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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 ...

It's been a long day of business in Chicago and you're looking to end your day on a different note: a pleasant stroll, some shopping, a good meal, a few drinks and a bit of entertainment before you fly home. Here’s an easy walking tour that should fit the bill.

On my last trip to the Windy City, I started by exploring the city's “front yard,” magnificent Grant Park, which stretches several kilometres along the shore of Lake Michigan right off The Loop. This peaceful oasis in the heart of the city not only offers walking and bike trails to get some stress-relieving exercise but it's also home to several noteworthy attractions.

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If your day ended a bit early and you only have time for one stop, make it the Art Institute of Chicago. Near the middle of the park on its western edge, the AIC boasts a fantastic collection of Impressionist art, and its collection of works by American painters, sculptors and photographers has few peers. On of its many treasures to seek out is America Windows, stained glass created by French Impressionist Marc Chagall. It was donated to the museum during the U.S. 1976 Bicentennial in memory of political powerhouse Mayor Richard J. Daley. AIC’s holdings also include ancient coins and textiles dating back as far as 300 BC. If you’re in town on a Thursday, you’ll have more time to explore as the AIC stays open to 8 p.m.

I also enjoyed the Shedd Aquarium at the southern end of the park, which offers you the chance to explore marine habitats and more in its Waters of the World exhibit. The Adler Planetarium, built in 1930 and the first of its kind in the United States, is also nearby. Most workdays you’d have to nip in during lunch, but every third Thursday of the month, the planetarium offers Adler After Dark from 6 p.m. to 10 p.m.

If you want to shop for a few gifts to take home to family, leave Grant Park and walk north into what’s called the Gold Coast district along North Michigan Avenue to the Magnificent Mile , as the stretch between the Chicago River and Oak Street is known – and get ready to melt your plastic.

Three high-rise malls – Watertown Place, 900 North Michigan Shops and The Shops at North Bridge – are home to the world's biggest names in retailing.

But don't forget to look around as you browse the many other store windows along the way. The Mile is home to some incredible architecture, including the old Water Tower, which survived the great fire of 1871, the Gothic spires of the Chicago Tribune Buildingand the 110-storey Willis Tower (formerly the Sears Tower), once the world's tallest building and still the tallest in the U.S. And be sure to stop in at Macy's if only to see the magnificent Tiffany-designed glass mosaic ceiling in the former Marshall Field’s department store.

By now you may be feeling a bit peckish. The Gold Coast offers a wide range of great dining experiences, but first, take a minute to experience the big picture.

Adjacent to the Water Tower is the John Hancock Observatory, billed as “Chicago’s Greatest High.” Take the fastest elevator in the U.S. (1,000 feet in 40 seconds) up to the 94{+t}{+h} floor and take in the amazing view – either from inside the observatory or on its open-air sky walk – that stretches beyond Illinois to three neighbouring states: Indiana, Wisconsin and Michigan.

By night, the view of Chicago's distinctive skyline is striking. One more floor up, the upscale Signature Room at the 95th (or its lounge at the 96th!) is the perfect place to linger over dinner and drinks (or return later for a nightcap).

Back at ground level, Rush Street is home to some of the best restaurants in the city. Gibson’s Bar and Steakhouse boasts an exceptional wine list, great food (critics rave) and large portions (pace yourself). Other noteworthy entries at the top of the food chain include the Italian steakhouse Phil Stefani's 437 Rush and Bistrot Zinc for a taste of fine French cuisine.

My favourite Chicago culinary experience is a little more down-scale. No visit to the Windy City would be complete without sampling its hometown specialties, in particular its legendary deep-dish pizza. I enjoyed my pie at Pizano’s Pizza and Pasta,and while the menu includes traditional Italian entrees and even a half-pound burger, the pizza is the story and the prices are reasonable. Some locations have special offers that can make it even more economical. (www.pizanoschicago.com)

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

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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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