Great Golf Top 100
The Luxury Travel and Lifestyle Magazine

Chicago - Golf, Jazz and Blues


Standing tall on the shores of Lake Michigan, Chicago is a beguiling city that is fun to explore on a short break, from its wealth of attractions to a music scene that encompasses much more than its famous jazz and blues. It also has fabulous golf on its doorstep. Peter Ellegard reports.


With its soaring citadels of steel, concrete and glass, Chicago has one of America’s most recognisable skylines. Its skyscraper forest incorporates the second tallest building in the western hemisphere – the Willis Tower.     Originally the Sears Tower, the Willis Skydeck observatory offers visitors a heart-stopping thrill with The Ledge. Glass boxes jut out from the 103rd-floor, so visitors can look straight down to the streets 1,353 feet below and over the city as though suspended in mid-air.
    Rival sky-high observatory 360 Chicago (the former John Hancock Observatory) sits on the 94th floor of the John Hancock Centre – 1,000 feet above Chicago’s Magnificent Mile shopping thoroughfare, North Michigan Avenue. Its new Tilt attraction comprises a steel-framed glass platform that slowly tilts out to 30 degrees, giving breathtaking downward-facing views of terra firma. Terror firmer might be more appropriate…
    Chicago’s high-rise edifices have helped earn it the Windy City soubriquet since the late 1800s, because of the funnelling effect at street level. Its famous ‘L’ trains ride high on elevated tracks as they circle the downtown Loop district and radiate beyond.



It’s in unassuming, often ramshackle buildings elbowed aside by mighty monoliths where you find Chicago’s heart; in clubs and bars where jazz, blues and other music genres (house music was born in Chicago) set the beat.
    The term ‘jazz’ was coined in Chicago around 1915, although the blues predates it. Blues homeland is south of the Chicago River that flows through the city, aka the South Side – resonating through clubs such as Buddy Guy’s Legends. Many leading exponents have played there and memorabilia on its walls pay homage to musical greats, not least to blues legend Buddy Guy himself. In his late 70s, he still plays there when not touring, and I was lucky enough to meet him there on a previous visit.
    Uptown, north of the river, is where jazz put down its roots during the Prohibition. A favourite haunt of Al Capone, the Green Mill Cocktail Lounge still survives – its art nouveau decor, moody lighting and soulful singers, such as ‘Flapper Girl’ Erin McDougald, evocatively recreating the 1920s and 1930s ambience. It still has underground tunnels, accessed via a trapdoor from the days when Capone and other patrons needed a quick escape to surrounding streets during police raids.
    Red Line ‘L’ trains clatter over nearby elevated tracks 24/7, offering easy access from downtown Chicago, and past the fading Moorish façade of the old jazz dance hall, the Aragon Ballroom, which now stages lively music concerts.
    For alternative nightlife, take in one of the city’s many shows, from Broadway productions to the clever and funny improvised humour of The Second City, again very accessible via Chicago’s excellent public transport system.
    Chicago also has a lively festival scene; the Chicago Blues Festival each June and Chicago Jazz Festival every August are both free and hugely popular.

CHICAGOLAND GOLF. Golfers visiting Chicago can easily mix a city stay with a round or two in the Chicagoland suburbs. Medinah, where Europe memorably retained the Ryder Cup in 2012, is members-only but visitors are welcome at The Glen Club, in nearby North Shore community Glenview. Here, a highly-rated Tom Fazio course sits on a 195-acre site that was formerly the Glenview Naval Air Station. The runways, hangars and flat terrain have been replaced with a natural-looking course featuring dramatic elevation changes, lakes, streams, mature trees and swathes of prairie grass.
    The course was sadly still closed when I visited in early April, following one of Chicago’s longest and harshest winters ever. Notable holes include three demanding par-3s: the short but deceptive 4th and the 11th and 17th, where water guards the entire left side of both. The picturesque, risk-reward par-5 18th hole ends in front of the grand clubhouse, which also offers stylish accommodation upstairs and fine dining in the Glen Club Grill.
    The Glen Club is a brief train ride from Chicago. Amtrak and high-speed Metra trains run from the city centre to Glenview, leaving a short walk to the club.


COG HILL. You will need a car to play at family-owned Cog Hill Golf & Country Club, 30 miles south-west of Chicago. But it would be a crime to visit Chicago and not venture there to play at least one of its four courses. I rented an Alamo car through Your Car Hire (, which specialises in renting to golfers and is bookable via travel agents at Chicago’s O’Hare Airport. I returned it two days later to get a train downtown.
    Cog Hill’s most illustrious layout is Course No. 4. Nicknamed ‘Dubsdread’ because of the fear in instils in poor golfers, it was created by Dick Wilson and Joe Lee and opened in 1964, being revamped 45 years later by Rees Jones.
    Host to PGA Tour events, including the BMW Championship and the US Amateur Championship, its gargantuan sculpted bunkers and wicked sloping greens made me grateful that I was only viewing it on a buggy tour in the bitingly-cold winds. Of its four par-3 holes, the long and difficult 6th stands out. Cog Hill really comes into its own on the hilly loop from the 12th to the 16th; the views are stunning but slice at your peril, and mind those gaping bunkers.
    I was able to play the No. 2 course, Ravines. A friendlier challenge for high handicappers like me, it still tests your game, particularly on holes crossed by the deep ravines from which it is named.


STAY IN STYLE. The grand, century-old landmark Renaissance Blackstone Hotel on South Michigan Avenue is a great base from which to explore the city and lakefront rooms offer stunning views. Previously owned by the Beatles’ guru, the Maharishi Yogi, it has been restored to its former glory in a $126 million renovation.
    The hotel is just a block from Buddy Guy’s Legends. I also walked from it to the Willis Tower, took in Millennium Park to photograph reflections in its popular, mirrored bean-shaped sculpture, shopped at iconic store Macy’s and boarded Chicago’s First Lady boat for a fascinating narrated Chicago River cruise through the city. Operated in conjunction with the Chicago Architecture Foundation, this tour is a must.

OTHER ATTRACTIONS. Chicago has so much to see and do, you will only scratch the surface on a city break. But if time allows, visit the Museum of Science and Industry and walk through a German U2 submarine, ride the Ferris wheel on Navy Pier, catch a Cubs baseball game at Wrigley Field (100 years old this year). Why not take a blues and jazz tour with Chicago Detours, explore one of Chicago’s 77 eclectic neighbourhoods or simply chill out at a free open-air concert at Frank Gehry’s Jay Pritzker Pavilion in Millennium Park.
    Besides being the home of the deep-dish pizza, Chicago is also a foodie’s heaven and home to the nation’s top-rated restaurant, Alinea, among many other gourmet establishments. One of the latest fashions is the ‘bacon bar’, where you can sip drinks while snacking on crispy strips of bacon.
    As the famous song goes: “Chicago, Chicago, it’s a toddlin’ town”. Take note and amble around this impressive city to soak up the atmosphere. It definitely won’t give you the blues.


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Photos courtesy of Peter Ellegard and resorts