In Chicago, the true insiders are those who stay out of the loop
Conventions keep the central windy city hotels busy and expensive, so get the heck out of the business district.
Seneca Hotel & Suites occupies prime real estate: diagonally across from the high-end Water Tower shops and next to the landmark Hancock Tower. It has a 24-hour fitness center and three restaurants. And there's an employee whose sole job is to polish the extensive brass fittings. So why is this apartment hotel one of the least expensive places to stay in the neighborhood? Maybe because it's still somewhat unknown. The 17-floor building splits space between permanent residents--who pay up to $4,000 a month to live here in high style--and other guests, who rent spacious, fully equipped mini-residences by the night or the week. The rooms have no view to speak of, but they're stocked with cable TV, a dining area, a spa tub, and a kitchen with a full-size fridge, microwave, and, luxuriously, a dishwasher.
Reaching for the upscale, the 149-room Talbott Hotel (in the heart of the high-rent Gold Coast, two blocks west of the Seneca) caters to Magnificent Mile shoppers. Although the lobby's plaid wallpaper, fox-hunting bugles, and leather furniture portray an idealized notion of an English hunting lodge, rooms are less hokey, done in soothing crimson and forest green and big enough (360 square feet and up) for a family. The 1927 building contained apartments until 1986, and two years ago it was refitted with comforts such as two-sink bathrooms in granite and marble (with separate shower and bath). The rooms' thick carpets are so plush you could fall asleep on them. There's also free Wi-Fi, and guests are given passes to a gym several blocks north.
Few hotels at the north end of the Mag Mile have a view, but the Tremont Hotel, a block south of the Talbott, is an exception. No neighboring skyscrapers obstruct the sight of Michigan Avenue's shops, a half block away--which makes it easier to forgive the smallish size and lemon-lime color scheme of the 130 rooms. Large marble bathrooms and in-room stereo systems (ask for one) also elevate the Tremont, which is otherwise traditional and predictable. Extra points for former Bears coach Mike Ditka's popular restaurant and cigar lounge connected to the lobby.
As you'd expect in a place that cheerfully supplies free, fresh-baked cookies at the front desk--look for the chocolate-chocolate chip--the staff of the 160-room Claridge Hotel is uncommonly friendly. Rooms are beige in color and in spirit--nothing daring or lush, but comfortable. The oak-trimmed lobby bar is a cozy place to spend a few hours with some brandy on a chilly night, but going out is easy, too: The property is only a block and a half from the restaurants and nightlife of Rush Street, yet it is far enough away to be buffered from its noise. Ask for one of the front rooms, which face the lake.
In the heart of the entertainment trifecta in Lakeview--depending on the direction you take, a 10-minute walk can lead to the restaurants of Broadway, the wine bars and theaters of Halsted Avenue, or the people-watching at Lincoln Park--the four-story Willows Hotel, on a quiet residential street, could get away with charging more for its understated elegance. Beyond the proud, colonnaded lobby, the 55 salmon-and-mint-colored rooms, favored by business travelers who crave cheap but dignified quarters, are bright and appointed with terry-cloth robes. And, as if the hotel isn't enough of a secret, it's said to rest atop underground tunnels once used by former guest Al Capone.
Just up Lake Shore Drive, amid the funky shopping and entertainment on Belmont Avenue (and the Boys' Town gay district), lies the Majestic Hotel. Off the lobby of this onetime girls' prep school dorm, the wood-paneled Oxford Room draws neighbors who drop by for chats over free coffee. Standard rooms are on the small side; request one with a bay window since they're a little bigger. Or go for one of the huge suites, which cost about $25 more but include a microwave/fridge combo adequate for basic meals, and, just off the bedroom, a little sunroom that doubles as a TV area. This is the best choice for Cubbies fans--it's a five-minute walk east from historic Wrigley Field.
Broadcast journalist Andy Shaw, the local ABC station's political reporter, and his wife, Mary, run the old-school B&B known as the Windy City Urban Inn, near Lincoln Park, on the city's north side and within walking distance of the El's red line and the zoo. In sight of historic St. Clement Church, the 118-year-old mansion was converted into five rooms and three apartments, all named after famous Chicago authors (Studs Terkel, Saul Bellow, Gwendolyn Brooks) and filled with city memorabilia. Every room is different, but, interestingly (considering the proprietor's day job), most lack TVs. Guests share the sets in the common rooms, including the Ernest Hemingway lounge, as well as a kitchen. The best rooms are on the third floor: Airy, romantic, and loft-like, they sleep up to four and have skylights and spa tubs.
Heart O' Chicago Motel, in the Edgewater neighborhood, about nine miles north of the Loop, is one of a dying breed of retro motor lodges. The area can be traffic-heavy, mostly because of its main asset: a location within easy driving distance of several universities (Northwestern, DePaul, and Loyola) and the stores and restaurants of Little India. The rooms in this kitschy, two-story motel (circa 1959), reportedly patronized of late--for what it's worth--by members of REO Speedwagon and Blue Man Group, are nothing special (think dandelion-yellow baths and brown bedrooms). But don't let the bare-bones look deter you--free parking is a treasure in these parts, and you'll be close to the lively bar-hopping and shopping scenes around Clark Street and Broadway.
Seneca Hotel 200 E. Chestnut St., 312/787-8900, senecahotel.com, from $99
Willows Hotel 555 W. Surf St., 800/787-3108, cityinns.com, from $139 including breakfast
Talbott Hotel 20 E. Delaware Pl., 800/825-2688, talbotthotel.com, from $159
Tremont Hotel 100 E. Chestnut St., 312/751-1900, tremontchicago.com, from $159
Claridge Hotel 1244 N. Dearborn Pkwy., 800/245-1258, claridgehotel.com, from $139
Majestic Hotel 528 W. Brompton St., 800/727-5108, cityinns.com, from $169
Windy City Urban Inn 607 W. Deming Pl., 877/897-7091, chicago-inn.com, no kids under 10, from $115 including breakfast
Heart O' Chicago Motel 5990 N. Ridge Ave., 773/271-9181, heartochicago.com, from $62