My Weekend In The Windy City

Nico In ChicagoIt is 4:48AM in the Chicago O’Hare airport this morning. It’s Monday, so I need to be in the office by 9:00 AM Boston time to meet my fellow co-workers.


My flight home boards at 6:00AM, and I’m surprised to find myself looking forward to crawling into my small coach seat. My time in this non-reclining seat will be my only opportunity for sleep before rushing to my desk to begin my day of work. When my flight lands, I’ll have just enough time to catch the bus and avoid being late.


Two Weeks Earlier…

Rewind the tape two weeks. It’s a Sunday morning, and I’m awake early. Fixing a quick breakfast, I sit down at my computer to write. A client of mine needs ten articles written by the end of of the day and it’s my responsibility to get the work to him on time.


I was unsure if I would be able to create this much content in a single day. There is only so much I’m able to write about the obscure topic my client needs me to deliver.


I spent eight hours writing that day and received a $235.14 payment for my work.


The following Tuesday I wrote three articles for a small teen advice blog. It took me just an hour and I received $81.


The following day, I used a portion of this weeks earnings to purchase my round trip tickets to Chicago. Two weekends later, I was aboard my flight to the Windy City.


Experiencing The Windy City

As my plane touched down, I said goodbye to a girl I had made friends with on the flight and headed into the subway system.


I had no idea which stop I should get off at, but a friendly local on his way home with his sweetheart pointed out a few of the best locations for me to stop.


Willis Tower

Looking out over Willis Tower Skydeck Ledge. (Nothing but a thin layer of glass between me and 103 stories of nothing!)

Over the next two days I visited the 103rd floor of the Willis tower, saw the famous Could Gate sculpture, biked all over the city, and took a tour of the city by boat. I visited Navy Pier to gaze over Lake Michigan, strolled through the Chinatown area in the south, and played pool with some new friends in the Chicago Getaway Hostel.


I forget most of my weekends. Thankfully, I won’t forget this one.


Financing My Trip

The entire trip cost less than $400 broken down roughly as follows…


Round Trip Flight            $170

Hostel For One Night      $50

Food/Dining                      $50

Gifts For Friends             $20

Tours/Attractions        + $70



I earned over $200 for this trip on the Sunday before I left. Working an extra hour the following week cushioned my trip further.


On the Sunday morning in my Chicago hostel I spent another hour writing. I produced three more articles and earned another $81. After I finished writing I went out to explore the city and spend my cash.


I was able to pay for this trip because I was willing to put in a little extra effort. I even saved money in my IRA over this two week period.


One Additional Note

I am currently working a 40 hour per week job and I have yet to spend a dime of this money on travel. I’ve made enough money outside of my normal 40 hours to see the world.


Even if all your 40-hr per week income goes to expenses you can still see travel the world. (at least the United States!)


My hourly rate as a freelancer has steadily increased and I am learning valuable skills that increase my value as a worker. I’m experiencing ‘career development’ at an exceedingly rapid rate. (Recently asking for and receiving a 33% raise!)


It is possible to travel the world while saving for retirement and guaranteeing financial freedom in the long run.


I loved this little trip to Chicago and I plan on hopping on another airplane soon.


Where would you like me to go next?


I’m based in Boston, so my best options are…


  1. Canada
  2. Anywhere in the North-eastern United States
  3. The South
  4. The Bahamas
  5. Bermuda


Let me know in the comments below… Where would you like me to travel next?