A peek into my FREE ride to Chicago…

A peek into my FREE ride to Chicago…

Hello on Sunday, and happy Mother’s Day to you wonderful women out there!

Here’s a quick look into how I literally traveled (for FREE) to Chicago. Watch me act like a country bumpkin: “ooo, there’s food!”

Plus, there are my pictures from Chicago over HERE.

Want to learn how to travel for free, yourself? I can help.

Oh, and my backpack does weigh 40 lbs! Guess I don’t have to worry about working out every day. :-)


Thanks for watching!


Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad - looking to improve myself, have fun and serve others.

8 comments on “A peek into my FREE ride to Chicago…
  1. Travel-for-free wannabee says:

    Looks like a great way to travel and an adventure in itself. Thanks for the insight!

  2. Shannyn says:

    I was so surprised when I wanted to take a train from San Diego to Washington State how expensive it was! I had no idea…when you also factor in time off work (if you have to take any) and food, etc…it adds up! I would LOVE to take a train though- if I could find a way to do it for cheap/free! :) Thanks for posting!

    • Nathan says:

      i know, the prices are crazy. it’s like travel is only reserved for the rich. but not anymore! :-)

      there ARE definitely ways to do this for free – i’m actually about to book an even more expensive trip from Chicago to Portland in a sleeper car – again, for nothing! It’s all about knowing how to earn the points for little-to-no-money, and then redeeming them for great rewards. I’ve been learning about this for the last couple of years. For me, it is so. much. fun!

      thanks so much for reading, and would love to help you earn some free travel – something we can talk about in person! :-)

  3. Yeah Nathan! That is a nice little temporary home there. I’ve been thinking that I would love to take a train from coast to coast (East-West). I’ll let you know if I ever pull the trigger on it. :-D

    How do you like traveling alone by the way? My first international trip to Ireland was by myself and my second trip was with people. They were very different experiences. Have a great time at all your stops!

    • Nathan says:

      thanks stephen! i actually just booked my next train trip: a sleeper car (similar to the one above) from Chicago to Portland – and once again, for FREE! There aren’t many stops of any length on this route, but I’m sure the scenery will more than make up for it.

      It’s very cool to travel this way and love that I will have done the East-West route you mentioned, even for much less than driving. :-)

      I really love traveling solo. It also helps that I love meeting people, and I have tons of opportunities to do that, but silence and personal time are golden for me. Having my own space on the train provided a great getaway and a chance to rest before I went out and socialized again!

      Thanks for the well wishes!

      • Very very cool Nathan. I can understand why you like traveling alone as meeting people was the highlight of my Ireland trip.

        And wow, that’s awesome you’re going coast-to-coast! What an interesting and exciting life you have. :-)

        • Nathan says:

          haha. thanks stephen. :-)

          i’m just taking it one day at a time – looking at what really excites me and I’m passionate about, and following that. Some days, it’s clearer than others what to do. Gotta keep chugging along…thanks for the support!

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