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Best Chicago Hotels

AOL PICK from our Editors
Perhaps because so many conventions take place here, the best Chicago hotels skew toward the luxury and mid-range—a fact that can be frustrating to those of us without an expense account. It’s particularly difficult to stay downtown without blowing the bank. You can expect to cough up north of $175 a night downtown, even for bargain-basement chains. And often, to get the best rate you have to pay in full when making the reservation. Take consolation in the fact that you’re likely to get a pretty nice room. Chicago saw a wave of hotel openings between 2008 and 2010, meaning that if you’re willing to fork over at least $200 a night, it’s easy to find a place with good amenities and good service. Hotel rooms get less pricey the farther you get from the Loop and the Magnificent Mile, but you might end up blowing the difference on cabs, anyway. If you’re not planning to spend a lot of time downtown, or you’re willing to take the "L," consider a hotel on the North Side, where the accommodations are a little cheaper. Some of the best places to stay in Chicago are just a bit off the beaten path. Whatever you do, do not be tempted to stay in one of the North Side motels on North Lincoln Avenue between Foster and Devon, a.k.a. Sin Strip. Their rates are rock-bottom for a reason. Make that several reasons: crime, poor location and rooms that haven’t been renovated since the Carter administration.
Trump International Hotel & Tower

Trump International Hotel & Tower

Neighborhood: Magnificent Mile Price Range: Expensive
How rich do you have to be to stay in a hotel built by Donald Trump? Let’s just say that if you’re not in the habit of lighting your cigarettes with $10 bills, you’ll probably save a stay at this top Chicago hotel for very special occasions. At the Trump—which is poised on the Chicago River just west of North Michigan Avenue—they personalize everything from your mini-bar to your stationery, a bottle of water runs $25 and reservation add-ons include a flight of different gummy bears and a “purifying diamond massage.” Book at least three months ahead of time for the cheapest rooms (ask for a king room with a city view; they start at $395).

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The Peninsula Chicago

Neighborhood: Magnificent Mile Price Range: Expensive
When your hotel sits just across the street from a Neiman Marcus and you can watch television in the bathroom, you know you’re staying in Swanksville. Rooms normally start at $575 and run all the way to $8,000 for the Peninsula Suite at this classic Magnificent Mile luxury hotel, but check for special packages that sometimes include room rates of a mere $410 or so. If you’re staying elsewhere but would like to experience just a taste of Peninsula luxury, book a spa treatment, such as an aromatherapy massage; at $155 for 60 minutes, it’s “only” about $50 more than you’d pay anywhere else in town. Tip: For first-time guests, finding the front desk takes some doing. After you enter the hotel, take the elevator to the sixth floor, walk down the hallway, and you’ll see it.

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Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Neighborhood: Magnificent Mile Price Range: Expensive
The Four Seasons occupies the 32nd through the 46th floors of 900 N. Michigan Ave., above Bloomingdale's and other shopping options. With high-end shops just a step away, this is the place to stay if you’re feeling flush and ready for some retail therapy. Keep your eyes open along with your wallet—Oprah’s longtime boyfriend, Stedman Graham, has been spotted shopping here. Rooms in the hotel do sometimes go as cheap as $295 a night, but that’s if you’re willing to book a three-night stay. Demonstrating that anything can be outsourced if you’re willing to pay for it, the Four Seasons’ services include a butler who will read bedtime stories to your children—perhaps after you dine at the swanky on-site restaurant, Seasons.

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Windy City Urban Inn

Neighborhood: Lincoln Park Price Range: Moderate
If you’d like to get out of downtown without going too far off the beaten path, try this urban bed and breakfast in Lincoln Park. Not only are its rates ($115-$225 for a single or double room; $185-$325 for a coach house apartment with kitchen) cheaper than the downtown hotels, but it lies within a 10-minute walk of the Fullerton Red Line stop and within a 20-minute walk of the free Lincoln Park Zoo, making it a fine choice for budget travelers. Look to inn co-owner Andy Shaw—a retired local television reporter—for the scoop on where to go and what to do during your stay in Chicago.

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House 5863

Neighborhood: Andersonville Price Range: Budget
If you’re neither a huge-impersonal-hotel nor a frilly-bed-and-breakfast type, House 5863 might be for you. Though this Andersonville spot advertises itself as a B&B, it really feels more like a self-service guest house—there are no doilies, no communal breakfast with strangers and, strangely enough, no hosts in sight (though the manager is only a phone call away). Furnishings are modern and attractive, if not lavish, and complimentary beverages are available throughout the day. The location is a major plus if you’re looking for independent shops and restaurants—a few minutes’ walk west and south brings you to Clark Street, where you’ll find many coffee shops, restaurants and adorable little boutiques. Rates for double occupancy start at $99.

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Ohio House Motel

Neighborhood: Downtown Price Range: Budget
If you’re on a tight budget but still absolutely determined to stay downtown, try this no-frills place just west of the Magnificent Mile. The Hilton this is not—rooms are Spartan, and if you need any frills besides a bar of soap, you’ll have to bring them yourself. But it’s safe, decent and within walking distance of public transportation and many downtown attractions. Doubles start at $99 a night, parking and Wi-Fi are free and the retro greasy spoon downstairs is good for cheap, enormous breakfasts.

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J. Ira and Nicki Harris Family Hotel

Neighborhood: Downtown Price Range: Budget
OK, budget travelers—this is as cheap as it gets without resorting to the kind of place that rents by the hour. The second-largest hostel in the United States, it occupies a six-story building in the South Loop and is an easy walk to downtown attractions. If you’re willing to share a basic but clean dorm room with five to nine other people of the same gender, you’ll pay just $32-$38 a night (minus $3 if you’re a Hostelling International member). Unlike many other hostels, there’s no curfew here, and guests have 24-hour access to their rooms. You’ll get a locker to store valuables (bring your own lock), sheets, a pillow, a towel and a satisfying sense of thriftiness.
Days Inn Lincoln Park North

Days Inn Lincoln Park North

Neighborhood: Lincoln Park Price Range: Budget
This Lincoln Park location of the national chain isn’t the most atmospheric place to stay—it might be the former hangout of legendary jazz musician Bix Beiderbecke, but it’s still a Days Inn, with all the beige walls you’d expect. But with doubles starting at $97, and a location within walking distance of the lake, Lincoln Park Zoo and Wrigley Field, who cares? Ask for a courtyard room if you’re noise-sensitive (it’s a busy neighborhood), and if the included breakfast doesn’t fill you up, try the nearby greasy spoon, Golden Nugget Pancake House.

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