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Chicago’s Wackiest Airbnbs

So you didn’t book the Wienermobile. There’s still a boat, or a tiny house, or a rooftop, or a trailer.

By now, you’ve heard the news. In honor of both National Hot Dog Day (July 17) and Lollapalooza (August 1 to 4 in Grant Park), a major purveyor of encased meats is turning its famous marketing vehicle into a short-stay rental.

That’s right: From August 1 to 3, Oscar Mayer’s 27-foot Wienermobile — one part PR gimmick, one part tour bus, and 100 percent Americana — will camp out in Chicago as a stationary Airbnb rental.

Unfortunately for many would-be sausage bus campers, the Wienermobile’s three available dates were quickly booked up. The good news: there are plenty of other wacky places to spend a night or two in Chicago.

Vibing on the tiny house trend and want to stay in a structurally questionable backyard abode? No problem! Fixing to kick back in a vintage RV camper? We’ve got that too. Or maybe, like our departed friend Chance the Snapper, you prefer the water. How about a couple nights in 33-foot cabin cruiser?

Currently, there are 29 listings highlighted as “unique stays” in Chicago on Airbnb. Here are a few of the most unusual.

Pitch a tent on a Chicago rooftop…

This open-air rooftop can be yours for $77 a night, but you’d better like urban camping, because you’ll have to bring your own tent. Included in the stay is Wi-Fi and a direct view of the Chicago skyline — a nice touch.

According to the listing, the rooftop has no shower access, but if you ask nicely, maybe the homeowner will let you borrow the garden hose.

Crash in a retro RV camper…

Here we have an old-school travel trailer for $58 a night. Amenities include a window-mounted AC unit, microwave, mini-fridge, and an electric composting toilet. The camper is located in a backyard that doubles as an urban farm, complete with chickens and raised garden beds. It’s not exactly the Wienermobile, but it’s close enough.

Sleep in a slipshod shack…

Described in the listing as a “rustic tiny house,” this reclaimed lumber and plywood structure looks a bit like the Unabomber cabin. But for only $60 a night, you at least get a private space. There’s also access to a real toilet here, as well as coin laundry.

Bob on Lake Michigan…

Nautical Airbnbs aren’t exactly new, and if you’re looking to stay in a sailboat or cabin cruiser in Chicago, there are plenty to choose from. This $245-a-night option sleeps up to four guests below deck of a docked 42-foot sailboat. (If you want to go for a cruise, you’ll have to contact the captain.) The interior is nice, as are the views from Burnham Harbor. Dates are still available for Lolla, so jump on it.


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