It’s everyone’s favorite time again: talking about how I might be moving away from beautiful, cheap, and simple Madison, WI to some bigger city. In this case: Chicago. My vehicle situation, well, it’s not ideal for Chicago.

(I hate my job and have been interviewing in other places to increase my options. I flirted with my hometown, DC, but have settled on Chicago as my next move. Because of reasons.)

I have two cars: a ’13 BMW 135is that’s leased through June 30, 2016; and an ’05 Jeep Grand Cherokee. If/when I get a job in Chicago, nothing about my car situation will have to change immediately. I have ways to make having the 2 cars work until the 135is goes back.

The totally sane, reasonable thing for me to do would be to turn in the 135is as planned, keep my Grand Cherokee I already own, and shut up about cars already. But when it comes to cars, I’m just not that sane.

So let’s say you’re going to be living in a particularly yuppie and/or hipster-infested part of Chicago with many restaurants and bars that use the word ‘artisinal’ to describe things, and where reserving a parking spot in the winter means first digging it out and then putting a piece of lawn furniture in it until you can put your car there. (You might not actually have a lawn, but you own lawn furniture for calling dibs on parking spaces.) You take public transit to work so your car is mostly for running errands and other trips that don’t work for taking transit, or for getting out of the city.


To me, desirable qualities in a vehicle include:

  • Decent-or-better fuel economy
  • Good enough power and handling to hit small gaps in traffic
  • Smooth enough ride to deal with shitty potholes
  • Small enough to parallel park on streets as pictured above
  • 4wd/awd
  • Not too nice because someone’s inevitably going to mess it up
  • Kiiiiiiinda focusing on automatic transmission
  • “Not boring”
  • Let’s say $35k-ish price cap, used but not too old or high mileage is fine

What do you choose?

Option A: My 2005 Grand Cherokee Hemi with 3 eLSDs, beefy winter-rated all-terrain tires, and laughably bad fuel economy. In a way it’s kinda perfect in spite of the terrible mileage. It’s heavy and the brakes are a bit mushy which in heavy traffic makes for some heavy standing on the brake pedal, but uprated pads and stainless lines could help this.


Option B: (your idea, and why)