Before my 6 year journey in Chicago came to its end, I knew I needed to send her off right. I needed one last culminating event that represented my experience there all together. I needed to say, “Thank you, Chicago for keeping me alive through the most absurd years of my life!

Chicago was an unplanned risk, an underestimated fork in the road, a blur of good and bad, chaotic and illuminating, but somehow after the twists and turns, ups and downs, I unclenched my eyes, looked to the ground and surprisingly found my feet firmly planted.

I couldn’t think of a better way to say au revoir Chicago, than to free fall for 9 thousand feet, pull my own shoot, and with a sign of relief, enjoy the rest of the view in tranquil contemplation and complete awe, not just for being alive, but for such an incredible ride. So in honor of all Chicago has meant to me, I jumped out of a plane.

A very brief history ( you may skip this part if you’re only interested in the sky diving details. It’s very self indulgent and only talks about myself):

(more…)

When: Every Tuesday from Mid-July to Late-August at Sunset

Where: Grant Park  (and various other neighborhood parks)

Cost: Free!

City vacations inherently seem to consist of lots of walking, little relaxing, obnoxious maps, dinner plans, crowded sidewalks, and ultimately obstructed views-but they don’t have to.   While the hustle bustle of a city can be invigorating, too much of the head-spinning activity can be nauseating.  A movie in the park is the perfect opportunity to drop the shopping bags and recharge that ambitious battery.

Each summer the Chicago Park District shows 170 classic movies in neighborhood parks across the city. Grant Park is an ideal location for visitors. It’s right downtown, offers a classic panorama of the night skyline, and is so close to all those touristy hotspots, it’s easy to check a few off the list on the walk there, such as Buckingham Fountain and Millennium Park (to see that huge bean!).   It would also be a nice conclusion to a day spent at the Art Institute (my favorite Chicago Museum).   Get there a little early to set up. Bring a blanket, a little picnic, and relax.

This is sounding entirely to wholesome for one of my recommendations so let me tell you the best part, besides it being free. It’s also…..brace yourself…..BYOB!  Bring you own beverage!  Okay, Okay, notice I said beverage, not booze.  It’s a city park so technically no booze allowed.  Technically.  I’m a firm believer in only following the rules that I believe make sense.   My friends and I have always brought beer and/or wine and we’re yet to be accosted by the city park enforcers.  Common sense applies.  Be courteous, mind your manners and don’t leave any messes.

Kids are also welcome, and if you’re lucky they’ll just fall asleep since most of the movies are black and white and children would rather play backgammon with grandma than watch old films.

The Aloft : El Circo Cheapo Cabaret
Price: $10.00
Website and Reservations for “the list”: http://elcircocheapo.com/home.html

Picture this: an abandoned-looking warehouse and a dimly lit alley. A juggling clown stands outside a small side door with a few of his cigarette-puffing friends. This is the guy with “the list.” Intrigued? Damn right, you are.

It’s the poor man’s Cirque De Soleil. Come inside to find trapeze and silks, lights and equipment dangling from rafters. Have a seat on a random couch, folding chair, gym mat, or floor when the lights dim and the ring mistress enters and enjoy the show that takes place practically right above your head. It feels a little like something out of “Fear and Loathing in Las Vegas” but that’s for another day. Want to hear the best part? It’s BYOB. That’s right, Bring Your Own Booze! Sounds a little boot-leg, right? Well, lighten up because it is, but I can assure you that while the cost is cheap, the talent is not. This is a truly unique experience and you will leave with that holy-shit-that-was-cool feeling. What the hell, you can even bring the kids*.

* I have no kids but am pretty good at taking care of my plants, however I overwater them before I leave for trips and have killed one or two that way. Anywho, I’m not sure I would trust my advice on the rearing of children or the appropriateness of cabaret content. There are R-rated jokes and scantily clad circus women, but it can’t be any worse then those HBO specials they watch while you’re sleeping. I found them quite informative as a child and turned out just fine.