Chicago City Guide

Chi-town is also a huge financial center, host to tons of conventions (and a contender for the 2016 Summer Olympics), birthplace of the skyscraper (where its “City of Big Shoulders” nickname comes from) and other groundbreaking architecture, and the first to use the term jazz. After the Great Chicago Fire of 1871 (the one mythically started by Mrs. O’Leary’s cow) destroyed a third of the city and the entire central business district, Chicago underwent fierce rebuilding and growth and a wealth of public art that continues today.

The town is made up of four main sections: Downtown (containing the Loop and financial center), the North Side (the most densely populated residential section of the city, dotted with high-rises along the lakefront, as well as Lincoln Park and River North, with its many art galleries), the South Side, and the West Side.

Culture oozes from every nook and cranny, from mad-fab theaters that actors ache to work in (Second City, Steppenwolf, the Goodman), great Chicago blues and gospel, and some of the best food on the planet. (So remind us: why don’t we live there? Oh, right. Winter. Gotcha.)

Why not upscale-shop till you drop along the Magnificent Mile stretch of North Michigan Avenue, with its classy stores, restaurants, office buildings, and hotels, as well as State Street, the bustling "main street," alive with energy (and shops, of course), made famous by the popular 1922 song "Chicago."

Bucktown/Wicker Park boasts more artists than any other area in the Midwest, including an artist colony called Gallery Point. Remnants of a historic, quainter time are evident in century-old buildings and cobblestone paths, tho it’s clearly an upcoming area with a hipster vibe … Damen Avenue’s the main drag (and home to Marc Jacobs and native daughter "http://www.cynthiarowley.com/content/location)">Cynthia Rowley , and it seems every street has its own local bar, plus tons of clubs, posh eateries, and shopping ops.

Going for glam? Head for the Gold Coast on North Lake Shore Drive, the ne plus ultra of posh pulchritude with its high-end boutiques, designer studios, and places where if you have to ask, you can’t afford it.

Want more of a scene? In Lincoln Park, you’ll find some of the city's trendiest shops, bars, and theaters (Steppenwolf among them), as well as boutiques and retailers like Restoration Hardware, lululemon, Barneys Co-Op, Betsey Johnson, L’Occitane, R.E.I., and Benetton, to name just a few. Armitage, Belmont, and Southport are fantastic shopping streets.

Meanwhile, the former hippie haven that’s Old Town is now home to upscale cottages and row houses, as well as the famed Second City improv troupe and lots of shops, bars, and eateries.

But still hankering for fabulous one-stop centers with scads of choices? 900 North Michigan Shops, on the north end of Magnificent Mile, boasts 450,000 square feet, 7 levels, and 70-plus luxury shops like Bloomie's, Gucci, Williams-Sonoma, and J. Crew. (900 N. Michigan Ave., Chicago, IL 60611; 312-915-3916) … Just don’t confuse this glitzy mall with also-glitzy The Shops at North Bridge -- 9 city blocks, 50 specialty shops, 20 restaurants, and 5 hotels, anchored by Nordstrom and accessorized by myriad other brand names like Sephora, Lucky, LEGO, Armani, Vuitton. (520 N. Michigan Ave., Chicago, IL 60611; 312-327-2300).

And that’s not all. At the top of the Magnificent Mile, 8-level Water Tower Place features more than 100 stores and a clutch of restaurants in its atrium palace. Shop Macy's, Nine West, Banana Republic, and Forever 21, among others. (835 N. Michigan Ave, Chicago, IL 60611; 312-440-3166)

Going for with-it and eco-friendly? Jump right into lively, colorful eco-lifestyle A Cooler Planet in Roscoe Village, plying fair-trade, certified organic, U.S.-made products: skin care, soap (ixnay on plastic wrappings), clothing, organic bed and bath linens, rubber shoes (from recycled tires). Wholly fun for a way-whole earth. And with every purchase, the owner-sisters plant a tree somewhere it’s needed. (2211 W. Roscoe St., Chicago, IL; 773-248-1110) … Then 300 designers + cool owners = a colorful conglomeration of crafts, clothes, cards, creatures, and lots more from local artisans at Renegade Handmade, (1924 W. Division St., Chicago, IL; 773-227-2707).

For hip duds for a song, check out Fox’s, where Chi-towners flock for designer fashion, good quality, and bargain prices. (2150 N. Halsted, Chicago, IL 60614; 773-281-0700) … Also Never Mind, for super-endearing -- and cheap—clothes and accessories. (953 W. Belmont Ave., Chicago, IL 60657; 773-472-4922)

Tons of vintage and consignment, too ... Start with Clothes Optional, a brilliantly well stocked vintage-clothing place that boasts passionate fans and a fab owl collection. (2918 N. Clark St; Chicago, IL 60657; 773-296-6630) … Friendly Buy Choice always has a fresh pot of coffee and a congenial group of shoppers at this consignment shop; owner Cathy’s sweet, irreverent sister, Claire, often helps out. (3860 N. Lincoln Ave., Chicago, IL 60613-3543; 773-296-4525) … Savvy Seconds and 1sts consignment store run by a terrific mother-and-daughter team makes up in great, hip clothes, shoes, and accessories what it lacks in spiffy location. (2707 W. Lawrence Ave., Chicago, IL 60625; 773-828-4201)

Ragstock is the go-to for cheap and trendy, fun and vintage items for the emo set. Scouts tell us American Apparel recently moved in across the street (but shhhhh, they say almost everything AA has, Ragstock has for 1/4 the price). (Ragstock: 812 W. Belmont Ave., Chicago, IL 60657; 773-868-9263; also 1433 Milwaukee Ave., Chicago, IL 60622; 773-486-1783)

Finally, let’s not overlook a noble standby: the Gap on Broadway is also noteworthy -- small enough to be manageable, but big enough to have a great selection (especially on sale stuff!). (3216 N. Broadway Ave., Chicago, IL 60657; 773-929-4085)

Feet starting to ache from all your wanderings? Time for new shoes! Head for the original Niketown, where it all began -- basketball heaven. You’ll find every shoe you can imagine for the sport, plus a 5th floor court to take your new puppies up to for a trial run. (669 N. Michigan Ave., Chicago, IL 60611; 312-642-6363) … Another option, Alamo Shoes, offers everything from come-catch-me stilettos to dorky sneaks, in every possible size, and for the whole family. (5321 N. Clark St., Chicago, IL 60640; 773-784-8936) … And then there’s Lori's Shoes, “The Sole of Chicago” for sure – a way-popular destination with a ginormous selection of what every woman really obsesses about, and at reasonable prices. (824 W. Armitage Ave., Chicago, IL 60614; 773-281-5655)

Old but never outdated: Lincoln Antique Mall offers 60 dealers, 11,000 sq. ft. of antiques – Victoriana, Mission, mid-century; jewelry, furniture, collectibles. (3115 W. Irving Park Rd., Chicago, IL 60618; 773-604-4700) … On a different scale is Brownstone Antiques, a happy, crushed cacophony of antiques, collectibles, and buried treasure to dig through; small-town flea market with prices to match (and you’re in the Big City). Jump on anything you like at this Andersonville gem, ‘cause it’ll be gone before you can ask Do you deliver (and they do). (5234 N. Clark St., Chicago, Il 60640; 773-878-9800)

Something else entirely: American Girl Place We’re talking, OMG, the flagship brick-and mortar for all fresh-faced lassies’ fantasies -- and if you haven’t a clue what we mean, you probably don’t need to come here. But if you have a 5- to 12-year-old girl in your life and don’t step into this cradle of civilization for historical dolls you can custom order to resemble their owner, plus choose some duds to go with them, well, you’ll all be missing out. (835 N. Michigan Ave., Chicago, IL 60611; 877-247-5223) … And on a completely different order of magnitude, there’s Colletti Gallery, with its vintage and antique posters (Buffalo Bill, Barnum & Bailey, anyone?), plus elegant decorative arts and artifacts, from the Belle Époque to Art Deco. Polished and perfectly posh. (67 E. Oak St., Chicago, IL 60611; 312-664-6767)

Closer to Home: CB2 delivers awesome cutting-edge housewares (think Crate & Barrel gone funky and trendy). And it’s right next to Trader Joe's. (CB2: 3757 N. Lincoln Ave., Chicago, IL 60613; 773-755-3900) …The Wooden Spoon dishes up high-quality gourmet kitchenware for the famished, the fanatic, or mere food fans and home chefs; cooking classes too, natch. (5047 N. Clark St., Chicago, IL 60640; 773-293-3190) … And the Unique Boutique not-for-profit marketplace represents local artisans and crafters—scoop up jewelry, gifts, quilts, soap, ceramics, more, at way-reasonable prices. (839 S. Oak Park Ave., Oak Park, IL 60304; 708-848-4693‎).

Women and Children First Book Store -- find a best seller or obscure resource in a true independent bookstore with great, helpful staff, deep sense of community, in the terrific Andersonville neighborhood. (5233 N. Clark St., Chicago, IL 60640; 773-769-9299) … The Book Cellar, another notable book store, locally owned, is perfect for book groups with their tables, food, and wine, along with a great selection of tomes and local authors. (4736 N. Lincoln Ave., Chicago, IL 60625; 773-293-2665)

And then there’s the Meatloaf Bakery Can you stand it? The city once known as Meat Packer to the World now has a store selling nothing but this comfort food (are you listening, L.A.?) with myriad variations on the theme, including salmon, veggie, and something related to bacon cheeseburgers, and in sizes ranging from bite bits and cupcakes to grownup loaves (and yes, there’re taters, too). (2464 N. Clark St., Chicago, IL; 773-698-6667) … Not to mention the Twisted Sister Bakery. Oh God. Whatever you do, shield your eyes from their website photos, but if you happen to be in Old Town and happen to be passing by the shop…well, we’re not responsible for what happens next. Really. (1543 N. Wells St., Chicago, IL 60610; 312-932-1128)

Goddess and Grocer sells handmade chocolates, a wide range of specialty cheeses, and fresh meats, plus holiday packages, picnics (5 E. Delaware Pl., Chicago, IL 60611; 312-896-2600) … Fox and Obel is lauded for delicious gourmet food, a world market, lots of specialty ingredients. Not cheap, but worth every penny, and they often do cool chef demos. (401 E. Illinois, Chicago IL 60611; 312-410-7301)

Spirited Stuff: Brand-new, homey Noble Grape purveys biodynamic, sustainable varietals, boutique wines from U.S. and abroad, artisanal brews, plus the other usual suspects (champagne, sake, port, and the hard stuff). (802 N. Bishop St., at Chicago Ave., Chicago, IL 60642; 312-846-1204) … Locals, meanwhile, swear by Kafka Wine as one of the best of its kind in the city—250 wines, most under $15, all delish. Cheap, easy, fun, they say.

The Truly Hard Stuff: Voges Haut-Chocolat. Can you wrap your mind around a milk chocolate bacon bar? Chocolate mushroom bar? How about exotic truffles like the Absinthe, the Budapest (mitt paprika), or the Black Pearl (ginger, wasabi, sesame seeds)? This place is local -- and maybe a little loco -- but people are gaga about this brilliant boutique, and you can understand why. (2 locations: 520 N. Michigan Ave. in Northbridge Mall, 312-644-9450; 951 W. Armitage Ave., Chicago, IL 60614; 773-296-9866) … The Fudge Pot Fudge, toffee, candy apples, etc. made in full view. Get a personalized lollipop, one of 1,000 chocolate molded items in every shape imaginable, or a custom mold or logo. (1532 N. Wells St., Chicago, IL 60610; 312-943-1777)

And from the sublime to the more mundane (but no less sublime), don’t even think about leaving Chicago without stopping in at Potbelly's for yummy toasty sandwiches from this local chain that denizens swear by; fast, but not technically fast food, if you know what we mean.