178. Visiting New York City and Chicago with Kids on Points

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. You can find links to resources mentioned in this episode plus the transcript here: pointstalksquad.com/178 If you're looking for even more Points Talk®, featuring the latest news in points, miles, and credit cards, behind-the-scenes insights, and a monthly Ask Us Anything episode—

You can listen to 178. Visiting New York City and Chicago with Kids on Points online on Radio and Podcast. Open the player on this page to stream the available audio.

178. Visiting New York City and Chicago with Kids on Points is an episode from Points Talk with the Travel Mom Squad by Alex, Pam and Jess.

This episode is 42:45 long.

This episode was published on Apr 28, 2026.

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