With our Emirates flight booked, we just need to find flights to and from New York.  It seems a little early to book, and the fares are a little more than I want — around $300 per person, each way on various airlines, or about $1200.  Discount airline Southwest is an option, but their schedule is only open until May 8th, 2017.  So other options:

1.  Use the Alaska Airlines companion fare for $121.  Lisa pays the regular round trip fare, and then I pay just $121.  Current Alaska Airlines single fare is $540, so with the companion fare the total would be around $665.  Not bad, but I know that I can do better.
2. Use my Ritz-Carlton Visa card and make my reservation through their discount air portal.  I can book with most major airlines except Southwest, Spirit and Frontier.  Using their service will give me a $100 discount for two, round-trip tickets.  Using the Alaska scenario above, two tickets at $540 and minus $100 will give me a total price of $980.
3. Use my Citi Thank You Points.  I have 50,000 points, and using their booking engine I can book American Airline tickets at 1.6 value.  That means every Thank You point is valued at 1.6 cents, giving me 50k x .016 = $800.  So if I find tickets on American Airlines that would cost $600 in real money, I can use 37,500 Thank You points.
4. Use my Chase Ultimate Rewards to either transfer points to an airline mileage club or use the web travel portal and book directly.  I have 50k points, which equals $500 towards airfare.
5. Use my Delta Airlines Skymiles to book an award ticket.  I have 25k miles, which is enough for two one-way tickets at 12,500 points each.

After evaluating all our options, I decided to go ahead and book the first leg of our trip to New York using Delta Airlines award miles for two one-way tickets.  We will take a red eye flight leaving at 12:50am on Monday, July 3rd and after a connecting flight in Minneapolis, we will arrive at JFK at 11:00am.  That will give us the rest of Monday, all of Tuesday and part of Wednesday to enjoy New York.  I am particularly interested in seeing some fireworks over the Statue of Liberty, but we’ll have to be smart and look for a hotel that might be able to offer views and a reasonable cost for two nights.

Lisa and I have been to New York a few times before so there is nothing “must-see” that is on a bucket list, but we would like to check out the Guggenheim Museum, the Met and/or maybe do one of those touristy open air bus tours.  We’ll see.  The most important thing though is that we gave ourselves enough time to arrive to New York a couple of days before our international flight, so any airline delays or cancellations should be mitigated enough for us to make the Milan flight, knock on wood.

So there you have it.  We are slowly building our summer plans by booking our major transportation — we still have return flights from New York to take care of, but we have plenty of time and we still have a number of possibilities on what we might want to do in New York when we get back and for how long.  So far the trip this trip has costed $895 + $5.60 = $901.06.

Flight details:

DELTA 2520
MAIN CABIN (N)
PORTLAND, OR
12:50am
MPLS-ST PAUL
6:05am

DELTA 1563
MAIN CABIN (N)
MPLS-ST PAUL
7:00am
NYC-KENNEDY
10:49am

CHARGES
Air Transportation Charges
Base Fare
$0.00 USD
Taxes, Fees and Charges
United States – September 11th Security Fee(Passenger Civil Aviation Security Service Fee) (AY)
$5.60 USD
Total Charges $5.60 USD
TOTAL TICKET VALUE 11,500 Miles and $5.60 USD