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Chicago: A Shopper's Guide

By Helen Brown

Nobody wants to be seen as materialistic and shallow, right? So before I start writing a materialistic and shallow story about shopping in Chicago, I feel the need to point out that this is a city that has it all -- galleries, museums, shows, fascinating tours, nightlife, culture, history, everything the discerning traveller might be looking for. Serious things. Important things. But this is all about shopping.


Since the shopping venues in Chicago are borderline infinite and I couldn't begin to know them all, I'm just going to tell you about the ones I do know, and how I know them.
We are five friends who love to shop. (So, okay, I guess that makes us a little materialistic. But I won't admit to shallow, since we all also do other, serious and important, things.) Every summer for the last several years we have spent a food-, wine-, and giggle-filled extended weekend in the Windy City, and have honed the expedition to its essentials.
If that concept interests you, here's what to do: First, pick your dates. We have found that the best summer sales run right after the July 4th holiday, and that discounts in some stores are deeper on the weekends than weekdays. Then, pick your hotel -- on, or just off, the Magnificent Mile. The Magnificent Mile is a stretch of North Michigan Avenue, right near downtown, that is without doubt one of the most fun destinations on the continent. For shoppers, anyway, but it's possible there might be some other things to do, too. Packed with happy strolling tourists both day and evening, it is the mother lode of stores, big, small, high-end, low-end; eateries, big, small, high-end, low-end; and hotels, big, small, high-end... though sadly coming up a bit short on the low-end end.
But it is worth paying a bit extra to be Right There. With a hotel this central, it is possible to spend the entire stay without ever climbing into a cab or a train. And I personally kind of enjoy city noises, even at night.
Before leaving home, be sure to check the web for coupons to print. Macy's, in particular, has an almost continuous flow of coupons. They also offer a discount to out-of-town visitors, so be sure to bring some ID with an address.
Also before leaving home, avid foodies looking for very special dining experiences should do their restaurant research and reserving ahead of time, as tables can be hard to get at the most popular spots.
Now, the schedule. If arriving at O'Hare (preferably early in the morning), hop in a cab and take the approximately $60 to $80 (depending on traffic) ride to your hotel. We always arrive long before check-in, but go there first to stow our luggage.
Our next step, every time, is to leave the Mile (just this once), and walk straight south on Michigan Ave. to the big Macy's store on N. State St. in "the Loop", Chicago's central business district. At about 2.5 km (depending on hotel location), it's quite a hike, but energy is still high on the first day. This nine level, early 20th century, old style department store was Marshall Field's flagship store until 2005, and many Chicagoans have yet to forgive Macy's for the takeover.
As it happens, we generally arrive in that area hungry, and as it happens, there are a couple of fabulous places to eat, right nearby. If it is early, one of the best breakfast spots in the world is on E. Randolph St., just a block from the store -- Wildberry Pancakes and Cafe. There can be quite a wait to get in, specially on weekends, but it's worth it. And if it is closer to lunch time, just a few steps from Wildberry is Tavern on the Park, hip and trendy and crowded and yummy.
Perfect. Five women with full stomachs and high expectations can make the enormous Macy's last a good three to four hours, easy. With great selection, great sale prices, and pleasant staff, it is a wonderful way to kick off the getaway. We come away with many bags.
The walk back is a little slower, and has even been known to happen in a cab. It always involves a stop at the Michigan Ave. Walgreens, about midway in the Mile, for cheap wine and junk food, which we are now ready for. Then, check in, settle in, and show and tell, so we can compare and admire everyone's treasures and bargains.
Now dinner. Preferences for restaurants are so individual, and the number of great places to choose from in Chicago is so huge, that I hesitate to make specific recommendations. That first evening we are pretty much exhausted, so our main criterion is that it be close by. The second (and third, if there is one) evenings we are more particular, and will have made online choices and bookings in advance. Not once have we been disappointed.
Now for the Magnificent Mile. If there are two shopping days left, the sensible thing is to do the south end one day, and the north end the other. The street is not limited to its own storefronts. Behind the facades are three enormous multi-level malls, The Shops at Northbridge, Watertower Place, and 900 North Michigan Shops. There are also more stores worth looking into on the cross streets.
I am a particular fan of the big Marshalls and TJ Maxx discount stores just around the corner on Ontario St. From that you might be able to guess that I don't spend a lot of time at the much more upscale Saks or Bloomingdales -- but they are both there if you want them. Almost everything is there. Have at it.
This is where I leave you. Power shoppers would be advised to do some preparatory online research, because there is so much territory to cover; browsers will have a wonderful time just wandering.
One last thing. No one can ever leave this city without buying some Garrett popcorn, "a Chicago tradition since 1949". We get ours at the airport, but there is also a kiosk at Watertower Place, and further south, on Ontario St. There are several flavours, but the one to get is the Garret Mix, a combination of CheeseCorn and CaramelCrisp. My sizeable airport-bought bag rarely makes it home. Oh. And bring an umbrella.