Chicago, Illinois

A top destination for shopping, dining, and more!

Where can you go for amazing shopping, fabulous dining, worldly wines, great sightseeing, and a vibrant arts and entertainment scene?  Chicago has it on all counts.  (And I don’t have to suffer the frustrations of flying there!  An easy day’s drive gets me there with excitement every time.) 

There's so much to see and do in Chicago that my husband and I are never at a loss.  Do some research before you go and plan your time well.  Go once and you’ll go back often.  

Chicago Shopping

Chicago is the second top shopping destination in the U.S. (Manhattan claims the #1 spot).  You won’t be disappointed.  There are so many shops, boutiques, and department stores to choose from.  Fairly close to each other downtown there are five top name department stores - Saks Fifth Avenue, two Macy's, Neiman Marcus, Bloomingdale’s, and Nordstrom.  Of note is Macy’s on State Street, in an historic building dating to 1906 which contains the famous Tiffany vaulted ceiling - the first and largest ceiling ever built has 1.6 million pieces of glass!  It’s worth a store visit just to see that beautiful ceiling, though you’ll find the entire store architecturally stunning.  

Familiar to many is the Magnificent Mile, an amazing array of designer stores all within walking distance along Michigan Avenue.  Ferragamo, Chanel, St. John, Allen-Edmonds, Burberry, Louis Vuitton, Hugo Boss, Giorgio Armani, Escada, Prada, and more.  The stores' architecture is beautiful both on the outside and inside.  Service is top-notch everywhere.  Sales staff is very knowledgeable with genuine interest in serving customers.  How refreshing! 

Even on my visit early in March (not the best time - though as is always my luck in life, it was perfect weather for the drive and Chicago had no snow in sight)… summer clothes were plentiful both for styles and sizes.  Spring clothes were already on sale at great discounts, and fall fashion was talked about as shoppers put in orders for items due to arrive in August.  

To say shopping in Chicago is exciting is an understatement.  Luxury labels are everywhere with selections that astound whether it’s fine linens, quality leather goods, the latest in housewares, antiques, fine art or jewelry.  Calls to a few chosen stores before I left was a smart move.  Those merchants set aside items we were interested in seeing, and one store anticipated our taste and selected additional items for us to look at when we arrived.  I’ve always been most impressed with service in the U.S. - whether at a bargain basement or a luxury label.  

I don't always have enough time to get to other parts of the city, but don’t miss the mostly smaller boutiques in Bucktown, Wicker Park, and Lincoln Park who boast some of the finest shopping in the world. 

Chicago Dining

What do you do after full days of shopping?  Wine and dine, of course.  Chicago has an amazing list of excellent eateries whether it’s for their famous deep-dish Chicago style pizza (don’t miss it!), or a meal at one of their top restaurants.  We weren’t disappointed with a single meal - of course, I did my research beforehand and made reservations well in advance in some cases. 

Tasting menus are in vogue with less attention paid to the a la carte items it seems.  Our meal at Everest was special, not only for its fine tasting menu but for the view of the city and the décor.  Les Nomades was my husband’s top pick offering mostly tasting menus.  The room is sophisticated and warm, and the service impeccable without an air of superiority on the part of any of the staff.  As a rule, I don’t prefer tasting menus (numerous small portions that can be paired with wines), but both these restaurants offer wonderful tasting selections with unusual wine pairings of quality.  

Don’t miss out on some of the foods that have made Chicago famous.  Their deep dish pizza is unique and raved about around the world by pizza lovers who like a thick “crusty" crust with fresh toppings layered differently than the usual served in North America.  We ordered a medium sized pizza to have extra for our drive home the next day (yes, their pizza tastes great cold!) but our server, thinking we didn’t know how large their sizes are, placed an order for a small.  Even a small was larger than we could both eat!  Chicago's famous hotdogs shouldn’t be missed either.  And be sure to head to any one of Garrett’s Popcorn locations.  There are two within close proximity on the Magnificent Mile.  This is Halle Barry’s favourite snack food.  Garrett’s popcorn is always made fresh with the freshest premium ingredients.  Try the macadamia nut loaded with nuts and super coated or their famous cheese popcorn made with real cheese!  It’s definitely worth the wait in line - though we go at off hours so that we can spend more time sightseeing.  


Chicago’s architecture can’t be beat which is why pedestrians - tourists and locals alike - spend so much time gawking up at the sky fascinated by all those wonderful buildings.  Whether it’s Frank Lloyd Wright or dozens of other world famous architects, you’ll find it all here.  There are tours, museums, book stores, and more all dedicated to it.  My husband and I could spend hours fascinated by the way sun strikes a building or rain darkens its stone.  And in winter, you’ll see their famous sidewalk signs, “Caution falling ice".  

Perhaps next time, I’ll write about their arts and entertainment scene.  We both love jazz music and Chicago’s jazz venues and festivals rival those of New Orleans, Montreal, and other top places around the world.  Ah… so much to do, so little time!  

All around, I find Chicago sophisticated, clean, fun, and safe (though seasoned travelers are always on their guard).  I hope you do too! 

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