Carrie sent us this reader success story: Father’s Day in Chicago. She used points and miles to make her husband’s baseball dreams come true. Here’s her story:

I used all the Travel Mom Squad tips to turn a last-minute work trip into a fun Father’s Day weekend! For reference, my husband and I live in Dallas with our two girls, ages nine and six. We have been travelling with points and miles since 2021!

 

Piggy Backing Two Points and Miles Trips

We planned for a year for a three-week trip to Japan and Korea (using Megan’s exact itinerary in reverse). But that’s not what this post is about. About a month before we were scheduled to depart, I received an excellent work opportunity in Chicago that I couldn’t pass up.

However, I was going to have to fly out to Chicago the same day we landed from our direct flight from Seoul. My husband grew up going to Chicago with his family, he’s a huge Cubs fan, and the weekend after my conference was Father’s Day. He was able to fly up two days later with the girls to meet up with me after my conference. We were going to turn this work trip into a family trip!

 

 

Flights

My company reimbursed me for my flights. I flew from DFW on American Airlines to Chicago, and flew home on Southwest® to Love Field.  American Airlines is my favorite airline. I love DFW Airport, and as a card_name cardholder, I appreciate my complimentary access to the Capital One Lounge. I also knew I would need to return to the airport and lounge as soon as possible to decompress, prepare for the conference, and grab a bite to eat.

However, since my husband has the Southwest® Companion Pass through 2025, I needed to fly back on Southwest so that we were all on the same flight back home. He switched his Companion from me to our oldest and booked round-trip tickets with points for him and my youngest.

 

 

Hotels

I stayed at the Marriott Chicago Magnificent Mile for my conference. The hotel was nice, but it was a bit pricey in terms of points to accommodate the entire family. I paid for the hotel with my card_name to maximize my points earnings (and I also reimbursed by my employer).

I wanted to surprise the family by staying at the Hyatt Chicago Athletic Association, a dream of a hotel with a perfect location and amazing Father’s Day vibes. However, we had depleted entirely all of our Chase Ultimate Rewards® points, which we earned from our Chase Freedom Flex℠ and Ink Business Preferred® Credit Card cards, for the trip to Japan. I was able to cobble together enough Hyatt points for one night. My husband, also a Venture X cardholder, had not used his $300 travel credit yet this year, so I booked the other night through the Capital One portal. I emailed the hotel to combine our reservations, and they replied right away, able to do so without any problem.

All information about the Chase Freedom Flex℠ has been collected independently by Travel Mom Squad. The Chase Freedom Flex℠ is no longer available through Travel Mom Squad.

All information about the Ink Business Preferred® Credit Card has been collected independently by Travel Mom Squad. The Ink Business Preferred® Credit Card is no longer available through Travel Mom Squad.

 

 

 

Bottom Line

Without points and miles, we wouldn’t have considered a last-minute back-to-back vacation plan. We would never have spent ~$1,500 after such a large international trip, but it was great to celebrate a great dad for Father’s Day in one of his favorite cities.

Thanks, Carrie, for your Reader Success Story: Father’s Day in Chicago. We loved how you turned points and miles into a fantastic Father’s Day for your husband!

Opinions, reviews, analyses, and recommendations are the author’s alone and have not been reviewed, endorsed, or approved by any of these entities. Terms apply.

 

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