Whether you're coming to Chicago for the first time or you're a veteran visitor, take heed of the following tips to make the most of your trip.
1. Take the el. It's not only picturesque — as those lumbering elevated mass transit trains ring the Loop at second-story height — it's convenient, and cheap too. Three el or L lines are especially important to consider. From a transportation point of view the Orange Line and the Blue Line link downtown with Midway and O'Hare International Airports, respectively. For sightseeing, loop the Loop aboard the Brown Line, ride it over the Chicago River (digital camera alert: great bridge views) and as far north as you have time for, peering into the backyards, patios and porches en route. Overhead stairways cross the tracks and allow you to return without paying the fare twice. For train buffs, voyeurs, nostalgics or anyone who needs to get off their feet, the el is a great tour.
2. Mind the seasons, but don't let them stop you. Chicagoans regard February as the telling month, the one that keeps the wimps from moving to town for our glorious springs, summers and falls. But life in the heart of winter darkness goes on in every other way unchanged. Bad weather also means good deals at hotels, open tables at restaurants, better theater tickets and cheaper flights to town. Pack for it and consider an offseason trip.
3. Get out into the neighborhoods. The city officially lists 198 neighborhoods. In practice there are thousands of mini-communities around town that make Chicago dynamic. Downtown may employ many of them, but the outlying corner taverns, street-front shops and local restaurants are where they live. From gentrified-bohemian (Andersonville, Wicker Park, Bucktown) to ethnic pockets where English is a second language (Devon Avenue, Chinatown, Argyle Street), there is a great variety from which to experience a lively day the local way. For a guided outing, check out the city-sponsored Chicago Neighborhood Tours.
4. Beware Navy Pier. Navy Pier, the former shipping-dock-turned-amusement-pier is the biggest tourist attraction in the city, drawing 8.6 million visitors annually. That's 5.6 million more than its closest competitor, the Lincoln Park Zoo. So while I wouldn't advise any visitor to avoid Navy Pier, you should know what you're getting into: crowds, of course. But also lots and lots of families, especially in summer and during school breaks, so if you don't like kids, go somewhere else. Finally, it's very expensive, from the parking (rarely less than $20) to the food (which, compounding the price problem, is not very good). But there are ways to enjoy the Pier and avoid the crunch: take the free trolley or go early in the day or early in the week.
5. Bring the kids. Chicago's biggest attractions – Navy Pier, Lincoln Park Zoo, Shedd Aquarium, Field Museum, Museum of Science and Industry, Alder Planetarium — are truly all-ages friendly. Even the Art Institute of Chicago offers innovative kid's tours. Combine the sights with el train and boat rides, Lake Michigan beaches, romps in the Millennium Park Crown Fountain and warm-hearted Midwestern hospitality and there's nothing to prevent a child from enjoying the best of the city.