Chicago Athletic Association: A Hotel Review (And how we Manage Work Travel)

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The Suite I stayed in (Founder's Suite)

In this episode of Travel Party of Five, hosts Raya and Duane dive into a review of the historic Chicago Athletic Association Hotel and share personal experiences and travel tips. Located in downtown Chicago, the Chicago Athletic Association Hotel is a beautifully restored property, originally built in 1893 as an exclusive athletic and social club. Now part of Hyatt's Unbound Collection, it offers unique features that make it a memorable choice for travelers.

Raya provides a detailed account of her stay, including her room upgrade to the spacious Founder’s Suite, which featured two fireplaces, a dining area, and views of Millennium Park. She also touches on the hotel’s blend of classic and modern amenities, from the Game Room, where guests can enjoy shuffleboard and pool, to the historic Milk Room, once a Prohibition-era speakeasy, now serving breakfast and coffee. The hotel’s Shake Shack in the lobby and the rooftop bar with city views add to its charm, making the Chicago Athletic Association Hotel a unique stay in the heart of the city.

The episode also includes practical advice for families managing work travel. Raya and Duane discuss the challenges of leaving family behind and share tips for keeping things running smoothly at home. They highlight the importance of meal planning, family support, and sticking to routines, which help make travel easier on both the traveling parent and the family at home.

While the Chicago Athletic Association offers plenty of character and charm, the hosts note that it may be best suited for adults rather than young families due to its historical decor and lack of child-friendly amenities like a pool. Overall, Raya and Duane agree that the Chicago Athletic Association Hotel is perfect for solo travelers, couples, or groups looking to explore the city with a touch of history.

Whether you’re interested in the architecture of the Chicago Athletic Association Hotel or seeking practical tips for balancing work travel and family, this episode offers insight and advice from experienced family travelers.

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Booking a Trip to Japan on Points as a Family of 5

Thanks for finding our podcast! We are a family of 5 who does most of our travel using credit card points and miles and we share how we leverage credit card offers to earn a ton of points/miles so we can afford travel as a larger family.

Follow us on Instagram @TravelPartyof5

If you’re planning family travel to Japan, this episode is a must-listen! Join hosts Raya and Duane from Travel Party of Five as they break down the details of booking a family trip to Japan for five, all using points and miles. From finding the best time of year to travel to selecting airlines and hotel accommodations, they share each step they took to make their upcoming Japan adventure affordable and memorable.

In this episode, Raya and Duane explain how they decided on traveling to Japan during fall break, avoiding Japan’s busy cherry blossom season and hot summers. Since their family can only travel during school breaks, they chose fall for its pleasant weather and more manageable crowds. They also touch on how they strategized the use of points for their entire family to secure affordable flights without sacrificing comfort. Listeners can learn from their research on airline award programs like American Airlines and Singapore Airlines, along with tips for avoiding high fees by selecting Japan Airlines for their main flights.

One of the challenges discussed in planning family travel to Japan was finding flights for five people on points. Raya shares how she worked through each airline’s award program and explains her top choices based on seat availability and costs. Family travel to Japan isn’t complete without talking about transportation and accommodations, so the hosts also cover how they’ll use points to stay at several Hyatt hotels and how they planned in advance to accumulate the points needed for their stay.

Travel Party of Five also talks about tips for positioning flights, which are often necessary when traveling internationally. They explain how to fly from their home city of Phoenix to San Francisco to catch their Japan-bound flight using Alaska Airlines points, sharing how they scored affordable seats for their whole family. They describe each airline’s booking quirks, sharing a few insider tips, like how American Airlines Japan Airlines award seats tend to show up a day later than expected on AA’s site, making it easier to snag deals if you check back at the right times.

In addition to flights, they outline their Japan accommodations booked on points, including the Grand Hyatt Tokyo, the Hyatt Centric Ginza, the Hyatt House Tokyo Shibuya, and the Hyatt Place Kyoto. Since they hold Hyatt Globalist status, they’re planning to enjoy some perks, including potential free breakfast and room upgrades, making family travel to Japan even more cost-effective.

As a family of five, Raya and Duane know the challenges that come with planning a big trip, especially when it’s as far as Japan. They’re excited to explore Tokyo, Kyoto, and local favorites like ramen shops, convenience stores, and perhaps even the base where Duane spent part of his childhood. They also look forward to sharing their experiences and more Japan travel tips after their trip, helping other families plan their own dream vacations.

Tune in to learn how to make a trip to Japan possible for your family with points and miles! You’ll walk away with practical tips on using points for flights and accommodations, as well as how to navigate travel logistics when you have a larger family. For more tips and to follow along on their family travel adventures, find them on Instagram at TravelParty5.

Visit Arizona: Ride With Us on the Verde Canyon Railroad!

Thanks for finding our podcast! We are a family of 5 who does most of our travel using credit card points and miles and we share how we leverage credit card offers to earn a ton of points/miles so we can afford travel as a larger family.

Follow us on Instagram @TravelPartyof5

All aboard for a journey through Arizona's hidden gem, the Verde Canyon! In this episode, join hosts Raya and Duane as they take you on a journey aboard the Verde Canyon Railroad. As part of their “Visit Arizona” series, they explore this historic train route that travels through the stunning Verde Canyon, often called Arizona's other Grand Canyon. Listen in as they share their experiences, tips, and insights about this unique four-hour train ride, which departs from Clarkdale and travels to Perkinsville and back.

Raya and Duane discuss everything you need to know before hopping on the Verde Canyon Railroad, from the best time of year to ride to what to expect during the journey. They describe the comfortable train cars, complete with air conditioning, champagne, and charcuterie boxes, making it a fun and relaxing ride for travelers. You’ll learn why choosing a seat on the right side of the train offers better views of Arizona’s landscapes, and how each car has access to an open-air observation deck where passengers can enjoy unobstructed views.

As you ride along the Verde River, the train’s guide shares stories about the region’s history, including details about ancient Sinagua cliff dwellings, local mining towns, and the railroad’s origins. Duane even hints at some of the lesser-known themed rides the Verde Canyon Railroad offers, such as Ales on Rails and special stargazing journeys, making it a versatile experience for visitors.

Raya and Duane explain their own journey from Phoenix to Clarkdale, sharing how the trip through Cottonwood added a charming touch to their adventure. While they were hoping to catch some fall foliage, they learned that Arizona’s unseasonably warm weather kept the fall colors at bay. Still, the ride offered beautiful views of red rock formations and lush greenery along the river, a striking contrast to the desert surroundings.

If you’re planning to visit Sedona or Flagstaff, Raya and Duane recommend making the Verde Canyon Railroad part of your trip. It’s an easy day trip from these locations and a great way to see more of Arizona’s varied landscapes. They suggest pairing your train ride with a stay at the Pinion Point, a Hyatt Vacation Club in Sedona, which can be booked using points. After a morning ride on the train, you can head back to Sedona for a nice dinner and complete a perfect day exploring Northern Arizona.

In addition to sharing their personal experiences, Raya and Duane offer practical advice for making the most of your Verde Canyon Railroad adventure. They emphasize the importance of bringing a deck of cards or other activities for the ride, as cell service is unavailable during much of the journey. Their laid-back, honest review helps you decide if this train ride is right for your family, especially if you’re looking for a mix of history, relaxation, and scenic beauty.

Whether you’re a local or just passing through, this episode of “Travel Party of Five” provides all the information you need to plan your trip on the Verde Canyon Railroad. Follow Raya and Duane on Instagram @travelpartyoffive for more tips, answers to your questions, and updates on future episodes.

Tune in to discover why the Verde Canyon Railroad should be on your Arizona travel itinerary, and get inspired to plan your next family adventure.

Hyatt Regency Tamaya & the Albuquerque Balloon Fiesta!

Thanks for finding our podcast! We are a family of 5 who does most of our travel using credit card points and miles and we share how we leverage credit card offers to earn a ton of points/miles so we can afford travel as a larger family.

Follow us on Instagram @TravelPartyof5

In this episode of the Travel Party of Five podcast, hosts Raya and Duane share all the details of their recent weekend getaway to New Mexico. They take you through their stay at the Hyatt Regency Tamaya and their very first visit to the Albuquerque Balloon Fiesta. This episode is a must-listen if you’ve ever thought about experiencing the excitement of hundreds of colorful hot air balloons filling the sky.

The Hyatt Regency Tamaya is located just outside of Albuquerque, and it became the perfect home base for their trip. This family-friendly resort offers beautiful mountain views, plenty of activities, and a relaxing atmosphere. From horseback riding to cozy fireplaces, this property has something for everyone. Raya and Duane used their points to book a stay here, and they share tips on how you can do the same, especially if you're aiming to attend the Albuquerque Balloon Fiesta. With features like multiple pools, bike trails, and even s’mores nights, the Hyatt Regency Tamaya makes it easy for families to enjoy their stay while exploring the area.

The main highlight of their trip was attending the Albuquerque Balloon Fiesta. This world-famous event runs for nine days each October, with sessions in the early morning and evening. They describe the unforgettable experience of waking up at 2:30 AM to catch the first bus to the event, and the thrill of watching the mass ascension where hundreds of balloons take off together. Even with the early wake-up call, they agreed it was worth it. They explain the options for getting to the festival, including the convenience of using a park-and-ride system to avoid traffic.

During the episode, Raya and Duane also share practical advice for attending the Albuquerque Balloon Fiesta, like dressing warmly, packing patience for crowds, and booking everything in advance. They recommend at least one morning session and a night session if you want to experience all the magic the event has to offer.

Tune in to this episode to hear more about the Hyatt Regency Tamaya, the Albuquerque Balloon Fiesta, and tips on how to use points and miles to make the most of your family travels. Raya and Duane share all the highs and lows of their trip, from delicious New Mexican food and drone shows, to the chilly, early morning balloon launches. They hope this episode inspires you to plan your own adventure to New Mexico and discover the charm of the Hyatt Regency Tamaya and the Albuquerque Balloon Fiesta.

So, if you're planning a family trip or looking for your next destination to use points and miles, this episode will give you plenty of insights. Don’t miss their advice on how to make the most of a short weekend trip, tips on booking with points, and why the Hyatt Regency Tamaya is an ideal choice if you’re visiting the Albuquerque Balloon Fiesta.

Replay: How to Earn the Southwest Companion Pass

In this episode, we’re revisiting one of the most valuable tools for frequent family travelers—the Southwest Companion Pass. If you've been wondering how to earn the Southwest Companion Pass, or you're looking to maximize your travel savings, this episode is for you.

We share our  personal experiences as a family of five, highlighting how earning the Southwest Companion Pass has made a huge impact on our travel plans. We explain how it allows us to fly with one companion for free (except for taxes and fees) on every Southwest flight. Since earning their Companion Passes in early 2023, they’ve traveled to destinations like Maui, Costa Rica, and Washington, D.C., only paying for a fraction of their family’s flights.

If you’re new to this game-changer, we break down exactly how to earn the Southwest Companion Pass, covering the most important steps like when to apply for Southwest credit cards and how to meet the minimum spending requirements. Timing is critical, and Raya and Duane explain how to maximize your travel benefits by planning strategically, especially if you're a larger family like theirs.

Here’s what we’ll cover in this episode:

  1. What is the Southwest Companion Pass?
  2. How to Earn the Southwest Companion Pass: We walk you through earning the 135,000 Rapid Rewards points needed within one calendar year. Raya also explains the alternative way to earn the Companion Pass by flying 100 Southwest flights, though she acknowledges that’s a harder route for most families.
  3. Maximizing the Companion Pass for Two Years: Learn why applying for the right Southwest credit cards at the right time can help you stretch the benefits for almost two full years.
  4. Who Should (and Shouldn’t) Get the Companion Pass: Raya and Duane explain how the Southwest Companion Pass makes sense for people who frequently travel to domestic and nearby international destinations. They also discuss how it may not be the best fit if you don’t live near a Southwest hub or prefer long-haul international travel.

One of the most crucial takeaways from this episode is understanding the best time to apply and spend on your Southwest credit cards. Raya stresses that if you want to earn the Companion Pass for the maximum amount of time, it’s important to ensure that your points hit your account after January 1st, so you can enjoy the pass for two full years.

Throughout the episode, they also share their personal strategies and a mistake Raya made when they first earned their passes—one she wants you to avoid. Whether you’re aiming for more frequent family vacations or planning weekend getaways, this episode is packed with tips on how to earn the Southwest Companion Pass, how to use it, and why it’s a game-changer for larger families.

If you're thinking about applying for Southwest credit cards, now is the time to start, so you can begin earning your Companion Pass for next year. As always, feel free to message us on Instagram at @TravelPartyof5 if you have any questions about how to earn the Southwest Companion Pass. We’re here to help you make your family travel more affordable!