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Summer day in Chicago (Henryk Sadura/Getty Images/iStockphoto)
Summer day in Chicago (Henryk Sadura/Getty Images/iStockphoto)

Winding down in the Windy City Add to ...

The Gold Coast also offers a wealth of entertainment options, starting with The Second City comedy club. The troupe that launched the careers of comedians such as Dan Aykroyd, Andrea Martin, Bill Murray, and John Belushi is still going strong and well worth a visit (the current show is called South Side of Heaven). If you want something a little different and you’re free at 4 p.m. on a Wednesday or 1 p.m. on Sunday until Oct. 30, you can take The Second City’s Neighbourhood Tour, which takes in the company’s Old Town neighbourhood and its architecture, pointing out favourite spots of some Second City alums.

I’m a sucker for jazz bars, and the Gold Coast has a couple of nice ones, including Jilly’s , an intimate spot revered by Sinatra fans, with a pub-food dinner menu.

Chicago's blues scene is world famous, with a host of clubs large and small. In the Gold Coast, a small club called Proof features a potent mix of cocktails and live music. However, purists will want to hop in a cab and head west to Rosa's Lounge (for a blues jam on a Thursday night or featured artists on the weekend),or south to Buddy Guy's Legends. If you travel with your axe (it would have to be a harmonica), check out the Ten Spot Workshops once-a-month on Mondays, where $10 buys you a blues workshop (Jazz for Blues Players on Oct. 24) and admission to the regular jam.

One final entertainment suggestion: Tickets are hard to come by, but no self-respecting Canadian would visit Chicago without at least trying to catch a Blackhawk’s game at the United Center. Try Stub Hub (www.stubhub.com) for possible late seating.

To round things off, (if you’re not too tired) head back to the Signature Lounge atop the Hancock Center, and relax while taking in the spectacular view at night, sparkling with light.

You can get enough of a feel for Chicago during a business trip that you’ll know what you want to experience the next time business takes you there –and for sure you’ll want to return for fun.

Special to The Globe and Mail


An evening in the Windy City

1. Take a walk in Grant Park at 5:30

As soon as you’ve finished your last handshake, head toward Chicago’s Grant Park for a walk, to stretch your legs and clear your head. The park features kilometres of bicycle paths amid forest groves and along Lake Michigan, and its level topography make it an easy ride, so a great way to see as much as you can in limited time is by renting a bicycle from outfits such as Bobby's Bike Hikes (http://www.bobbysbikehike.com/Tours.aspx) or Bike Chicago (http://www.bikechicago.com/). If your meetings ended early, make directly for the Art Institute of Chicago, and take in a soothing hour of visual art to change gears.

2. Relax with a drink atop Hancock Observatory at 6:30

Take the fastest elevator in the United States to the 94th floor of the Hancock Building ... then walk up two more floors to the Signature Lounge at the 96th. Have a drink as you enjoy the unparalleled view that includes four states, Wrigley Field (home of the Cubs), and the Navy Pier (the grand old amusement park with its signature Ferris wheel), that extends out into Lake Michigan.

3. Windowshop and sightsee along The Magnificent Mile at 7:30

This stretch of Michigan Avenue is a shopper's paradise, boasting the biggest names in world retailing all within a few blocks. It is also home to some of the city's most striking architecture, including the old Water Tower, which survived the Great Fire of 1871, and the Willis (formerly Sears) Tower.

4. Enjoy some Dinner at 8:15

Choices are plentiful on Rush Street, from Gibson’s Bar and Steakhouse, to Italian at Phil Stefani’s or French cuisine at Bistrot Zinc. If fine cuisine feels like too much, there’s always deep-dish pizza at Pizano’s.

5. Listen to some Blues (and maybe have a nightcap) at 10:30

You can’t go to Chicago without experiencing the blues scene. Numerous clubs offering everything from top-name entertainment to local bands looking to make a name for themselves. At the top of the list are Rosa's (www.rosaslounge.com) and Buddy Guy's Legends (www.buddyguy.com), but don't be afraid to investigate smaller venues, such as Proof, a Gold Coast club with a growing reputation (www.proofchicago.com), or Jilly's, a piano bar with great ambience (www.jillyschicago.com)before returning to your hotel to hit the hay.

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