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Destination Guide

Chicago is the city that works. The city of big shoulders. Chicago contains North Americas tallest building and one of the worlds largest office buildings. It is a city where the ubiquitous el trains create an almost deafening clatter. The city looks big. Feels big. Is big.

At first glance, it can be overwhelming. But like any city, Chicago is the sum of its parts, and its parts are diverse. Chicago is known as the city of neighborhoods. There are over 75 official neighborhoods in the city, even more if you count the names real estate salespeople have come up with. Each neighborhood has its own distinct quality and character.

So when trying to digest Chicago, don't attempt to take it all in with one big bite. Break it up into manageable portions.

In and Around Downtown

The Loop

This area takes its name from the elevated train, the 'el,? that 'loops? around the citys central core. While the downtown area continually expands beyond these boundaries, much of the life blood that fuels the rest of the city still pumps through the Loop. The Sears Tower, North Americas tallest building is here, as is the Chicago Board of Trade, one of the biggest options and futures trading floors in the world. City government offices are based here, as are the home offices of several major corporations.

When its time for the city that works to relax, the Loop doesn't disappoint. The citys magnificent Harold Washington Library, the Art Institute of Chicago and the Chicago Cultural Center are all here. While not as ritzy as the citys Magnificent Mile, State Street is a shopping mecca, anchored by the flagship stores of Marshall Fields and Carson Pirie Scott and Company. Toys R Us, Old Navy, Filenes Basement and several other chain stores have major outposts on State Street.

Thanks to a burgeoning theater district, the Loop is increasingly becoming a place to be after the workday is ended. The recently restored Ford Center for the Performing Arts-Oriental Theater joins the Shubert Theater and Chicago Theater to form an theater triumvirate where hugely lavish Broadway productions typically play.

Many restaurants, such as The Original Heaven on Seven, Millers Pub, and Berghoff, vie to whet the Loop-goers appetite. Newer 'Boutique Hotels? such as the Hotel Allegro, Hotel Burnham Chicago and Hotel Monaco compete for guests against the more traditional Palmer House and Chicago Hilton Plaza and Towers.

While technically just outside the Loops borders, nearby Grant Park is not to be missed. Hugging Lake Michigan, this park is frequently termed Chicagos front yard. The glitzy Buckingham Fountain is here, as is a plush rose-garden and the Chicago Symphony Orchestras outdoor home, Petrillo Music Shell. The yard is immense, and has the capacity to hold up to 3 million people, as proven by the annual Taste of Chicago festival. Grant Park also plays host to many music and arts festivals during the summer, including Jazz Fest, Blues Fest, and Gospel Fest.

Near North Side

Just to the North of the Loop, bordered by the Chicago River on the South, the Lake on the East and North Avenue on the north, is Chicagos Near North Side neighborhood. This area is in turn made up of several other smaller areas.

The citys "Magnificent Mile" (known as the "Mag Mile" to locals) is one the Near Norths most famous components. Stretching along Michigan Avenue from the Chicago River to Oak Street, this shoppers? paradise is home to high-scale chains like Neiman Marcus and Bloomingdales at the 900 North Michigan Avenue Shops, as well as such lavish boutiques like Marylin Miglin, Candle Court, and Room and Board. The citys monument to modernity, the John Hancock Tower, is here, just a few blocks from the citys links to its past, the Water Tower and the Chicago Water Works, two of the few buildings that survived the great Chicago Fire of 1871.

If you are wondering where the people who can afford to shop at the more expensive stores on Michigan Avenue live, then head east to Streetervile, or the adjoining Gold Coast neighborhoods. Theoretically, the Gold Coast got its name from the African coast of the same name, but the moniker also describes the areas opulence. Indeed, the neighborhood is the nations second wealthiest, surpassed only by New York Citys Central Park East.

Sandwiched between the Mag Mile and the Chicago River is River North, home to an eclectic mix of swank galleries, trendy restaurants (for example, Wolfgang Pucks Spago) and theme restaurants here (for example, The Hard Rock Café and Ed Debvics). While many of the citys residents would like to pretend they have never been to these restaurants, they have--so go and enjoy with a clear conscience.

South Loop

In stark contrast to the garish designs of the theme restaurants, the South Loop offers a quaint, old-world charm, neighborhood bars and smaller restaurants. Once home to one of the largest publishing centers in the Midwest, the warehouses left behind have been renovated and taken over by young, affluent professionals who wish to walk to work in the Loop. The areas focal point, Dearborn Station, sets the tone for the neighborhood. Once a rail transportation hub, this buildings façade has been lavishly restored.

Beyond Downtown

Hugging the lakefront is Lake Shore Drive, one of the citys major north-south arteries. While the Drive will take you to many of the citys attractions, don't forget that this boulevard is an attraction itself. The lake view, the bold skyline and even the drives own tree-lined medians offer some of the best sights in the city.

But having said this, Chicagoans get in their cars to drive and have little patience for Sunday drivers who gawk at the sites. So when you get on Lake Shore Drive, make sure you have a destination in mind.

Lincoln Park

Coincidentally enough, driving north on the Drive will bring you to the citys North Side, and once you pass North Avenue, you'll quickly be in Lincoln Park, one of the citys more gentrified areas. Tree-lined Fullerton Boulevard with its brownstones converted into condos will give you a feel for the people who live here. Cruising down Broadway Avenue, Lincoln Avenue and Clark Street with the many Gaps, Urban Outfitters, Starbucks and the increasingly rare independent boutique shops will give you an idea of how the predominantly yuppie residents of this neighborhood spend their money.

Lincoln Park also abuts and runs into the DePaul University neighborhood. As such, a variety of bars, dance spots, and inexpensive restaurants in Lincoln Park cater to the college and just-out-of-college crowd.

Not all of Lincoln Park is hustle and bustle. In fact, the park the neighborhood takes its name from is one of the citys largest and most bucolic.

Designed by Frederick Law Olmstead, who designed New Yorks Central Park, Lincoln Park encompasses over 1,000 acres. It contains a zoo, a conservatory, a pleasant tarn and several paths connecting it to lakefront beaches. Pickup games of soccer and ultimate frisbee abound on warm summer days.


Heading farther north will bring you to Lakeview, a neighborhood that serves as a popular nightlife center for both the straight and gay and lesbian communities. For better or worse, these groups tend to party separately, with the standout exception being Berlin, a late-night dance club where hipsters of all orientations party together.

Halsted Street between Belmont Avenue and Addison Street serves as the headquarters for nightlife for the gay and lesbian community. The area isn't hard to find -- just look for the gigantic rainbow-colored pylons that dot the sidewalks. Stop in at Sidetrack Video Bar to start the night. For dancing, head to Roscoes Tavern or to Spin.

If partying isn't your thing, don't despair, the area also offers its share of restaurants, from Ann Sathers and Nookies Tree to the 24-hour Melrose Restaurant.

For the straight set, head a few blocks west to Wrigleyville, a bar area that gets its name from nearby Wrigley Field, home of the Chicago Cubs baseball team. The numerous taverns here make for excellent bar-hopping, so stop in Hi-Tops, the Cubby Bear and The Metro, a bar that features live music and up-and-coming rock bands like the Smashing Pumpkins, who played here before they made it big.


For more live music head farther north, where you'll find the Aragon Ballroom, The Riviera and the prohibition-era jazz bar, The Green Mill. When you're strolling through this area, an unfortunate word of caution is in order. As the once-grand, now deteriorating buildings that house the Aragon and the Riviera suggest, this once-posh neighborhood has changed drastically in the last 20 years. Still, some of the best music in the city -- be it jazz, rock, or something in between -- can be found here.

Wicker Park/Bucktown

Yet another hot spot for artisans and heavy drinkers alike is the Wicker Park/Bucktown area. Hang out at bars like the Blue Note, Holiday Club and Mad Bar or restaurants like Northside Café, Zoom Kitchen or Beat Kitchen, and it won't be long before some hipster starts talking to you about gentrification, how the 'evil yuppies? are starting to move into the area and will soon ruin the neighborhood.

Gentrification is a part of life in a living city like Chicago. Twenty years ago, the now-gentrified Lincoln Park was like Wicker Park is today. So, if in another 20 years, Wicker Park follows suit, the hipster will have long since moved on to create another trendy neighborhood.

For the time being however, gentrification in Wicker Park is a four-letter word. Enjoy the diversity of this area while it lasts.

The South Side

If you're visiting the city, don't make the mistake many North Siders do by forgetting that Lake Shore Drive also runs south of downtown.

As you cruise south on Lake Shore Drive, observe the newly-created Museum Campus where the Shedd Aquarium, Adler Planetarium and the Field Museum converge. If you have the time, you could easily spend a day in each museum (see Recommended Tours.) but its also well worth a stop just to enjoy the lake views and watch sailboats go by.

Further south, you'll pass by Soldier Field, home of the Chicago Bears football team?at least for now. The Bears and city officials are deadlocked on whether to renovate the 73-year old stadium or to build a new one at a yet-to-be-decided site.

Immediately after gawking at Soldier Field you'll have to guard against whiplash as you turn to stare at the gargantuan McCormick Place. As big as this convention center is, it seems like every other year they are adding on to it, and during the year when construction is dormant they are talking about adding on to it.

Further south, the charming Hyde Park neighborhood has a quaint, old-world look to it. Home to the world-famous University of Chicago, the area boasts interesting restaurants like the Dixie Kitchen and Medici, great used book stores like O'Gara and Wilsons (the oldest used bookstore in the country), and the quaint 57th Street Art Fair. Hyde Park is also home to the gigantic 350,000 square-foot Museum of Science and Industry. This monument to 20th century technology houses a replica coal mine, a German U-Boat and a Zephyr train all under one roof.

But after visiting the museum, push away thoughts of industriousness long enough to take a leisurely stroll through Jackson Park. Like its sister, Lincoln Park, to the North, Jackson Park was designed by Frederick Law Olmstead. It features a Japanese Garden, a bird sanctuary and a reflecting pond.

So don't be overwhelmed by Chicagos size or grit. Just find a corner of this city that suits you and celebrate its diversity.

David Plowman