#20: Visiting Chicago With Kids: A Family Guide to Winter Fun, Shopping, and Iconic Sights

Snow falling in downtown Chicago, shopping sprees on Michigan Avenue, ringing in the New Year from a hotel room with skyline views, and ice skating beneath the city lights—this family trip had it all. In this episode, I’m sharing our New Year’s adventure in Chicago with five kids, from staying in a spacious two-bedroom suite at the Residence Inn Downtown Loop to visiting the Willis Tower Skydeck, the American Girl store and café, Millennium Park, Lincoln Park Zoo, and hunting for the perfect slice of deep-dish pizza.You’ll hear how we balanced packed sightseeing days with slow afternoons, why flexibility is key when traveling with kids, and what made winter in Chicago surprisingly magical. I’m also rounding up other must-do family attractions like Navy Pier, top museums, and river cruises so you can plan your own kid-friendly Chicago getaway. 💸 FREEBIE: Get Your Next Vacation for (Almost) FreeBeginner points & miles guide for familiesEPISODE 2: Beginner Guide to Point & MilesEPISODE 10: London With KidsEPISODE 15: Traveling During the Holidays/ Christmas📌 Show Notes 🔗 Episode page: https://www.happylittletraveler.co/podcast/episode20~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~✈️ TRAVEL DEALS & SERVICES🔥 Thrifty Traveler — Flight Deal AlertsGet $20 off your first year📸 Flytographer — Vacation PhotosGet $25 off your first session🎒 Happy Little Traveler Activity Kits (Amazon)Screen-free entertainment for flights & travel days🎁 FREE TRAVEL RESOURCES📱 Must-Have Wi-Fi Free Apps + Travel Apps GuideStress-free travel days for everyone🧠 101 Sanity-Saving Tips for Traveling With KidsPacking, flights, hotels & routines made easier📚 SIGNATURE FAMILY TRAVEL GUIDES✨🧳 Family Travel Made EasyA step-by-step travel-agent-in-your-pocket planning system🖍️ Printable Kids' Travel Activities65+ screen-free pages to keep kids happy on flights & on-the-go🌎 SHOP & FOLLOW🛍️ Amazon Store Front: Our Travel FavoritesWebsite: HappyLittleTraveler.co