First, the neighborhood if you're hesitant about staying outside the Loop.
The Bucktown/Wicker Park neighborhood is great---lots of restaurants and architecturally interesting (both old and new) two and three story multifamily homes. You can't beat the location: We had activities in North Side neighborhoods, and we found it both fast and convenient to take the bus down the main drags of Damen and Western, and along North Street returning from Oak Park (as opposed to taking the train through the Loop).
We're walkers and didn't mind the short, six-block walk from the Western or Damen blue-line stations---but it was October, not February. But even if it was winter, it's just about two long blocks from the buses on Western and Damen. Also within short walking distance is the marvelous Margie's (which has AMAZING and inexpensive ice cream sundaes) and an Aldi's supermarket, owned by the same folks who own Trader Joes, with an eclectic selection of groceries. There's also a 24-hour drugstore near the Western train station.
Ray or his staff can generally pick you up at the train station coming in from O'Hare. They considerately phoned us the morning we left headed for Chicago to let us know they were unable to, but it was no problem walking from the Western station to Ray's in a strange neighborhood at night.
In short, although Western Ave. isn't the same kind of upscale neighborhood that Damen Ave. is, it's a pretty safe neighborhood. I wish we had had more time to explore Bucktown, Wicker Park, and the nearby Ukrainian Village (not really a village, just a neighborhood).
Ray has different kinds of rooms. We chose one of his less expensive rooms ($119 plus tax) in a building across the street from the main B&B. It shared a bathroom with another room, and also shared a kitchen and large living room. We were grateful for the fridge and the ability to make tea whenever we wanted. The couple in the other room in this apartment used the living room during the day to entertain their family who lives in Chicago. We didn't trip over each other at all, and both couples managed the single bathroom OK.
Our room had a TV with a zillion cable stations (as did the living room), a large closet, and a space heater, just in case we needed it. (We didn't. The main heating was just fine, and the thermostat was in the living room.) My partner complained that she could hear it when someone took a shower, but it sounded like white noise to me.
On the other hand, I spent an uncomfortable first night in the too-soft bed with feather pillows I didn't like. But Ray very quickly gave us non-feather pillows when we asked about it the next day, and he removed an extra mattress pad, which made the mattress a bit more tolerable. Our room was narrow, so one side of the king bed was against the wall. This isn't the room if both parts of the couple have difficulties getting in and out of the bed, but it was fine for us (I'm in my late 50s and my partner's in her late 40s.)
Ray provides a lot of amenities, from loaner umbrellas, to use of an iMac and printer, to his shuttle to the train station, to late-night snacks, to an absolutely terrific breakfast with choices of cereal, or made-to-order omelets and French toast. He has a wealth of tourist books and pamphlets, and of course he and his staff are available as well.
He also seems to attract a wonderful mix of guests. We had wonderful breakfast conversations with folks from around the country.
In short, if we return to Chicago, I wouldn't hesitate to stay at Ray's again.
