June - September
Summer is the time when most visitors flock to Chicago—despite the hot and sticky temperatures, which can reach the upper-90s—so don’t count on scoring any hotel deals then. From June to September, the city is chockablock with outdoor festivals of one kind or another; one of the most popular is Taste of Chicago, which takes place downtown in late June and early July and draws shoulder-to-shoulder crowds. The beaches can get crowded during this time, too. That said, if you like the outdoors and don’t mind hordes, the festival scene can be pretty fun, and you can make up for the money you’re not saving on your hotel room by taking advantage of the many free summertime concerts the city holds in Grant Park. Make your hotel and restaurant reservations at least a month in advance and try to plan your visit to avoid any major conventions (contact the Chicago Convention and Tourism Bureau for a convention schedule: 877/CHICAGO).
December - March
Non-locals think that winter in Chicago is a perpetual snowpocalypse with daily sub-zero temperatures and wind that will blow your hair off. Okay, so it’s not warm, but winter is still a great time to visit, especially if you’re crowd-phobic and/or plan to visit a lot of nice, toasty museums, all of which stay open year-round (albeit with slightly shorter hours in the winter). Plus there are several outdoor special events worth bundling up for, like the Christkindlmarket (a large German-themed Christmas fair held throughout December). Look for hotel deals in January and February especially, when room prices can fall by almost 50%. Vital tip: Pack a hat. Without one, it’s all but impossible to stay warm in Chicago’s winter winds, even if the rest of you is well-bundled.
April - May; October - November
Spring and autumn are fine times to visit Chicago if you don’t mind unpredictable weather. Here, even some late-spring days can be chilly enough for a sweater, and late autumn can be hot enough for shorts. You’ll pay a little less for a hotel room in these seasons, but don’t expect rock-bottom deals. The beaches won’t be open, but virtually all other attractions will be, and crowds will be much more manageable than they are in the height of summer. If you’re visiting in spring, be sure to bring an umbrella; Chicago seems to get more than its fair share of rain then.