Chicago: What to See and What to Skip

PHOTO: Tourists admire The Cloud Gate, also called the Bean, sculpture in Millennium Park in Chicago.Getty Images
Tourists admire The Cloud Gate, also called the "Bean," sculpture in Millennium Park in Chicago.

My kind of town? Absolutely. Chicago can be a traveler's paradise, with world-class restaurants and bars, music venues and theaters, museums and attractions all within a short stroll from your hotel. But Chicago is, itself, a city of trekkers, with thousands of people traveling from their suburban homes into the heart of the city every day. The Windy City, therefore, might be best defined by venues and attractions well off the beaten path. Here are a few ideas.

See the 'Hoods, Skip the Loop

For tourists, the famous Chicago Loop is the heart of the action: great hotels, great restaurants, great entertainment. But any local will tell you that where a genuine taste of Chicago thrives is in the many unique neighborhoods that radiate out from Chicago's downtown.

Take Pilsen, a neighborhood founded by Eastern Europeans in the late 1800s that is now home to a wonderful enclave of residents of Mexican, if not Hispanic, descent. Richly colorful murals abound, as do authentic eateries and shops, especially along 18th Street. Pilsen is on the National Registry of Historic Places and is home to the must-see National Museum of Mexican Art and the must-visit "2nd Friday Gallery Night," a monthly community event that sees local artists throw open their studio doors.

Of course, more than 75 other wonderful Chicago communities abound, including Lincoln Square to the city's north, home to German bars, approachable restaurants and the great Old Town School of Folk Music, and Lake View, where Boystown, Wrigley Field and the shores of Lake Michigan are all within walking distance.

Ride the 'L,' Skip the Tour

Organized tours can be a great way to learn the ins and outs of an amazing city like Chicago. But the "L," Chicago's rapid transit system, provides eight lines for you to explore the city, and its 'burbs, on your own. The routes are color-themed; the Brown Line takes you into Chicago from the eclectic Albany Park neighborhood, with some dramatic city views as you ride in, while the Blue Line runs 24 hours and is a traffic-free and cheap way to get from O'Hare to downtown. If you visit during the holidays, look out for the festively festooned Holiday Train, which travels all the rail lines carrying (who else?) Santa.

Taste the Dog, Skip the Pizza

Did he really just suggest skipping the pizza, that classic deep-dish taste of Chicago? Of course not. Even thin-crust fanatics owe themselves a taste. But be sure to seek out the Chicago-style hot dog, too. The all-beef frankfurter is steamed to perfection before being stuffed into a fluffy bun and crowned with yellow mustard and a bevy of toppings, from white onions to pickled peppers to tomato slices. What a meal. Some of Chicago's vendors are as popular with locals as the wieners they sell, including Hot Doug's in Avondale and The Wiener's Circle in Lincoln Park.

Shop Lincoln Park, Skip Michigan Avenue

The shopping along Michigan Avenue is nothing short of legendary. But avid shoppers owe it to themselves to open their wallets along Armitage Avenue, Halsted Street and Webster Avenue in the Lincoln Park neighborhood. Dozens of shops cater to lovers of all things clothing, cosmetics, handbags, home d├ęcor, shoes, stationery and lingerie. Take a break and sip the daily drink specials at Kincade's. And enjoy the view: tree-lined streets and Victorian row houses make for a pretty setting.

Walk the Pedway, Skip the Sidewalk

The Pedway will come in especially handy especially during winter, when the wind and the chill can make walking the Loop above ground a feat for the brave, or the numb. This network of tunnels covers about 40 city blocks and connects several hotels, like Swissotel and the Fairmont, to skyscrapers, stores and train stops. Artist Hui-Min Tsen is known for leading free Pedway tours; the 2-mile trudge takes 90 minutes.

Ride the River, Skip the Cab

For a unique vantage point of the city while getting from Point A to Point B, ride a water taxi along the Chicago River. This is a seasonal service, running a closed loop spring through autumn from Chinatown to Madison Avenue, but a special way to navigate the city and avoid street congestion. Chicago Water Taxi is operated by the famous Wendella Sightseeing Co., which, along with several other great boat and kayak companies, also provides wonderful architectural tours along the water.

See the Flatiron, Skip the Art Institute

The cultural weather at the Art Institute of Chicago is breathtaking. But the Flatiron Arts Building is a sight to behold, with 88,000 square feet of space in Wicker Park that allows artists and musicians to live in the very studios in which they create. This artists' colony, housed inside a building that is, itself, an architectural marvel, has been around since the 1980s. And artists regularly welcome visitors, like painter Hiromi Tanaka in Studio 205 and tile-maker Karen Gagich in Studio 339.

Watch from Hancock, Skip the Skydeck

There's no denying the drama that the views from the Willis Tower's Skydeck have to offer; you're on the 103rd floor of the world's third-tallest building, after all, and those glass boxes jet out more than 4 feet from the ledge. But you can avoid the crowds by checking out the sweeping visuals from the Observatory at the John Hancock Center across town; the 360-degree outlook from 1,000 feet up allows you to catch glimpses of four states and, every January through March, a 900-square-foot ice rink opens its doors.

Also at the Hancock: the Signature Room on the 95th floor, where you can catch the sights while sipping a stiff one. And speaking of views: consider the seven-minute ride on the Ferris Wheel at the Navy Pier, which sweeps you 150 feet above the ground over and over.

Gabe Saglie is senior editor for Travelzoo. For information about Chicago hotels and attractions, check out this site for destinations, this one for great deals, and this one for hotels.