Chicago Hotels

Even so, it's wise to shop around. Focus on a neighborhood of interest, such as the Michigan Avenue area, also called Near North, and you'll find budget chains like Embassy Suites and luxury properties like the Four Seasons Hotel Chicago within a few blocks of each other.

Or ask yourself if you'd rather be surrounded by Manolo-wearing old money—think Trump Hotel—or tattooed hipsters à la the James Hotel. Is it romance you're seeking—visit the Dana or Hotel Sax—or a weekend with the kids in tow so they can splash around the pool at the Sheraton Chicago Hotel and Towers?

On the lower end, expect well-maintained yet boxy and sparsely decorated rooms. The good news is that free Wi-Fi is now a feature of most budget-friendly hotels, like the Best Western and Holiday Inn chains, or local outfits like the Essex Inn.

Top-tier hotels have no problem filling their rooms: in some cases, this has little to do with amenities. Instead, their vibrant bar scenes are the draw, as is the case at the W Chicago Lakeshore, W Chicago-City Center, the Wit, and the James Hotel. Rooms at these hot spots usually don't go for under $250, but the "it" factor is huge, with attractive crowds queuing at the bar and lounging in the restaurants.

Looking forward, Ian Schrager, who co-founded Studio 54, has announced his plans to partner with Marriott International Inc. to open a new boutique hotel called "Edition" just off the Magnificent Mile.