Prices and quality vary neighborhood by neighborhood. If an area seems unsafe, it probably is. Many on-line hotel search engines allow you to view previous guest's reviews so you may ascertain a pleasant stay.
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If you are interested in living the high life, the Conrad Chicago may be for you. Sleek and urban, the hotel features 500-thread count Italian linens, Bose surround-sound stereo, and a 42in plasma TV. The Drake is another high-end option. This hotel offer regal majesty and has hosted such royalty as Queen Elizabeth since opening in 1920. The very quiet rooms are built like bank vaults, with heavy old doors and marble baths. The Fairmont Hotel is another excellent selection. All 687 luxury rooms and suites here are as close to the statues and fountains of Millennium Park as you can stay. Upgrade above a standard room to get a park or lake view (those near the top of the hotel's 45 stories are the best).
For more economical accommodations, there are several nice hotels. Chicago's Essex Inn offers all the necessities and is close to the Museum Campus and Grant Park. A number of the basic rooms have nice views of Grant Park, and facilities include a rooftop pool with a partly retractable roof. Prices edge a bit higher on weekends the Bears are in town. To save money AND see the sights, it might be in your best interest to look at package deals. For some offers from the city of Chicago: http://reservations.choosechicago.com or check out http://www.chicagotraveler.com/hotel-specials.htm.
For a more intimate experience, a B&B might be the perfect answer.
The Gold Coast Guest House B&B is a 1873 three-flat B&B close to shopping and Oak St Beach. The gargantuan floor-to-ceiling windows and spiral staircase are reminiscent of another time in the wealthy neighborhood of the Gold Coast. Each room includes a private bath, individual air-conditioning controls, DVD and CD player, private phone line and free wireless internet access. Guests receive a continental breakfast with sodas and snacks in the fridge at all times. The walled-in ivy-filled garden makes a pleasant escape from the city. The innkeeper - a former London-based travel guide - provides personalized advice, maps and other tools to get you acclimatized. A two- or three-night minimum stay may be required, depending on availability.
Windy City Urbane Inn also offers Victorian home moments from the lake. Each bedroom is named after a Chicago author and Chicago enthusiasm is in abundance.
The Flemish House of Chicago is another option offering furnished studio and one-bedroom apartments in an 1890s greystone row house. The apartments are available for short-term stays (two-night minimum mid-week; three-night minimum weekends) or as furnished corporate units by the week or month.
For a search of all Chicago Bed & breakfast, search on http://www.bedandbreakfast.com/chicago-illinois.html.