My Debt Free Staycation

This past week I unplugged. My wife and I have spent the better part of this year paying off her student loan and the only vacation we had taken up to this point was a Memorial Day weekend scouting trip to Charlotte, North Carolina to see if it could be our future hometown.

So we approached this past week with a do-nothing and enjoy life attitude from the comfort of our current city, Chicago. With a budget of just under $100 a day (all paid for in cash!) we dined at some new (and old time favorite) restaurants, took in some great views of the skyline from rooftop patios, hit the beach, volunteered at a local food pantry and I took time to reconnect with my wife.

I’ve said it before here and I’ll say it again: The main driver of my total money makeover and pursuing wealth building is to get my time back. This past week was a great taste of what I’m striving for. Sure, the rooftop city views were dazzling and checking out the finer points of our favorite neighborhoods is fun, but for me the best part of the week was getting to spend as much time as I could with my wife and consequentially remembering why we work so hard and place a top priority for saving for our future.

It has been incredibly important for us to have taken reasonable vacations over the last few years. The time-outs, breathers and adventures have collectively gathered as one big “atta boy” for me. Staying motivated with written goals and clear timetables as well as brief glimpses into the future have helped me keep my sanity and discipline in wealth building.  

But to get away from being nerdy, here’s a quick rundown of some of my favorite places from the week, if you happen to find yourself in my fair city:

The Roof at The Wit

201 N. State Street

Drinks are pricey but the views and décor aren’t too shabby for a lounge in the loop. I went during the week right when doors opened at 4pm. You’ll get in ahead of time before the after-work crowd converges and have your pick of the place of which gorgeous view you want to take the city in from.

J.Parker at the Lincoln Hotel

1816 N Clark

Pricey as well and centered in yuppie-fied Lincoln Park. Pretentious…check! Overpriced…certainly! But stunning views overlooking North Avenue beach and the East end of the skyline is lovely on a cloudless afternoon. Oh, and if you prefer a sweet and sparkling drink to imbibe on, and it’s in the budget, go for the Bellini, you’re welcome.

Violet Hour

1520 N Damen

While I am more of a wine and beer fan and think that everything on this menu tastes like fire, the ambiance in this Wicker Park establishment is second to none. If you get there early enough to avoid the crowds and find the door (I didJ) you will love this gem.

Adriatic Restaurant

5553 N Clark

And it just wouldn’t be a trademarked review from me unless there was a bargain somewhere in the mix! This awesome place is near the north end of Andersonville and does everything right. Ambiance is amazing as my wife and I had drinks on the outside patio, and as lovely as the coy pond was I was even more in awe of the beautiful décor on the inside. Prices are unbelievably reasonable and their Sangria might just be the best in the city, you’re welcome again! J