39. Roadtrip on Points: How Jess's Family Road Tripped To Chicago
Points Talk®: Your Travel Dreams, Made Possible by Points
Alex, Pam and Jess
4.8 • 1K Ratings
🗓️ 29 August 2023
⏱️ 36 minutes
🧾️ Download transcript
Summary
Hey there, it's the Travel Mom Squad—Alex, Jess, and Pam! Everyone has different preferences when it comes to travel. Some prefer the efficiency and speed of flights, while others enjoy the adventure and unpredictability of a road trip. Today is all about leveraging the art of award travel for road trips!
Jess's recent journey is a perfect example. She and her family decided to drive from Houston to Chicago.
More impressive is how Jess made the most of her points. She used them to stay at unique places like the Caption Hotel in Memphis, and didn't stop there. In Chicago, she managed to stay at the upscale Thompson, right in the heart of the city, again using her points.
Chicago itself is a delight. Apart from its many attractions, what stands out is how easy it is to get around. The city's efficient public transportation means that even those who drive into the city (like Jess) can park their cars and move around without them.
However, traveling, especially by road, comes with its set of challenges. For those with kids, keeping them entertained and comfortable is crucial. Alex offers some practical tips in this area.
Hit play to learn about how your next roadtrip can be affordable and memorable! Whether you're up in the air or on the road, the adventure awaits. Happy traveling! :)
Links For All Things Travel Mom Squad: stan.store/travelmomsquad
Links For This Episode:
How I Earned Two Free Nights by Paying My Taxes: https://travelmomsquad.com/how-i-earned-2-free-hyatt-nights-by-paying-my-taxes/
Hyatt Centric Magnificent Mile
Episode Minute By Minute:
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0:02 What's inside today's episode!
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02:38 Jess shares about her latest trip to Chicago!
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05:22 Jess dishes on the Caption Hotel in Memphis
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07:49 Jess stayed in downtown Chicago for the first four nights
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09:08 Jess shares how to consolidate earned free night stays into one reservation
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11:15 Jess breaks down how her and her husband earned free nights with Hyatt
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14:15 Hyatt Place downtown is another great option for larger families
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17:41 Jess and Alex breakdown all the great options for Hyatts in Chicago
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22:22 Jess shares some family friendly things to do while in Chicago
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28:12 Public parking is expensive downtown so utilize public transportation
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30:59 Alex shares some road trip tips for large families with kids
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32:36 Jess shares an app called Spot The State
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34:47 Using points and miles on a family road trip can save you hundreds of dollars!
Transcript
Click on a timestamp to play from that location
| 0:00.0 | You're listening to Points Talk with the Travel Mom Squad, previously known as the Travel Hacking Mom Show. |
| 0:05.8 | Follow the links in the show notes to stay up to date with what the Travel Mom Squad has been up to. |
| 0:10.6 | Sometimes rather than redeeming points and miles for flights, some of us may feel like redeeming them for a good, old-fashioned American road trip. |
| 0:19.6 | Listen up as Jess discusses her recent road trip to Chicago |
| 0:22.7 | and how she utilized points along the way. We'll also discuss some of our favorite things to do |
| 0:27.2 | in Chicago and some helpful road trip tips. Welcome to the Travel Hacking Mom Show. We are three moms |
| 0:33.4 | who've discovered how to leverage credit card welcome offers to get hundreds of thousands of dollars in travel expenses for nearly free. |
| 0:40.4 | We've used credit card points and miles to take vacations to places like Hawaii, Paris, Greece, the Maldives, Italy, and so much more. |
| 0:47.9 | And the best part? We each still have an 800 plus credit score. |
| 0:51.7 | Imagine being able to book a vacation without having to check your bank |
| 0:54.6 | account. It's totally possible and we're here to show you how. Hey, I'm Alex. And I'm Pam, Alex's mom. |
| 1:01.6 | And I'm Jess. We are travel hacking moms. So just recently returned from a road trip from |
| 1:07.8 | Houston to Chicago. So we thought it would be fun to recap how she used |
| 1:12.0 | points to save on hotels along the way. And then we'll go over some road tips for families. |
| 1:17.8 | I just want to start this off by saying, I hate road trips. You won't find me doing a road trip. |
| 1:25.7 | So just more power to you doing this. Alex only lives |
| 1:31.5 | seven hours away from me. I won't even do a road trip to visit her. And my husband always says, |
| 1:37.6 | why don't we just drive? By the time we drive to Denver and we wait for our plane and we fly there, we could have already driven |
| 1:48.2 | there. And I'm like, nope, not going to happen. I want to go to my lunch and I want to be able to |
| 1:57.0 | not feel course. I want to be able to work on the plane. I like my airport trip. So it's not |
| 2:04.9 | going to happen for me. Well, and when you said you were going on this trip, this road trip, |
| 2:09.4 | I was like, what? This does not sound like Jess. I cannot believe she's driving. What did you say? |
... |
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