178. Visiting New York City and Chicago with Kids on Points
Points Talk®: Your Travel Dreams, Made Possible by Points
Alex, Pam and Jess
4.8 • 1K Ratings
🗓️ 28 April 2026
⏱️ 43 minutes
🧾️ Download transcript
Summary
What's it like to visit a big city with kids, and is it actually easier than it seems? In this episode, Alex and Jess share what it looked like to take their families to New York City and Chicago, and why these trips can be more manageable and fun than you might expect.
They walk through how these trips came together, including how they used points and companion tickets to get there and where they stayed in each city. They also share what worked well when navigating busy destinations with kids, from choosing centrally located hotels to balancing sightseeing with slower, more flexible plans.
You'll also hear real examples of what they did in each city, including Broadway shows, museums, and family-friendly activities, along with tips for getting around and making the most of your time. This episode will give you a better sense of how to plan a city trip with kids that feels both doable and enjoyable.
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Transcript
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| 0:00.0 | Visiting a big city with kids can feel overwhelming at first, but in reality, it's one of the |
| 0:04.9 | easier trips to do and so much fun. Listen in as we share what it's like to visit Chicago and New York |
| 0:11.3 | City with kids on points. Welcome to Points Talk. We are three moms who've discovered how to |
| 0:17.5 | leverage credit card welcome offers to get hundreds of thousands of dollars of |
| 0:21.4 | travel expenses for nearly free. We've used credit card points of miles to take vacations to places like |
| 0:27.1 | Hawaii, Paris, Greece, Maldives, Japan, and so much more. And the best part? We each still have |
| 0:33.6 | 800 plus credit scores. Imagine being able to take the vacation of your dreams for nearly free. |
| 0:39.4 | It's totally possible and we're here to show you how. |
| 0:44.9 | Hey, I'm Alex. And I'm Jess. Let's Talk Points. Alex and Pam recently returned from a trip to |
| 0:51.5 | New York City with Alex's 10-year-old son, and I recently returned |
| 0:55.4 | from Chicago with Ted and Molly and one of Molly's friends. Today, we're sharing tips for visiting |
| 1:01.3 | each of these cities with kids, plus how to make it happen on points. So first, we're going to kick |
| 1:06.4 | off with how these trips came about. So Alex, tell us about how your New York City extravaganza came about. All right. So first of all, you guys noticed it's just Jess and I here today. My mom was on this trip with us, but she's currently in Arizona. And where she's at, she has no internet service. So she was like on a hall spot and we're like, I don't think this is going to work very good. |
| 1:28.2 | Your internet isn't super stable. So we'll just do, we'll just call it and we'll just do this one |
| 1:32.6 | without you. But just know she was on this trip and she's here in spirit. So when each of my kids |
| 1:39.8 | turn 10, my mom and I take them on a trip, just them and the two of us. So this was my son Kai, |
| 1:48.0 | his 10th birthday. It was actually in January, but he for a while has wanted to do New York City. |
| 1:53.5 | And we were thinking, okay, like January, we don't know necessarily if we want to go to New York |
| 1:57.5 | City in January, but let's go in March. So we just postponed it a little bit. |
| 2:03.2 | And yeah, it worked out great. |
| 2:04.7 | So that's how it came about. |
| 2:06.0 | Jess, what about yours? |
... |
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