Here Are the Best-Looking (and Most Bizarre) Airbnb Rentals in Chicago

Airbnb rentals may be illegal in NYC, but the DIY-hotel site is still ok in Chicago. Here’s a look at a few standout listings.

photos: courtesy airbnb.com

This studio on La Salle looks fine. Nothing bizarre about it at all. Right? 

A judge ruled this morning that Airbnb, a popular website that coordinates short-stay rentals at private homes and apartments, is illegal in New York City. The service, according to the court, violates a local law that keeps property owners from circumventing the usual hotel regulations.

But Airbnb is still cool in Chicago! In fact, you might be planning to use it to book a stay in town this summer. 

You should be aware that you’re entering a caveat emptor situation here. Sure, you could book a perfectly normal place to stay. But you could also end up at The Homeless Shelter, an Oak Park condo that costs $50 a night to sleep on a floor surrounded by cardboard furniture. Or something like My Couch To Crash on, which is supposedly a couch that you can crash on, for a surprisingly pricy $99 a night. 

The options span a wide range, and it’s a lot to wade through. Plus, who knows if Chicago will be shut down next. So to save you some time, here’s short list of some of the best-looking (and most bizarre) local listings we found in a quick search this morning.  

 


 

 

These look pretty great:

 

HEART OF CHICAGO-LUXURY STUDIO (top of the story): Good-sized studio with ample kitchen space, a clean bathroom, and television. Located in the heart of the city. Perfect for first-time visitors who want quick access to Mag Mile shopping or other tourist attractions. And just about what you’d expect to pay for a decent hotel room in the area. $120/night. 

Gold Coast “OVERLY” Affordable Gem: If the reviews are to be trusted, this South Loop studio lives up to its listing title. The top-floor apartment overlooks U.S. Cellular Field and is within walking distance of the Museum Campus, Soldier Field, and McCormick Place convention center. We’re tempted to book it ourselves now. $89/night.

Lakeview, cottage-like dwelling: So you’ve come to the city, but you want to pretend you’re in a rustic cabin somewhere far away. Luckily, this “cottage-like dwelling” really does look like something you’d find in the French countryside, but with the added benefits of being in the heart of Wrigleyville and having a $99 per night price tag. Breakfast is available in the in-unit kitchen. $99/night.

Private Apartment Hip Logan Square (above): This immaculately designed two-bedroom has a private deck and fully stocked kitchen. The owners live upstairs and emphasize kid-friendliness, offering high chairs and toys their own kids have outgrown. Past guests rave about the apartment and the service they received. $115/night.

Eclectic West Town Vintage Apt: An artistic vibe permeates this listing for a two-bedroom apartment, which comes with a record player (plus the owner’s record collection), Victorian couch, and a homey kitchen space—one reviewer calls it an “antique sanctuary.” $130/night. 

We’re back, we’re better than ever: This Little Village three-bedroom house got nearly 200 glowing reviews before it even had real beds, so it feels like we’re on to something here. Back on Airbnb after a few months of upgrades, the house is directly across the street from the Blue Line and has a fully stocked kitchen, television and internet, and free parking. $109/night. 

Drop-dead fab on the Lake 2bd/2bth: “Fabulous” is really the best word to describe this apartment, where the owner lives part-time with her two young kids. Everything in this place is stylish, shiny, and/or wrapped in yarn. (Really: The kitchen cabinets are covered in colorful, fuzzy threads.) The kids’ room is forest-themed, complete with trees as bedposts, a turn-of-the-century chandelier floats above the dinner table, and the entire apartment is filled with art you can buy or sell to win yourself a free night’s stay. A poodle and eight Betta fish will keep you company when the owner isn’t home. We almost don’t want to tell you how little it costs (but we will anyway): $240/night for both rooms, $90/night for just one.

 


 

 

And these seem a little strange:

 

WRIGLEY LOFT / OR LOFT + SUITE (above): We can’t quite figure out what’s going on with this listing. There are plenty of photos (which reviewers say are fake) and listed amenities (which at least one reviewer claims they were charged for), but the owner’s long, rambling responses to complaints suggest staying here wouldn’t be worth the crazy story you’d go home with. Listed at $1250/night, but “MAKE ME REASONABLE OFFER !!!!!!!!!!!” is the first line in the description.

Air Mattress -FREE Museum & Shuttle: This place looks nice, but the ad itself is for an air mattress in a space shared with an unspecified number of other guests. Plenty of perks, including free shuttle service, free museum passes, Wi-Fi, exercise equipment, cable, and a stocked kitchen, make the unusual sleeping arrangements the least important part of the post. $13/night. 

Hostel Earphoria (for Musicians): Cringe at the name if you must, but this actually looks like a pretty nice place to stay if you’re interested in meeting other music lovers. This Avondale hostel hosts weekly concerts and has recording equipment and a piano, acoustic guitars, and some percussion instruments available to all guests. $99/week. 

Soft moonlit bed under the stars: This is literally a bed under a hallway skylight outside the master bedroom. No door, no other furniture, no assurance another resident won’t wake you up in the middle of the night on a trip to the bathroom. That said, the reviews are positive, so maybe there’s more to this Irving Park roomshare than the unimaginative photos are showing. $43/night. 

Chicago Lakefront Sailing Yacht: It’s not a boat—it’s a yacht. This mobile lodging parks at Burnham Harbor in the summer and has enough room for four people. A certified captain can take you out on Lake Michigan, and the views from the harbor aren’t bad, either. $295/night. 

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