You’ve seen my version of tourism in D.C., Minneapolis, Kansas City, and Denver. This time, I was in the Windy City for four days, and it didn’t disappoint.

On the drive up, we passed this very pretty Chevelle SS rocking Swiss plates:

Our first order of business in Chicago was a Jimmy Buffett concert, which was a ton of fun as always. In attendance we found a BMW X6M, which has to be the fastest dorky car ever.

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There was also a Golf GTI Fahrenheit Edition:

And a mildly hotrodded International Travelall.

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Bonus: This police Suburban was directing traffic. Looked to be in good shape.

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The sound made up for the chintzy wheels.

A bit of Rollandbait near Wrigleyville. Sorry for the smudged lens.

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ID this cool old bike?

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Fantastic Mercury Cougar convertible.

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Everything below this line was spotted within a two hour period.

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Yet more Rollandbait. I mean the restaurant as well as the car.

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I’ve seen so many 80’s 911s lately it’s getting ridiculous. People must think they’re about to appreciate.

Badass G55 AMG.

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The color combo on this Bentley is sublime.

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ALL THE BRAKE DUST!!!

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Too bad these were such shit, because regardless of what anyone says, they are extremely beautiful. Attention-getting, to say the least.

Itsy bitsy.

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Sounded spectacular echoing off the buildings. Driver got on it.

I had to stop twice while photographing this Wraith.

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Once to get a picture of the passing Alpina B7...

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and then because a cyclist lady yelled at me for being in the street. Totally worth it.

I like the color, but sadly it wasn’t a gated manual.

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That is one fast boat.

This manual twin-turbo RX-7 had just 12k original miles and looked like it had zero. It turned out to belong to a dealership on the other end of the building who just got it in. The salesman very graciously showed us all around the car, which had apparently come from the collection of a local man whose collection was worth “hundreds of millions of dollars.” I can honestly say this was the cleanest 90’s car I’ve ever seen.

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CL65. Again, pardon the huge wheels.

This grey Huracán passed us several times. Jetta my ass.

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We also stumbled across Gold Coast Auto Gallery, which specializes in selling absurdly expensive cars to the ridiculously wealthy. I know that most people on Oppo don’t care for such vulgar showpieces, but here you go anyway:

The G63 was a privately owned car that just happened to be across the street.

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For the record, the employees at Gold Coast were nothing but welcoming and happy to answer any questions I had. They were the complete opposite of snobbish. I only took a picture of a couple of the cars, but they had plenty. All in all, a good trip.