1-Day, 4 City Bar Crawl (Chicago Seminars Too!)

In this episode, Mike is joined by former moderator Jackie and her P2 Brent to discuss one of the most creative uses of points and miles you'll hear about — the Mother's Ruin Challenge, a single-day bar crawl across four cities (New York, Chicago, Nashville, and Charleston) all completed to earn free drinks for life. Jackie and Brent break down the logistics, the planning, and how points and miles made the whole thing possible — turning what would have been an outrageously expensive last-minute multi-city trip into something totally doable.Two news items worth knowing: American Airlines appears to be cutting off partner programs like British Airways and Alaska from booking last-minute saver awards within 144 hours of departure, while those same seats remain available through AA's own miles program. On the brighter side, Hyatt is rolling out Advance Booking Access starting June 30, 2026, giving Explorist, Globalist, and Lifetime Globalist members a 13-month award booking window — a full month ahead of everyone else.The episode closes with a spotlight on Chicago Seminars (November 6–8 at the Hyatt Regency Chicago O'Hare), a weekend gathering of roughly 500 points-and-miles enthusiasts featuring sessions ranging from beginner to advanced, manufactured spending discussions, and networking — plus a philanthropic component benefiting select charities. The overarching theme of the episode: points and miles aren't just about saving money, they're about lowering the barrier between "that would be cool" and "I'm actually doing it."Links to Topics DiscussedAmerican Airlines blocking last minute partner awardsHyatt Advance Booking Window for elitesChicago SeminarsWhere to Find UsThe Award Travel 101 Facebook Community.To book time with our team, check out Award Travel 1-on-1.You can also email us at [email protected] your Award Travel 101 Merch hereReserve tickets to our Late Summer 2026 Meetup in Milwaukee now. award.travel/mke2026Our partner CardPointers helps us get the most from our cards. Signup today at https://cardpointers.com/at101 for a 30% discount on annual and lifetime subscriptions! Lastly, we appreciate your support of the AT101 Podcast/Community when you signup for your next card!Technical note: Some user experience difficulty streaming the podcast while connected to a VPN. If you have difficulty, disconnect from your VPN.