Five of Chicago's best neighborhoods

Chicago's place on the world stage was set at the Republican National Convention in 1860 when Abraham Lincoln was nominated for the presidency. Since then, it's played a minor role in events such as The Great Fire and The World's Fair, nurtured gangster Al Capone's legacy and ushered in a new era of jazz.

The former Obama stomping ground has counted legends ranging from Oprah to Hugh Hefner to Michael Jordan as marquee residents and holds fast to deep-dish pizza and Chicago-style hot dogs, while embracing its many Michelin-starred scenemakers. Once a mere 1800s transportation hub that connected the eastern and western United States, now it's the third most populous city in the country, behind New York and Los Angeles.

Today's Chicago sits pretty on Lake Michigan and a journey up Lake Shore Drive reveals not only a photogenic waterfront -- deep blue waters, moored boats, a public track for runners and bikers -- but a roster of iconic Chicago strongholds such as Lollapollooza's Grant Park, the Chicago Bears' Soldier Field, Navy Pier and an unforgettable view of the city's skyline.

In many ways, the city is a Midwest melting pot -- Mexican taquerias line Pilsen, Puerto Ricans chill around Humboldt Park and the largest Polish community gathers around Avondale. All told, more than 200 neighborhoods vie for dominance.

With hot and humid summers and below-freezing winters, fall is an ideal time to visit. Here's a look at five of Chicago's best neighborhoods to explore.

THE LOOP

GOOD FOR Sightseeing

A world financial center and media hub, much of Chicago's business is clustered around "The Loop," which extends from the banks of Lake Michigan through the sinewy Chicago Riverfront to essentially cut downtown in half.

The country's tallest building, the Willis (formerly Sears) Tower, is here and visitors can shoot 1,353 feet to the Skydeck on the 103rd floor and take Chicago in from on high ($17 adults, $11 ages 3-11, theskydeck.com).

A walk along State, Wabash, Rush and Clark streets showcases the essence of downtown Chicago: Grassy spaces and parks litter the city grid, offsetting limestone and concrete.

On a clear day, take time to wander Millennium Park. A wonderland of public art exhibits, The Frank Gehry-designed Jay Pritzker Pavillion is the centerpiece offering live music events, while the Crown Fountain, which projects images of locals on two 50-foot screens, can hold unruly kids (and adults) captive for hours (millenniumpark.org).

For Impressionist and post-impressionist aficionados, hit Michigan Avenue's Art Institute of Chicago. The museum has the second-largest collection of art in the country after New York's Metropolitan. Monets abound, but make sure to steal a peek at Edward Hopper's Nighthawks. ($18 adults, free younger than 14, artic.edu).

THE GOLD COAST

GOOD FOR Shopping

Aptly named, the historic Gold Coast district offers some of Chicago's finest real estate for both nesting and shopping. Dotted with doorman-patrolled high-rises, luxury brands such as Chanel, Barneys, Jimmy Choo, Prada and Hermès make their homes along Oak Street, anchoring high-end hotels like the Elysian and The Drake. The adjacent Magnificent Mile (themagnificentmile.com) on Michigan Avenue only ups the ante.

A stroll down leafy Astor Street offers an architectural glimpse of the immaculately kept mansions and greystones of yesteryear. On State Street, the original Playboy Mansion can be ogled from afar.

When you need a retail break, restaurants such as Italian favorite Spiaggia and the reopened Pump Room (a favorite of Frank Sinatra, Dean Martin and Judy Garland) at Ian Schrager's new Public hotel keep the well-to-do well fed (publichotels.com).

Be aware of the "Viagra Triangle," a small park at the intersection of State and Rush streets, a notorious pickup spot. Instead, refuel across the way with some deep-dish sausage pizza at Lou Malnati's. The clubby, subway-tiled space is one of many locations and, contrary to Gold Coast philosophy, will go easy on your wallet ($12 for a small pie, loumalnatis.com).

THE WEST LOOP

GOOD FOR Eating

Home to Oprah Winfrey's Harpo Studios (Rosie O'Donnell's new set), the West Loop was once a mix of meatpacking factories, produce markets, wholesale outlets and the city's oldest building -- Old St. Patrick's Catholic Church.

These days, mixed in are stunning loft condos, boutiques, swank art galleries and a funky vintage market on Randolph Street that features more than 200 furnishing, clothing, jewelry and collectible vendors (randolphstreet market.com). Add to that, restaurants; the West Loop is fast becoming Chicago's gourmand go-to destination.

"Top Chef" winner Stephanie Izard's Girl and the Goat is an unpretentious spot that's always booked, but if you're up for a couple of cocktails, you can wait out a walk-in spot (girlandthegoat.com).

Down the street at the communal Publican, the small plates menu focuses on fish and pork. Start with some oysters ($30 a dozen), and then try the ham tasting ($21, thepublicanrestaurant.com).

You can't talk food in Chicago without mentioning Grant Achatz, the James Beard Award winner behind the highly successful Alinea, and now the West Loop's Next. At Next, each three-month menu is based around a theme (most recently, Thailand), and tickets are sold for nightly seatings (nextrestaurant.com). Impossible to land a coveted ticket? Try for a reservation at Aviary, the Grant Achatz über-cocktail bar next door (theaviary.com).

WRIGLEYVILLE

GOOD FOR Sport

Rising up above residential streets, a motley collection of bars and restaurants ignites into madness as the Chicago Cubs play ball at their home park since 1916. Roars engulf the stadium with each turn of the bat. Although they haven't won a championship in more than 100 years, 40,000-plus fans file inside the stadium to watch one of the country's only hand-turned scoreboards.

For a novel way to watch the game, check out Wrigley Field rooftops, a guide to alternative venues around the stadium that have bleachers, open bars and food for up to 200 people. Expect to spend at least $75 for regular-season games -- and book early (wrigleyrooftops.com).

BUCKTOWN/WICKER PARK

GOOD FOR Chilling out

It's hard to tell where Bucktown ends and Wicker Park begins. A cross between Greenwich Village and Williamsburg, these artsy neighborhoods are buzzing with pedestrians, cafes, bookstores and record shops, which makes for great people-watching.

BYOB sushi bars alternate with tequila lounges and health food stores. Yoga centers abound. The community hosts events such as the late summer Bucktown Arts Fest to help artists and micro-galleries gain exposure.

On the weekend, the young and hip are wolfing tacos ($3) and Coronas at Big Star (bigstarchicago.com) on Damen while Wicker Park, itself, is in full swirl. The baseball diamond plays host to a local game, children's groups form near the playground and couples canoodle in tree-lined nooks that overlook a neighborhood of two- and three-story brick row houses with gated porches.

On Milwaukee or Division streets, sit at one of the many sidewalk cafes such as Milk and Honey for a chat (milkandhoneycafe.com) or grab a late afternoon cocktail at Bangers & Lace (bangersandlacechicago.com). For serious grub, it's all about Schwa, a comfort food joint with a twist that's anything but regular ($110 for a nine-course tasting menu, schwarestaurant.com).

IF YOU GO

BY AIR Several airlines fly nonstop between New York City airports and Chicago O'Hare. Southwest operates nonstop flights between Long Island MacArthur airport and Chicago's Midway airports. Trips take about 2 1/2 hours.

GETTING AROUND The city's "El" train can be used to get from place to place within the city. Buses and taxis are affordable and readily available. A car rental is an expensive nuisance.