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Superstar Cities: New York & Chicago

Premiere art museums, hot jazz, lofty skyscrapers, urban rivers, and snowy winters. With this description, two cities spring to mind: New York City and Chicago. These powerhouse cities have a lot in common, including a soaring architectural landscape and an illustrious art and music legacy that continues to this day. Looking to explore America's cultural history? Plan a trip itinerary that ties in both cities.

The largest museum in the country? The Metropolitan Museum of Art in New York City. The second largest? The Art Institute of Chicago. In museum size alone, the two cities are close rivals—but they also share a similar artistic vision. Both cities foster a dynamic arts community—from the massive museums to boutique art galleries to annual arts shows.

Art Institute of Chicago

Photo courtesy of Choose Chicago

The Art Institute of Chicago, founded in 1866 by a group of artists, not only delves into the city's artistic past but also guides the city's artistic future. Its school (SAIC) is one of the country's best, with notable alumni including Georgia O'Keefe, Edward Gorey, Jeff Koons, and Ed Paschke, among many others.

You could easily spend an entire week or more hopping between Chicago's art museums: Other top spots include the Museum of Contemporary Art, featuring one of the largest collections of modern art in the United States; the DuSable Museum of African American History, with expansive exhibits of African-American art; and the National Museum of Mexican Art, the first Mexican museum in the Midwest.

Museum of Modern Art

Photo courtesy of NYC & Company

In New York City, the Met is, of course, unmissable. But for contemporary art fans, so is the magnificent Museum of Modern Art, which has a double draw: The world's largest collection of modern art and sculpture and a unique and sleek building by architect Yoshio Taniguchi, which is a work of contemporary art in itself. The museum is free on Friday afternoons, and the bonus is that this also includes screenings of indie international films.

Other stellar contemporary art museums are the Frank Lloyd-Wright–designed Guggenheim—located on the so-called Museum Mile—look for the excellent collection of Vasily Kandinsky paintings—and the Whitney Museum of American Art, which hosts the Whitney Biennial, one of the most critically acclaimed shows in the art world, with a focus on up-and-coming American artists.

All that Jazz

Green Mill

Jazz was born in Chicago and the American South, and reached its zenith in 1920s New York. This rich jazz history lives on today in both cities, which have numerous low-lit jazz lounges and clubs where you can tap your toes to established and emerging jazz musicians.

In Chicago, head to the innovative Constellation jazz and performing arts center. Founded in 2013 by Chicago drummer and composer Mike Reed, Constellation is housed in the city's former Viaduct Theatre. For jazz concert–listings throughout the city, check out the Chicago Reader or head down to the South Side, where you'll find a variety of classic jazz joints, or Uptown to the venerable Green Mill, believed to be the oldest continuously running jazz club in the United States.

New York City also has a new jazz club that lives in a famous old space: Minton's, described as "a jazz legend reborn," reopened in 2013 in the former Minton's Playhouse, which dates back to 1938 and hosted everyone from Charlie Parker to Dizzy Gillespie. The new Minton's received a lavish makeover, and you can now sink into plush banquettes and enjoy lively jazz while tucking into high-brow Southern cuisine, from oyster caviar to juicy venison. In the mood for another night (or five) of jazz? Check out the Village Voice for jazz listings, including intimate supper clubs and larger concerts across the city, from Harlem to the West Village.

A River Runs Through It

River Boat

Photo courtesy of Choose Chicago

Chicago and New York City are indisputably the country's top skyscraper cities. Chicago's Home Insurance Building, built in 1885, is considered the world's first skyscraper, and since then both cities have matched each other in soaring heights: The tallest building in the United States (and the Western Hemisphere) is New York City's World Trade Center (rising to an iconic 1,776 feet), and the number two spot goes to Chicago's Willis Tower (formerly the Sears Tower) at 1,451 feet. Though both cities are dominated by a concrete jungle of buildings, they also offer something else: nature. The two cities have mighty rivers—the Chicago River, and the Hudson and East Rivers in New York—which afford plenty of breezy parkland on their banks, along with multiple outdoor activities, from kayaking to sightseeing cruises.

Wine and Dine

Pizza

Photo courtesy of Choose Chicago

Achiote-seared shrimp with habanero pickled onions; Lamb 86—that's lamb with 86 different ingredients, from rhubarb to garlic; grilled quail with smoked pork fat. Peer into restaurant kitchens across the two cities and you'll see chefs charting new culinary territory.

In Chicago, feast at Rick Bayless' Frontera Grill for some of that achiote shrimp and other dishes that reimagine Mexican cuisine. At Grant Achatz's three-Michelin-star Alinea you'll find seasonal fare that combines science and art, like a balloon made from dehydrated apple and filled with helium, and, of course, that ingredient-heavy lamb. At Stephanie Izard's self-described "rustic and bad-ass" Girl & the Goat, try farm-to-fork cuisine such as escargot ravioli with chunky bacon.

In New York City, kick off your culinary tour with grilled pork loin with braised fennel and blood orange at Mario Batali's Babbo, where you'll also find the afore-mentioned grilled quail, and then head uptown for frisky soul food, like catfish with grits and fried green tomatoes at Marcus Samuelsson's funky Red Rooster in Harlem.

In the end, though, the greatest culinary rivalry between both cities is something very simple: pizza. Which is better: deep-dish Chicago style or thin-crust New York? Either way, you'll eat well—and the debate will probably go on forever. Just don't try to eat that New York slice with a fork.

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