy as possible for a toddler.  This also meant only having 2 flights to choose from, the daily runs that United Offered.  Frontier also offers a credit card that will give you 2 free flights, which we will utilize once we’re way past 5-24.

These tickets were in the ballpark of $400 EACH so at 1.6 cents per point, we did pretty well.  (75,000/$1,200 – That’s the average SW Price as well, United’s average is between 1 and 2 cents per point redemption.)  We redeemed 75,000 Chase UR Points for this flight for 3, which saved us $1,200 and cost us the effort of the  ‘Chase Ink‘ sign up.

Alternatively, we could have purchased the tickets with points at a discount on the UR Portal since we still have the CSR.  OR used our $300 CSR Travel Credit to buy tickets from Frontier Air directly.

Tickets are in the ballpark of $300 each for NON Stops, but they charge you for luggage ($75) and more.  I would not get their card until you are over 5-24 and don’t want any of the fancy Chase Cards.  $69 AF gets you 2 Free RT Flights anywhere they fly. You’re better off with a different Barclay Card, Arrival+ – which you can use for flights ANY Time, ANY Where – with NO fee.

Southwest was in the $340s and so was Delta for a 7-9 hour flight with one stop. How much is your time worth?  In my situation, we wanted to get there quickly as possible for my 2 year old son’s first plane ride, so the difference in points was worth it.


More Info:

Intercontinental on Cannery Row:   Things to do in Monterrey

750 Cannery Row : Monterrey , California ,93940, United States : +1-831-3754500


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