When to Go

June, September, and October are mild and sunny. November through March ranges from crisp to bitter, April and May can fluctuate between cold/soggy and bright/warm, and July and August can be either perfect or the deadly combo of high heat-high humidity. That said, the only thing certain about Chicago's weather, according to locals, is that it will change. If you head to Chicago in warmer months, you'll be able to catch some of the fantastic outdoor festivals; during the holiday season, the city's decked out in lights.

When Not To Go To Chicago

Here are some considerations if you're looking for headache-free travel.

Many leisure travelers are fazed by Chicago's frigid winters and the somewhat rough conditions they can cause (slippery roads, delayed traffic, the very thought of schlepping around in big boots). So, while museums and performances are at their max during winter, it might not be the opportune time to travel stress-free.

Also be aware of the more than 1,000 conventions and trade shows scheduled throughout the year. The National Restaurant Association show in May; the manufacturing technology show in September; the Radiological Society of American show in late November; and the National Housewares Manufacturing show in January are among the biggest. Hotel rooms may be hard to come by -- and tables at popular restaurants even harder.

Contact the Chicago Convention and Tourism Bureau at 877/CHICAGO (877/244-2246) for information on conventions, trade shows, and other travel concerns before you book your trip.

Proximity to McCormick Place, where most of Chicago's huge trade shows hunker down, is often a conventioneer's top priority, so most wind up staying in the Loop or South Loop, where hotels are just a five-minute cab ride away from the mammoth venue. In these neighborhoods, accommodations tend to be older and somewhat less expensive -- although there are certainly a few exceptions. Expect somewhat quiet nights in these parts; while the Loop boasts a revitalized theater district, come sundown, there's a lot more revelry north of the Chicago River in the neighborhoods surrounding the Mag Mile. Vibrant Rush Street is the site of many bars, while River North has a high concentration of restaurants and nightclubs.

A meeting or convention in Rosemont or a tight flight schedule should be the only reasons to consider an airport hotel. Prices at these properties are a bit lower, but the O'Hare area is drab. Plus, trips from there to downtown may take an hour during rush hour, bad weather, or periods of heavy construction on the Kennedy Expressway.