Sending my Wife and her Best Friend to the Windy City

A couple of weeks ago, Kristin told me that her and her best friend, Hailey, wanted to take a trip together to celebrate being best friends for 15 years. They had a few locations in mind, but after a couple of weeks, they decided on Chicago. After they decided on a location, I started looking at hotels and airfare to get them there. There are many options for flights and hotels in Chicago, so how did I get them there?

Kristin and Hailey had been talking about a trip for a while and to make sure I could book the trip they wanted, I opened 5 cards in May. This gave me plenty of points for them and to have extra for us later. They are really excited for their trip and I am happy that I have earned enough points to book their trip.

Booking the Airfare:
There aren’t many airlines that fly non-stop or direct out of Manchester, but Southwest actually flies non-stop from Manchester to Chicago (in about 2 hours!). They are usually the lowest cost for flying out of Manchester as well. After doing some searching, Southwest was the airline I would be using to book their flights.

When I opened our American Express Premier Gold Rewards credit cards (one for each of us), we received a $100 airline credit on each card. So, I bought 2 $100 Southwest gift cards. After our trip to New Orleans, I had a $75 voucher as well for our flight being delayed. We also have enough Ultimate Reward points which transfer 1:1 to Southwest.

Cost in points
Cost in points

When booking their flights from Manchester to Chicago, I had to decide if  I would use points and gift cards for this part of their trip. I played around with some numbers for a few minutes, but quickly found my answer. It would either cost 12,880 Southwest miles or $226. For this part of their trip, I decided I would use our points. I redeemed for a value of 1.67 cent per point. 

Actual cost
Actual cost

When booking their flight home, I tried to use some of our American Airline miles  but there weren’t any saver awards. Again, after looking I saw Southwest was the best option to fly them home. I decided to book them evening flights, rather than morning flights, so they could enjoy their morning and part of the afternoon in Chicago.

Cost of flight
Cost of flight

The flight home would cost 17,698 points which is not a bad price for 2 one way tickets or $300. Most airlines cost 12,500 miles for an award saver one way ticket. I had $275 in Southwest gift cards/voucher money to use. I decided I would use the gift card/ voucher to fly them home. If I were to redeem points, I would have redeem at 1.63 cents per point. 

I could have used my gift cards for the first part of their flight and had it completely covered, but it makes more sense to use the gift cards on their flight home. By using the gift cards on the way home I spend $25 but I save 4,818 Ultimate Reward points. Those are worth $48.18 if you were to redeem for cash, even more if you use their transfer partners.

Cost of flight in points
Cost of flight in points

The actual cost of the round trip flights would have be $526. The total airfare cost was $36.20, which is 6.8% of the actual cost.

Booking the Hotel:
There were so many hotel options in Chicago, we have Ultimate Reward points that we could use for Hyatt and we have IHG points as well. After looking at the different options, I decided to book them in a Hyatt hotel. Hyatt has great hotels and awesome customer service and when using my points, they give me one of the best values. IHG has some great hotels as well, but overall Hyatt has nicer hotels (IHG has some great properties as well). Since I wanted them to have a great time and have a really nice hotel experience, Hyatt won this time.

There were a few Hyatt hotels I looked at, but decided on the new Hyatt Centric, which opened in April. The hotel and rooms looks awesome and had great reviews as well. I wouldn’t expect anything else from Hyatt.

Actual cost of the room
Actual cost of the room

Hyatt is a transfer partner of Ultimate Rewards (probably their most valuable transfer partner!) at 1:1 ratio. Since we still had plenty left over after redeeming 12,000 for our Southwest flight ( I had some points left over in my Southwest account), I had no problem spending 15,000 points per night on this room. Especially when you take into consideration it would be over $1,000 for their stay. 

Cost of the room in points
Cost of the room in points

I had about 2,000 Hyatt points in my account, so I transferred 43,000 Ultimate Reward points to my Hyatt account. The actual cost of the hotel room would have been $1078.94, but instead we redeemed 45,000 points. I am always happy when I get a value over 2 cents per point and  I redeemed these Hyatt points, at 2.4 cents per point.

In total, I was able to get my wife and her best friend a 4 day/ 3 night trip to Chicago for 57,000 points and $36.20. This definitely beats spending $1604.94 for a trip!

If you have any favorite spots or can’t miss things to do in Chicago, please leave a comment!

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5 thoughts on “Sending my Wife and her Best Friend to the Windy City

  1. Excellent post! Thanks for the thorough explanation. I hope your wife and her best friend have a fantastic trip.

  2. Excellent post! Thanks for the thorough explanation. I hope your wife and her best friend have a fantastic trip.

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