Compare Cities Chicago vs Manhattan

Manhattan’s soaring skyline dazzles, but Chicago is the birthplace of the skyscraper

New York’s skyscrapers may be the most famous in the world but, in the architectural race to the top, Chicago has always had the Big Apple beat, literally, from the ground up. The first skyscrapers were erected, not in the great eastern metropolis, but here on the edge of the Midwestern prairie, and present-day Chicago offers a fascinating visual history of the rise of the modern urban landscape.

Forget New York?

The build-up

The Empire State Building is an American legend. The Chrysler Building spire, Rockefeller Center, and the Flatiron Building are among many other skyscrapers known the world over from movies and TV.

The letdown

New York’s architectural icons are scattered over several miles, from the tip of Lower Manhattan to the top of Central Park. The best features of many are at the top, only clearly visible from the upper floors of other skyscrapers. Few of these are open to the public, so expect long lines, security searches, and costly admission to observation decks.

Going anyway?

Pack comfortable shoes, binoculars, and extra patience. Pre-purchase Empire State Building tickets online and, if time is tight, consider an Express Pass.

Practical information

Getting There and Around

O’Hare International Airport, 17 miles (27 km) northwest, and Chicago Midway Airport, 8 miles (13 km) southwest, are connected to The Loop by train. This is the cheapest and fastest way to downtown, especially during rush hour.

Where to Eat

Chicago has a sophisticated dining scene as well as a great range of casual and ethnic restaurants. Deep-dish pizza is a Chicago specialty. Try it at Pizano’s, a restaurant and sidewalk café in The Loop, still run by the family who invented the dish.

Where to Stay

The luxurious Hotel Burnham ( is a boutique hotel named after the architect and set in his landmark Reliance Building in The Loop.

When to Go

Summer has the warmest weather. Spring and fall are also good for outdoor architecture-viewing but bring a warm, windproof jacket.

Budget per Day for Two

US$220–375, depending on your choice of accommodations and dining options.

Last word

The Chicago Architecture Foundation leads a wide range of tours of this vibrant downtown area as well as a skyscraper-spotting riverboat cruise. Highlights include Sullivan’s ornate Carson, Pirie, Scott & Company building (1899); the striking Art Deco skyscraper of the Chicago Board of Trade (1930); and the minimalist “glass box” Federal Center by Ludwig Mies van der Rohe (1959–74).

The 1,450-ft (442-m) Willis – formerly Sears – Tower (1973) is currently the nation’s tallest building, beating the Empire State Building by 200 ft (61 m). From its Skydeck observatory on the 103rd floor, you can see four states. Under construction on the lakefront nearby is Santiago Calatrava’s, Chicago Spire. When completed, this elegant, spiraling residential tower will stand 2,000 ft (610 m) high. Take a water taxi up the Chicago River for finer skyline views on your way to Navy Pier, on Lake Michigan. In summer, this entertainment and dining center offers everything from a fairground to a Museum of Stained Glass, as well as year-round live events.

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