Chicago vs Manhattan

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

ABOVE Art Deco façade of the Chicago Board of Trade building BELOW The impressive Chicago skline viewed from a riverboat cruise
ABOVE Art Deco façade of the Chicago Board of Trade building BELOW The impressive Chicago skline viewed from a riverboat cruise


LOCATION On the shores of Lake Michigan, in the state of Illinois, 714 miles (1,150 km) west of New York City


45 million WEATHER Chicago has hot, sunny but humid summers and bitterly cold, snowy winters.

Spring and fall are lovely, though nights may be chilly

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.

The Great Chicago Fire of 1871 completely devastated the heart of this wealthy industrial city, but it also created a blank slate. As Chicago was rebuilt, talented architects rushed in from Europe and the east coast, eager to try out new forms and ideas unfettered by traditional styles and constraints. Among them were Louis H. Sullivan, John Root, Daniel Burnham, and William le Baron Jenney. The “father of the skyscraper,” Jenney invented the metal-frame construction method that made such high-rise buildings possible.

While New York so often tore down its old buildings to make room for the new, in Chicago you can still see some of the earliest skyscrapers ever built. The Rookery, Marquette, Monadnock, and Reliance buildings were all erected between 1885 and 1895. They sport such features as decorative terracotta façades and Jenney’s trademark Chicago windows with narrow opening side panels. Their distinctive style has become known as the Chicago School of Architecture.

You’ll trek miles to take in New York’s landmark buildings, but many of Chicago’s architectural gems lie within The Loop, the historic city center beneath the “El.” The clattering of this elevated train system adds to the urban buzz as workers and visitors bustle between shiny new office blocks, grand old hotels and department stores, cozy corner bars, and art-decked public plazas.

The Chicago Architecture Foundation leads a wide range of tours of this vibrant downtown area as well as a skycraper-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, spiralling residential tower will stand 2,000 ft (610 m) high. Take a water taxi up the Chicago River for more fine 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.


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.


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.

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