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.
6. Pack mindfully. The seasonal range in Chicago runs from bone-chilling winters to sweltering summers. Other than maybe the mildest of transitional spring and fall days, packing for Chicago is not a no-brainer. In winter, hat and boots are a must. Ditto sunhat and sun block in summer. Complicating generalizations, the vast Lake Michigan holds sway over the local climate in ways visitors don't expect, often producing days cooler near the lake in summer and warmer in winter. You can't predict a 60-degree August afternoon, but the best way to plan for it is to pack layers.
7. Show-go. Chicago's renowned for its sports and restaurants and music. But I'd argue the liveliest entertainment quarter is in the theater. Chicago sends hits to Broadway (Steppenwolf Theater's August: Osage County this year) and keeps Broadway playing here indefinitely (Wicked and Jersey Boys will stay as long as demand holds). And it's not just the big stages (Goodman, Court, Chicago Shakespeare, Lookingglass, Victory Gardens, Second City and Steppenwolf), but the little ones – the off-Loop storefront theaters with a coupla dozen seats – where creativity is nurtured as in few other cities. Top choices include Actor's Workshop Theatre, House Theatre, Lifeline Theatre, Profiles Theatre, Redmoon Theater, Steep Theatre, Timelineand dozens of others whose artistic directors will now flame me for not including them.
8. Plan ahead. Anything worth doing in Chicago is worth booking ahead. That goes for hot tables – give Alinea and Charlie Trotter's a call a month in advance of your visit; others like Blackbird and Sepia aren't as punishing but reservations are an unspoken essential, especially on weekends. This advice also applies to popular activities such as the Chicago Architecture Foundation's architectural boat tours, which allow you to book ahead (tip: avoid Sunday post-hotel-checkout noon-hour tours in summer which are the Foundation says are the most crowded). Even the Field Museum and the Museum of Science and Industry allow you to pre-order tickets online, which can save you the aggravation of standing on line with the crowds.
9. Ask directions. Downtown Chicago is laid out on a grid, with the epicenter being Madison St., which runs east-west, and State St., which runs north-south. Street numbers then escalate in any direction 100 per block (10 N. State St., for example, would be on the block just north of Madison, 300 S. Dearborn would be three blocks south of Madison, and 215 W. Randolph St. would be two blocks west of State). Still confused? Ask a local. Chances are if you stand on a street corner with a map and a perplexed look someone will offer their help. It's that kinda town, Chicago is.
10. The great urban outdoors. Now that I've made a great argument for culture and dining, let me switch tracks and recommend that you spend at least part of your time in Chicago recreating. One of the things that makes Chicago such a livable city is its parks, beaches and its all-around regard for the outdoors. Many of my Chicago friends won't take vacations in summer because they consider it so perfect here then (these are the folks you meet in the Caribbean in February). Hit the lakefront and rent bikes or skates, take a walk, watch birds (fall and spring are particularly good for migrating birds along the Lake Michigan flyway), swim or join a sand volleyball game at North Avenue Beach (the last two are summer only, of course). Even in winter the ice shard stacks along Lake Michigan make pretty scenery, provided you're well-bundled.
Elaine Glusac is the author of USA TODAY's Chicago City Guide