CHICAGO is in many ways the nation’s last great city. Sarah Bernhardt called it “the pulse of America” and, though long eclipsed by Los Angeles as the nation’s second most populous city after New York, Chicago really does have it all, with less hassle and fewer infrastructural problems than its coastal rivals.

Most visitors to Chicago are immediately bowled over by its magnificent urban skyline, adorned with one of the world’s finest assemblages of modern architecture, ranging from Mies van der Rohe’s masterpieces on the campus of the Illinois Institute of Technology to the 110-storey Willis Tower (more commonly known by its former name, Sears Tower). The city is also rightly quite proud of the wonderful Millennium Park and the extraordinary treasures of the Art Institute of Chicago, as well as several other excellent museums. The city’s strongest suit is live music, with a phenomenal array of jazz and blues clubs packed into the back rooms of its amiable bars and cafés. The rock scene is also healthy, having spawned such bands as Smashing Pumpkins and Wilco during the 1990s and R&B stars R. Kelly, Kanye West and Lupe Fiasco in recent years. And almost everything is noticeably less expensive than in other US cities – eating out, for example, costs much less than in New York or LA, but is every bit as good.

Brief history

Founded in the early 1800s, Chicago had a population of just fifty in 1830. Its expansion was triggered first by the opening of the Erie Canal in 1825, and then by the arrival of the first locomotive in 1848; by 1860 it was the largest railroad centre in the world, serving as the main connection between the established East Coast cities and the frontier that stretched more than two thousand miles west to the Pacific Ocean. That position on the sharp edge between civilization and wilderness made it a crucible of innovation. Many aspects of modern life, from skyscrapers to suburbia, had their start, and perhaps their finest expression, here on the shores of Lake Michigan.

The furious pace of development was briefly halted in 1871 when the Great Chicago Fire destroyed much of the urban fabric. Chicago boomed thereafter, doubling in population every decade. The nickname “Windy City” was coined by a New York newspaper editor in the 1890s to describe the boastful claims of the city’s promoters when attempting to lure investors from the eastern United States. By 1900 the city was home to more than two million people, many of whom made their way on crowded ships from Ireland and Eastern Europe. In the early years of the twentieth century, it cemented its reputation as a place of apparently limitless opportunity, with jobs aplenty for those not averse to strenuous physical labour and largely monotonous tasks in factories, stockyards and railroad facilities. The attraction was strongest among blacks from the Deep South: African Americans poured into the city, with more than 75,000 arriving during the war years of 1916–18 alone.

During the Roaring Twenties, Chicago’s self-image as a no-holds-barred free market was pushed to the limit by a new breed of entrepreneur. Criminal syndicates, ruthlessly run by the likes of gangsters such as Al Capone and Bugs Moran, took advantage of Prohibition to sell bootleg alcohol. Shootouts in the street between sharp-suited, Tommy-gun-wielding mobsters were not as common as legend would have it, but the backroom dealing and iron-handed control they pioneered was later perfected by politicians such as former mayor Richard J. Daley who ran Chicago single-handedly from the 1950s until his death in 1976. Today’s mayor, former President Obama staffer Rahm Emanuel, with his slightly abrasive and heavy-handed approach, seems to be continuing the tradition.

Accommodation in Chicago

Most central accommodation is oriented toward business and convention trade rather than tourism, but there are still plenty of moderately priced rooms in and around the Loop, to say nothing of the myriad of establishments that are scattered alongside major interstates. Even top-class downtown hotels are, comparatively, not that expensive. Note, however, that a room tax of 16.4 percent is added to all bills, while overnight parking can cost $2 at a modest downtown hotel, and as much as $47 at a fancy one. If you’re stuck, try Hot Rooms, a reservation service offering hotel rooms at discount rates. While they’re not as prominent as elsewhere, B&B rooms are available from around $90/night; the Chicago B&B Association maintains full listings.

Chicago guided tours

The best guided tours of Chicago are those offered by the Chicago Architecture Foundation, based in the Archicenter in the Santa Fe Building at 224 S Michigan Ave. Expert guides point out the city’s many architectural treasures and explain their role in Chicago’s history and development. Most popular of all are the superb Architecture River Cruises along the Chicago River that leave from Michigan Avenue and Lower Wacker Drive. The Foundation also runs several walking tours of the Loop, departing from the Archicenter on a complicated schedule of at least two different two-hour tours daily throughout the year ($17 each), and a daily 45-minute, $5 lunchtime tour of downtown landmarks at 12.15pm.

For a free and personalized tour, the Chicago Greeter programme is an excellent choice. Tours leave from the lobby of the Chicago Cultural Center and you can set up a tour beforehand by contacting the website several weeks in advance. Alternately, just show up and take advantage of the “Instagreeter” programme. The tours are led by a trained greeter and cover about 25 different neighbourhoods, or you can pick one of the forty themed tours such as “Gay & Lesbian Chicago” or “Green Chicago”.

Chicago spectator sports

Chicagoans are, for better or worse, loyally supportive of their teams. The city’s most successful outfit in recent memory was the Bulls basketball team, helmed by Michael Jordan and winner of six NBA championships in the 1990s. Now, though, with the Jordan era long gone, Bulls fans have little to cheer about, though the team’s fortunes have improved in recent years. They play in the modern and severe United Center, 1901 W Madison St, as do hockey’s Blackhawks, who triumphed in 2010 and 2013 to become the Stanley Cup champions. The Bears football team can be seen at the 61,500-capacity Soldier Field, 425 E McFetridge Drive, at the south end of Grant Park. As for baseball, neither Chicago team had won a World Series since 1917 until the White Sox finally broke the streak in 2005. They play their contests at the distinctly nondescript US Cellular Field stadium, at 333 W 35th St on the South Side. The long-suffering Cubs still call grand old Wrigley Field home.

Drinking in Chicago

Chicago is a consummate boozer’s town, and one of the best US cities for bars, catering to just about every group and interest, with many open until 3, 4 or even 5am. The city’s drinking areas include the touristy Division Street, the post-college melange that is Wrigleyville and a clutch of places in bookish Hyde Park. Wicker Park is the trendiest hangout zone, while Halsted Street between Belmont and Addison is known as Boystown for its gay bars and clubs. The hundred-plus cafés and coffeehouses across the city may not have taken the place of the traditional taverns, but they’re a growing alternative.

Eating in Chicago

Chicago’s cosmopolitan make-up is reflected in its plethora of ethnic restaurants. Italian food, ranging from hearty deep-dish pizza – developed in 1943 at Pizzeria Uno – to delicately crafted creations presented at stylish trattorias, continues to dominate a very dynamic scene. In recent years there’s been a surge of popularity for New American cuisine. Thai restaurants still thrive, as do ones with a broad Mediterranean slant, many of which serve tapas; and there are still plenty of opportunities to sample more long-standing Chicago cuisines – Eastern European, German, Mexican, Chinese, Indian, even Burmese and Ethiopian. Of course, a number of establishments serve good old-fashioned BBQ ribs, a legacy of Chicago’s days as the nation’s meatpacker. And no visit is complete without sampling a messy Italian beef sandwich, or a Chicago-style hot dog, laden with tomatoes, onions, celery salt, hot peppers and a pickle. The largest concentration of restaurants is found north and west of the Loop. To the west, Greektown, around Halsted Street at Jackson Boulevard, and Little Italy, on and around Taylor Street, are worth a look, while the Near North and River North areas harbour a good number of upmarket places.

Lincoln Park

In summer, Chicago’s largest green space, Lincoln Park, provides a much-needed respite from the gridded pavements of the rest of the city. Unlike Grant Park to the south, it’s packed with leafy nooks and crannies, monuments and sculptures, and has a couple of friendly, family-oriented beaches at the eastern ends of North and Fullerton avenues. Near the small zoo at the heart of the park (late May to Oct Mon–Fri 9am–6pm, Sat & Sun 9am–7pm; Nov–May daily 9am–4.30pm; free), renowned for its menagerie of African apes and curious red pandas, you can rent paddleboats or bikes. If the weather’s bad, head for the pleasantly humid conservatory, 2400 N Stockton Drive (daily 9am–5pm; free), or bone up on Chicago’s captivating past at the Chicago History Museum, at the south end of the park at 1601 N Clark St (Mon–Sat 9.30am–4.30pm, Sun noon–5pm; $14; T312 642 4600, Wchicagohistory.org), with comprehensive displays on regional and national history, including some rather twee dioramas depicting the Great Fire of 1871 and the World’s Columbian Exposition.

The Lincoln Park neighbourhood, inland from the lake, centres on Lincoln Avenue and Clark Street, which run diagonally from near the Historical Society Museum; Halsted Street, with its blues bars, nightclubs and myriad restaurants, runs north–south through the district’s heart. Any of these main roads merits an extended stroll, with forays into the many book- and record stores. Look for the Biograph Theatre movie house (now a live theatre stage), 2433 N Lincoln Ave, where John Dillinger was ambushed and killed by the FBI in 1934, thanks to a tip from his companion, the legendary Lady in Red.

Millennium Park

Until the late 1990s, the area that is downtown’s Millennium Park was a rather dreary-looking, albeit well-located, slice of real estate. Thanks to a highly ambitious (and hugely expensive, to the tune of $475 million) renovation project that long overran its original 2000 completion date, it’s a showcase for public art, landscape design and performing arts. Its twin artistic centrepieces are equally compelling. First is a stunning, seamless, stainless-steel sculpture officially titled Cloud Gate but universally known as “the Bean”, by British-based artist Anish Kapoor. Inspired by liquid mercury, it invites viewers to walk around, beside and even underneath it to enjoy spectacular and endlessly intriguing reflections of both the city and the sky above it. Nearby, Crown Fountain by Jaume Plensa consists of two glass-brick towers set either side of a black granite plaza; giant video images of the faces of ordinary Chicagoans play across them both, and water spurts from them in summer at unexpected intervals to form a lake that’s usually filled with playing children. Further back, the Jay Pritzker Pavilion is an amazing open-air auditorium designed by Frank Gehry, who used mighty swirls and flourishes of steel to improve its acoustics. Finally the Lurie Garden features more than 26000 plants in total, representing more than 250 varieties native to the Illinois prairie.

Chicago nightlife and entertainment

From its earliest frontier days, Chicago has had some of the best nightlife in the USA. Blues fans who celebrate Chicago as the birthplace of Muddy Waters’ urban blues will not be disappointed. The city remains proud of its blues traditions, while continuing to innovate in other genres, such as the energetic dance beat of 1980s house music as well as the groundbreaking jazz of the Art Ensemble of Chicago. There are nightclubs aplenty all over town, especially along Halsted Street, Lincoln Avenue and Clark Street on the North Side. Uptown, at the intersection of North Broadway and Lawrence, has a couple of excellent venues for jazz and rock. The best gay clubs congregate in the Boystown area, which is a mile north of Lincoln Park. Highbrow pursuits are also well provided for: Chicago’s classical music, dance and theatre are world-class. For listings, Chicagoans pick up free weeklies including the excellent Chicago Reader (available Thurs afternoon and online at Wchicagoreader.com), the New City and the gay and lesbian Windy City Times. The Friday issues of the Chicago Sun-Times and the Chicago Tribune are useful, while Time Out Chicago has good arts, music, theatre and movie listings.

The Art Institute of Chicago

The Art Institute of Chicago ranks as one of the greatest art museums in the world, thanks to a magnificent collection that includes, and extends way beyond, Impressionist and Post-Impressionist paintings, Asian art, photography and architectural drawings. While the Neoclassical facade of the main entrance does its best to look dignified, the numerous added-on wings can make it hard to find your way around. In 2009, the museum also opened its new Modern Wing, designed by “starchitect” Renzo Piano.

Most visitors head straight upstairs to the Impressionist works, which include a wall full of Monet’s Haystacks captured in various lights, next to Seurat’s immediately familiar Pointillist Sunday Afternoon on La Grande Jatte. A handful of Post-Impressionist masterpieces by Van Gogh, Gauguin and Matisse are arrayed nearby. Beyond these masterworks, other highlights include the pitchfork-holding farmer of Grant Wood’s oft-parodied American Gothic, which he painted as a student at the Art Institute school, and sold to the museum for $300 in 1930; El Greco’s 1577 Assumption of the Virgin; Edward Hopper’s lonely Nighthawks; Pablo Picasso’s melancholy Old Guitarist, one of the definitive masterpieces of his Blue Period; a tortured, tuxedoed self-portrait that was Max Beckmann’s last Berlin painting before fleeing the Nazis; canvases by Jackson Pollock and Mark Rothko; and several works by Georgia O’Keeffe, such as a 1926 depiction of New York’s Shelton Hotel, where she was living.

The Chicago River

The Loop is usually said to end at the “L” tracks, but the blocks beyond this core, to either side of the Chicago River, hold plenty of interest. Broad, double-decked Wacker Drive, parallel to the water, was designed as a sophisticated promenade, lined by benches and obelisk-shaped lanterns, by Daniel Burnham in 1909. Though never completed, and despite the almost constant intrusion of construction works, it makes for a nice extended walk. The direction of the river itself was reversed a century ago, in an engineering project more extensive than the digging of the Panama Canal. As a result, rather than letting its sewage and industrial waste flow east into Lake Michigan, Chicago now sends it all south into the Corn Belt.

A boat tour from beneath the Michigan Avenue Bridge gives magnificent views of downtown. However, half an hour’s walk, especially at lunchtime when the office workers are out in force, will do the trick nearly as well. Burnham’s promenade runs along both sides of the river, crossing back and forth over the twenty-odd drawbridges that open and close to let barges and the occasional sailboat pass. The State Street Bridge makes a superb vantage point. On the south bank, at 35 E Wacker Drive, the elegant Beaux Arts Jewelers Building was built in 1926 and is capped on the seventeenth floor by a domed rotunda that once housed Al Capone’s favourite speakeasy.

Willis Tower

The 1451ft Willis Tower (formerly the Sears Tower), was the tallest building in the world until 1998, when Malaysia’s Petronas Towers nudged it from the top by the length of an antenna; both have since been eclipsed by further construction projects in Taiwan and the Middle East. Various companies occupy the tower (Sears moved out in the early 1990s), and it’s so huge that it has more than one hundred elevators. Two ascend, in little more than a minute, from the ground-level shopping mall to the 103rd-floor Skydeck Observatory for breathtaking views that on a clear day take in four states – Illinois, Michigan, Wisconsin and Indiana. Visitors can also peer down onto the city from one of the elaborate glass boxes that hang off the side of the Skydeck. Look east for the distinctive triangular Metropolitan Detention Center, where prisoners exercise on the grassy roof beneath wire netting to ensure they don’t get whisked away by helicopter.

Wrigley Field

In the 1800s thousands of German immigrants settled in what was then the separate enclave of Lakeview, which was annexed to the city formally in 1889. This area is now called Wrigleyville in honour of Wrigley Field, 1060 W Addison St at N Clark St, the ivy-covered 1920s stadium of baseball’s much-loved Cubs, and one of the best places to get a real feel for the game. There are few more pleasant and relaxing ways to spend an afternoon than drinking beer, eating hot dogs and watching a ballgame in the sunshine, among the Cubs’ faithful. Two-hour field tours run from May through September on select days (every 30min 10am–4pm), and cost $25.

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