Any quibbles? The mattress on one of the beds in my room sagged, but the one on the second bed, with cotton/poly sheets, was firm. There were no luxury toiletries, but there was Dial soap and a bottle of inexpensive shampoo. Since the Flemish House lacks a communal area for breakfast, I also missed the chance to interact with other guests. That doesn't bother travelers like Marilyn Levy of San Francisco, who, with her husband, David, has stayed in five of the seven rooms at the Flemish House over the past ten years. "Heaven forbid I have to face strangers in the morning," she said. "And I don't have to wait for my breakfast" (312-664-9981; chicagobandb.com; doubles, $155–$225).

My next stop in Chicago: Hansen House Mansion, in the prestigious Lincoln Park section, a short walk to Old Town, attractive restaurants, and shops. In this five-story house built in 1886, it's easy to meet other guests thanks to a common kitchen stocked with coffee and biscotti, and a Victorian living room that invites conversation. Innkeeper Fran Ramer, who has an MBA from the Wharton School of Finance and an affinity for antiques, clearly enjoys playing hostess and chatting about her historic real estate. "Hotel guests want anonymity, but mine want something more intimate," she said, describing her total immersion in providing that experience. She carries luggage by herself up the stairs, which she "negotiates with shopping bags" by emptying the suitcases into bags a few times. "I wear all the hats," she continued. "I get tickets, I make arrangements for excursions—and I clean."

If you're there on a Saturday and pay $20 in advance, you can dine on breakfast served on bone china and with crystal stemware while sitting at a Queen Anne table. On my particular Saturday, Ramer swept into the dining room in a long skirt and bearing a tray of fresh-squeezed orange juice, goat cheese and spinach quiche, apple-chicken sausage, pumpkin bread, grapes, and organic baby greens.

Pouring coffee, she talked about the history of Hansen House and its "many hundreds of antiques," including the original Steuben glass lights. A Norwegian architect, Harald Hansen, built the house for his family; today, he and his relatives stare at strangers through gilded framed photos hung liberally over the velvet sofa and along the stairways. I stayed in Hansen's own bedroom, sleeping on a comfortable queen-size bed near a stained glass window made by Giannini & Hilgart, a Chicago firm that also did work for Frank Lloyd Wright. My spacious room had a marble sink, a rococo writing desk, a carved walnut fireplace, a love seat, a walk-in closet, and a nineteenth-century armoire that hid a TV and a DVD player; the adjoining private bathroom, with a marble floor, housed a European hand shower resting on a six-foot-long, two-foot-deep claw-foot bathtub. Sharing space in a tray over the tub were Emile Zola's Nana in paperback (with a bather luxuriating in a claw-foot tub on the cover), a yellow rubber duck, and Ramer's own handmade bath salts.