Using Points for a FREE Trip to NYC Worth Over $1,000

Whenever I think New York, I think pricey.  I'm probably going to take a bus up from DC then I need to hop on Priceline or AirBnB to find a cheap place to stay and that's just to get there and stay there.  Unless I plan on starving myself and sitting in a corner, there's a lot more money that needs to be spent.  New York is so great with so much food and fun but it comes with a cost.  However, the story changes when you have some points to help you out.

Cookie from Levain Bakery.

Today I'm going to share with you guys how I managed to use points to redeem a trip to NYC worth over $1,000 for free!  My wife was already going up for a work trip from Tuesday to Thursday, but we wanted to stay a few extra days to maximize our DINK (Dual Income No Kids) fun before the baby girl comes in May!

Technically, it isn't quite fair that she had a free roundtrip Amtrak tickets.  Nevertheless, I extended our trip so we could stay Thursday to Saturday and got myself there and back for free!  So here's what we needed:

• Hotel for 2 nights (Thursday & Friday night)
• Roundtrip from DC to NY for me

Again, my goal was to not spend any money for the stay and transportation for this trip.  Let's get started by looking at how I booked this trip.

Rowboating in Central Park.

Go to NYC And Come Back For Free

Remember, you always want to gauge how much travel should actually cost before you blindly use points.  That way you have a baseline of how much your redemption is actually worth.  So after looking around I saw that round trip nonstop flights to NY were ranging from $200 to $500.  Next, I looked at how much it would cost to use points.  United and Southwest were giving me terrible redemption options with one way flights going for as little as 10k points and as much as 40k points.

Luckily, JetBlue had just emailed me informing me of a sale that was going on for the next few days! I was able to find a nonstop one way up for only 2,200 points.  Thankfully I had around 3.5k JetBlue points lying around so this was the perfect redemption opportunity.  Normally, this flight would have gone for $138.30! Remember, always be aware of any point balances you have lying around so you can look for options when you book award travel.

Only 2,200 JetBlue Points needed for this flight!

Ok so now I still need to figure out how to get back to DC.  Since I'm out of JetBlue points, I can't capitalize on their ongoing sale, and I'm not too pleased with United or Southwest redemption options.  Instead, now I go over to the Chase Ultimate Rewards Travel Portal.  While their travel portal isn't my go to method of using my Ultimate Rewards points, sometimes you can get good value for short flights.  And what do you know! I find a one way back home on United for only ~6k points.  If I had used United, this flight would have cost ~4k more points.  Normally this flight would have gone for $93.30! 

Only ~6k Ultimate Rewards points needed for this flight!

Stay in NYC For Free

Whenever we stay in NY we like to stay around Midtown between Bryant Park and Hells Kitchen.  This gives us access to a lot of fun stuff and it isn't too far of a subway ride to get down to Greenwich Village, Chinatown, etc. for some good food!

Pancakes, Fried Chicken & Waffles at Clinton Street Baking Company.

So what I need is two nights for free.  Sheesh.  Again, it's definitely a good idea to look on Priceline or other bargain sites to try and get a night for around $150 to $200.  However, this time I wanted it to be completely free.  I remember I have a free anniversary night with my IHG Rewards Club Credit Card that I can redeem at the Intercontinental at Times Square.  So that covers one night.  Phew.  Only one more to go.

Free anniversary night redeemed for a value of $414.47!

I look around on Marriott and Hyatt and it's not looking too good.  I'd have to transfer a minimum of 40k Ultimate Rewards points to make these redemptions.  So again, I look on the Chase Ultimate Rewards Travel Portal.  BOOM. One night at the Iroquois New York for only ~22k points.  Woo! I'm done.  2 FREE nights in NYC and I only needed 22k points and a free anniversary night.

~22k points for a night worth $392.51!

Cool. You got a free trip, but why should I care?
Great question.  3 key things I learned from this experience.

One.  When booking award travel, always be aware of ALL your points balances and any free anniversary nights.

Two.  Pay attention to emails regarding sales for airlines or hotels (especially Southwest and JetBlue).  You can often capitalize on these sales and redeem points for a greater value.

Three.  Don't underestimate the Chase Ultimate Rewards Travel Portal.  Most of the time you get so much more value from your Ultimate Rewards points by transferring over to travel partners.  However, the portal is a good place to check for any possible discounted points redemptions!


I'd love to connect with you on Facebook and hear about your experiences redeeming free travel, fun things to do in NYC, and more!