Chicago hotel rates are as temperamental as the city's climate. And just as snow in April and 70-degree weather in November are not uncommon, it is widely accepted that a hotel's room rates may drop $50 to $100 overnight—and rise again the next day. It all depends on the season and what festivals, conferences, and other events are happening around town. Even so, it's wise to shop around.
Focus on a neighborhood of interest, such as the Magnificent Mile area and the rest of the Near North side, and you'll find budget chains such as Embassy Suites and luxury properties such as the Four Seasons Hotel Chicago within a few blocks of each other.
Or ask yourself whether you'd rather be surrounded by the sedately dressed—think Trump International Hotel—or tattooed hipsters, à la the James Chicago. Is it romance you're seeking—try the Dana—or a quick weekend escape with the kids in tow (they can splash around the pool at the Radisson Blu, then walk a block to Millennium Park)?
On the lower end, expect well-maintained, but often boxy and sparsely decorated rooms. The good news is that free Wi-Fi is now a feature of most budget-friendly hotels, such as the Best Western and Holiday Inn chains, or local outfits such as 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, theWit, and the James Hotel. Rooms at these hot spots usually don't go for less than $250, but the "it" factor is huge, with attractive crowds queuing at the bar and lounging in the restaurants. That said, the roughly 1,500 new hotel rooms that came on the scene in 2013 may help lower prices and increase quality, though it's too early to tell for sure.