A Special Trip to New York City


I just got back from The Big Apple where I helped my little sister celebrate a big birthday. Here’s how we lived in style with minimal outlay of cash. You can do it too!

Enjoy the many pics!

My sister and her two gal pals flew in from Ohio. She flew for free, non-stop, using some of the miles she earned from one of many available Delta credit cards’ sign up bonuses.

My girlfriend and I flew across the country from California on the best deal in flight: Southwest’s Companion Pass. FYI: Once you qualify for Southwest’s Companion Pass your companion gets to fly with you EVERY TIME YOU FLY – whether you buy a ticket with cash or with Southwest Rapid Rewards points (aka frequent flyer miles).

We used some points earned from the Southwest credit card’s sign up bonus for one ticket. The Companion Pass picked up the other ticket. This saved us $500 each!

Read my jibber-jabber about Southwest’s Companion Pass in detail.

If you’d like to check out these and other airline credit card options and bonuses, look at “Chip’s Favorite Credit Card Offer$” at the top right side of this website.  Click the “Airline Credit Cards”. This will take you to another site where you will see many offers.  Full disclosure: I may get a commission if you apply going through my website’s link, so… Thanks! It’s the same deal for you but I get a thank you for the referral. Email me if you have any questions.

This is what a Southwest airplane looks like against Burbank’s Verdugo Mountains:

We decided to fly from the much more convenient, smaller, nearby Bob Hope airport in Burbank (BUR) instead of Los Angeles International airport (LAX). Sure, we’d have to stop in Phoenix on our way to Newark, New Jersey instead of flying non-stop from LAX. But dealing with LAX is Hell. We decided we’d rather spend an hour laying over in Phoenix than an hour in traffic driving to LAX. Not to mention much more expensive LAX parking or Uber/Lyft.

Here we are in Phoenix Sky Harbor International airport’s Tequila Tasting Lounge inside the Barrio Café, next to La Grande Orange (not to be confused with Rusty Staub). Enjoy my new shirt.

It was going to be a full flight to Newark. Thankfully I drafted well. I coaxed a tiny twenty-something girl into our middle seat under the guise of being helpful. If a grown man sat there, we’d all be miserable.

“Middle-seat drafting” may be my superpower.

The Newark airport had extra temporary restrooms in the hallways. It’s like going to the State Fair but in an airport! Good times.

Now the hotel… Turns out hotels are ridiculously expensive! Whenever I did stand-up, hotels were included. Clearly I have lost perspective.

I figured my sister might like to be in Midtown. We stayed at Hilton Garden Inn near Central Park on West 54th. Our four nights would have been $2,080.66 per room. That’s $21.67 per hour! Nah baby, nah. Who can sleep knowing that meter is running?! If I am going to pay that much for a room, I’d never want to leave it.

The Empire Steak House was a fancy name for the hotel bar. I’ll take them at their word that they served steak as well. The glass doors folded away to make it an outdoor patio bar. Pretty cool!

My sister and her husband had received sign up bonuses on a couple Hilton cards each. Between them, they had more than enough Hilton points for this trip. Hilton lets you pool points with up to 10 other family and friends. My sister was treating her gal pals, so she grabbed a few of his points and she booked it for her and her friends.

As a long time Hilton Honors hoarder, I plunked down points for our room. I also had a free weekend award from the Hilton Ascend card that I used for Saturday night.

The rooms were small but mighty. The bed was comfortable – no depressions in the mattress. This bed frame waged and won a relentless campaign against my shins.

Right now, Hilton has a couple personal credit cards. One has a 75,000 point sign up bonus and no annual fee. The Hilton Ascend card has a 125,000 point sign up bonus with a $95 annual fee. They also have a business credit card with a 125,000 point sign up bonus and $95 annual fee.

You can see how just one person can gather several hundred thousand Hilton Honors points – just by meeting a spending requirement. If multiple family and travel buddies do it, you could pool points and live it up in style – wherever you decide to go!

If you’d like to check out these and other hotel credit card options and bonuses, look at “Chip’s Favorite Credit Card Offer$” at the top right side of this website.  Click the “Hotel Rewards Credit Cards”. This will take you to another site where you will see many offers.  Full disclosure: I may get a commission if you apply going through my website’s link, so… Thanks! Email me if you have any questions.

We saw a taping of The Tonight Show Starring Jimmy Fallon. It was last Thursday’s episode with Billy Crystal, Gisele Bündchen and Quavo. We knew a guy, but you can also request tickets here. Don’t cost nuthin’.

Oh, who is that fine looking bespectacled gentleman on the aisle preparing to give some skin to Mr. Jimmy? My expert graphic artist red arrows will point the way.

We also got to see the Dress Rehearsal show of Saturday Night Live – hosted by Awkwafina with musical guest Travis Scott. That was pretty cool. Our show was two hours which Lorne boiled down to 90 minutes. My buddy Cha-Cha hooked us up for tickets, but that is also something you can request.

We hit many restaurants and bars, packed in some art, The High Line, 9/11 Memorial and Museum, and some theatre across the street at the former Studio 54.

With a little planning, you can gather points to fly and stay virtually anywhere for free – just like this Fearsome Fivesome. Please buy our album on iTunes.

Oh yeah… We walked or took the subway almost ever where. At $2.75 a pop, it’s hard to beat. And there’s music! If you liked this story… please share it. Thanks!


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