Gold Coast Guest House (113 W Elm St, 312-337-0361, bbchicago.com) Housed in a 19th-century Victorian townhouse (built just after the Great Fire ravaged the town), this B&B is a welcome oasis of good-value accommodation in a swanky neighborhood. Sally, the friendly owner, is happy to chat with guests over a glass of wine in the lush garden. Be sure to book ahead, as there are only four guest rooms. Rates start at $129.
House 5863 (5863 N Glenwood Ave, 773-944-5555, house5863.com) From the dark red exterior of this Edgewater B&B, the plasma-screen TV in the lobby and the modern design of the five guest rooms—outfitted in a primarily black-and-white palette with low-to-the-ground furnishings—the place eschews that stale vibe some older B&Bs exude. Relax in the outdoor garden, which can be reserved and catered for any event. Rates start at $99.
House of Two Urns B&B (1239 N Greenview Ave, 773-235-1408, twourns.com) Wicker Park’s reputation as a quirky, artistic enclave fits perfectly with this friendly, offbeat B&B—named after the urn motif found in the stained-glass window and façade of this 1912 brownstone. The Two Urns has nine rooms with eccentric themes such as European antique plates or the tale of The Princess and the Pea. Rates start at $109.
Ray’s Bucktown B&B (2144 N Leavitt St, 773-384-3245, raysbucktownbandb.com) Sitting several worlds away from B&B’s traditionally chintzy image, Ray Reiss’s Bucktown operation is a bed-and-breakfast for the 21st century. The rooms are crisp, fresh and modern, and the facilities are awesome: in addition to Wi-Fi throughout the building, rooms have TiVo-equipped televisions. Rates start at $119.
Wheeler Mansion (2020 S Calumet Ave, 312-945-2020, wheelermansion.com) One of the few mansions to survive the Chicago Fire, the Wheeler is typical of the elegant domiciles that once housed the city’s elite. This 1870 mansion was restored in 1999, turning it into a classy B&B. A five-minute walk from McCormick Place, the 11-room inn is an intimate alternative to conventional lodging. Rates start at $230.
Windy City Urban Inn (607 W Deming Pl, 773-248-7091, windycityinn.com) Extended-stay visitors will find an urban retreat at this Victoria mansion owned by former local TV newsman Andy Shaw and his wife, Mary. Tucked away on a quiet, leafy Lincoln Park Street, the five cozy guest rooms and three apartments (in the neighboring coach house) are inspired by and named after local writers, from Ernest Hemingway to Gwendolyn Brooks. Minimum stay is a month and rates vary.