The Traveling Family Circus: Your Go-To Guide for Stress-Free Family Travel
Welcome to The Traveling Family Circus, your go-to podcast for stress-free family travel tips, budget-friendly vacation ideas, and must-know hacks for traveling with kids. Tune in each week for destination guides, packing tips, and real-life stories from a family of seven exploring the world together and making memories.
The Traveling Family Circus: Your Go-To Guide for Stress-Free Family Travel
#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.
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Beginner points & miles guide for families
EPISODE 2: Beginner Guide to Point & Miles
EPISODE 15: Traveling During the Holidays/ Christmas
📌 Show Notes
🔗 Episode page: https://www.happylittletraveler.co/podcast/episode20
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