Starting Small: How I Booked My Family a Weekend Trip to Chicago for $22.40

#27 This week on Rewarding Routes, we're keeping it close to home...literally.In this episode, we're talking about starting small with points and miles. We'll break down how I booked a Chicago weekend trip for my family using two cards most beginners can actually get, discuss how Companion Pass works and why it's one of the best deals in travel, and share why a $22.40 domestic trip might be the most important booking I make all year.Tune in to learn how to build real confidence with points and miles so when Japan is finally on the calendar, you're ready.What You'll Learn from This EpisodeHow to earn and use Southwest Companion Pass to fly your partner for freeWhy signup bonuses are the fastest way to accumulate points and milesHow to book hotel nights through Chase Ultimate Rewards and transfer to HyattWhat to know about flying with a lap infant before your first family tripWhy starting with a simple domestic trip is the smartest first step toward JapanFeatured on the ShowSouthwest Rapid Rewards Plus CardChase Sapphire PreferredFollow John on Instagram — @itsjohndiazEmail the show — [email protected] Routes Stan Store  → https://stan.store/rewardingroutesInstagram → https://www.instagram.com/rewardingroutes/Email → [email protected]