If you’re in Chicago a few days with friends, (especially Uptown/Wrigleyville), I highly recommend staying at Tomasso’s place!
This home is spacious, comfortable, and charming. There’s more space than you think there is, and while it’s a shared living space with the owner, everything you need to use is private (like a classic B&B setup).
Tomasso communicated when he would be at the unit, but for reference, we stayed 3 days and didn’t see him beyond the quick and friendly check-in on day 1.
There’s a gated parking spot out back, which we had unlimited access to. If you have a car, don’t skip that!
It’s also full of “antique store” charm – lots of disparate styles and decor line the walls, from marble busts and antique furniture to painted porcelain and a poster of Chris Rock’s character from the Fargo TV series. I found its eclecticism incredibly familiar and comfortable, and everything in the house felt reliable and easy to use (bathroom, bedding, shower, shared areas, etc).