State Street & The Loop

This was Chicago's first great shopping district -- by World War I, seven of the largest and most lavish department stores in the world were competing for shoppers' loyalties along a half-mile stretch between Randolph Street and Congress Parkway. The area has now been eclipsed by Michigan Avenue, and State Street now is lined with discount stores and fast-food outlets. But it's still worth visiting because of the two grand old department stores that remain: Marshall Field & Co., 111 N. State St., at Randolph Street (tel. 312/781-1000); and Carson Pirie Scott & Co., a few blocks south, at 1 S. State St., at the corner of Madison Street (tel. 312/641-7000). Both buildings are city landmarks and attractions in themselves. Architecturally speaking, the Louis Sullivan-designed Carson's is the more celebrated of the two; however, Field's State Street store remains one of the world's largest, occupying an entire city block and featuring the largest Tiffany glass mosaic dome in the United States. If you're in Chicago between Thanksgiving and New Year's, a visit to Marshall Field's to see the holiday windows and to have lunch under the Great Tree in the Walnut Room is in keeping with local tradition.

Although State Street has not recaptured the glamour of decades past, it manages to draw crowds of loyal customers from the Loop's office towers and Chicagoans turned off by Michigan Avenue's snob factor. There's no better example of the street's revival than the 2001 opening of a new Sears store (tel. 312/373-6000) at the corner of State and Madison streets and a large Old Navy store at Washington and State streets (tel. 312/551-0522).

Jewelers' Row--It's not quite as impressive as the Big Apple's diamond district, but Chicago's own "Jewelers' Row" is certainly worth a detour for rock hunters. Half a dozen high-rises along the Wabash Avenue El tracks in the heart of the Loop service the wholesale trade, but the one at 5 S. Wabash Ave. opens its doors to customers off the street. There's a mall-like retail space on the ground floor, crammed with tiny booths manned by smooth-talking reps hawking their wares, and you can grab a map here for a self-guided tour of the rest of the building's tenants. It's quite an experience because many are closet-size cubbyholes with hunched-over geezers who look as if they've been eyeballing solitaire and marquise cuts since the Roosevelt administration -- Teddy, that is.

River North

Along with becoming Chicago's primary art-gallery district, River North -- the area west of the Magnificent Mile and north of the Chicago River -- has attracted many interesting home-design shops, concentrated on Wells Street from Kinzie Street to Chicago Avenue. The neighborhood even has a mall of its own -- The Shops at the Mart (tel. 312/527-7990) -- in the Merchandise Mart, at Wells and Kinzie streets, with a standard collection of chain stores.

The rest of the Merchandise Mart, the world's largest commercial building, houses mostly interior design showrooms -- which are open only to professional designers. The massive complex was built in 1930 by Marshall Field & Company, and bought in 1945 by Joseph P. Kennedy (JFK's dad); the Kennedy family ran the Mart until the late 1990s. The only way for visitors to get a sense of the whole massive complex is to take a public tour, usually offered Fridays at 1pm ($10 adults; tel. 312/527-7762).

Not all of the furniture trade in Chicago is confined to the Merchandise Mart. In River North, you'll find Manifesto, 755 N. Wells St., at Chicago Avenue (tel. 312/664-0733), offering custom-designed furniture, as well as imports from Italy and Austria, and Mig & Tig, 549 N. Wells St., at Ohio Street (tel. 312/644-8277), a charming furniture and decorative-accessories shop. Sawbridge Studios, 153 W. Ohio St. (tel. 312/828-0055), between LaSalle and Wells streets, purveys exquisite handcrafted furniture, accessories, and gift items from artisans across America in a handsome, lofted, gallery-type space with exposed brick walls. Michael FitzSimmons Decorative Arts, 311 W. Superior St. (tel. 312/787-0496), is one of the top dealers anywhere for furniture and furnishings dating to the Arts and Crafts period.

Creative types will find their imaginations running wild with homemade projects at the three-level Paper Source, 232 W. Chicago Ave., at Franklin Street (tel. 312/337-0798). Artists, designers, and other paper fetishists can choose among reams of exotic and unusual paper, as well as journals, gift items, handmade wedding albums, and a roomful of fun rubber stamps.

Lincoln Park

The North Side neighborhood of Lincoln Park has a variety of unique specialty shops that make it easy to browse through this leafy, picturesque community. While many of the shops on Michigan Avenue are branches of national chains and offer few surprises, the shops and boutiques in Lincoln Park tend to be locally owned and offer unique and interesting wares. Shops are located on the primary commercial arteries running through the area, including Armitage Avenue, Webster Avenue, Halsted Street, Clark Street, and Lincoln Avenue.

Armitage Avenue -- Armitage Avenue has emerged as a shopping destination in its own right, thanks to an influx of wealthy young professionals who have settled into historic town homes on the neighboring tree-lined streets. The shops and boutiques here -- which sell everything from artisan-made apparel to offbeat gifts -- are geared toward a sophisticated, well-heeled shopper, and make for great browsing. As you stroll the area, you will feel part of a community, with neighbors greeting each other and catching up on the street corners. Most of the shops are concentrated between Halsted Street and Clybourn Avenue.

Here you'll find Urban Gardener, 1006 W. Armitage Ave. (tel. 773/477-2070), a two-story garden shop in an old Victorian row house with lovely displays of gardening books and tools, topiaries, garden furniture, and other gifts; Lori's Designer Shoes, 824 W. Armitage Ave. (tel. 773/281-5655), for a great selection of shoes at great prices; and the jaw-droppingly beautiful Tabula Tua, 1015 W. Armitage Ave. (tel. 773/525-3500), with everything you need to set the perfect table.

A number of clothing and accessories stores cater to the hip young women who live in the area. Celeste Turner, 859 W. Armitage Ave. (tel. 773/549-3390), offers sophisticated suits, dresses, and eveningwear from up-and-coming designers. Art Effect, 934 W. Armitage Ave. (tel. 773/929-3600), which bills itself as a "modern-day general store," stocks everything from cute blouses and creative jewelry to handmade picture frames, which makes for fun browsing. Bargain hunters shouldn't miss Fox's, 2150 N. Halsted St. (tel. 773/281-0700), a perennially crowded shop that offers designer clothing at a steep discount. The downside: Most clothing labels are cut out, so you might not know exactly which A-list name you're buying. But Chicago fashion insiders flock here; as I heard one woman say recently as she shopped at Fox's: "Too often, I stock up at Sak's, then find the same thing here for less." Another great stop for designer clothes at real-people prices is the consignment shop McShane's Exchange, 815 W. Armitage Ave. (tel. 773/525-0282). And don't miss the boutique of local-gal-made-good Cynthia Rowley, 808 W. Armitage Ave. (tel. 773/528-6160).

Pamper Yourself--When all that Armitage Avenue shopping gets just too exhausting, take a break at one of the beauty stores concentrated within a few blocks of each other on Halsted Street. Endo-Exo Apothecary, 2034 N. Halsted St. (tel. 773/525-0500), lined with vintage wood cabinets, is a peaceful retreat that stocks a number of specialty skin-care and make-up lines; they'll even give you a complimentary makeover. The mood is more flashy and hip at Fresh, 2040 N. Halsted St. (tel. 773/404-9776), where the sleek shelves are filled with skin treatments, at-home spa supplies, and their own line of cosmetics; test out some of the aromatic products and you'll feel instantly rejuvenated. Now that you're freshened up and made over . . . it's time to get back to shopping!

Lakeview

Shoppers will find elements of both prosperous Lincoln Park and alternative-ish Wicker Park when they're wandering along Lakeview's principal avenues.

Belmont Avenue & Clark Street -- Radiating from the intersection of Belmont Avenue and Clark Street is a string of shops catering to rebellious kids on tour from their homes in the 'burbs (the Dunkin' Donuts on the corner is often referred to as "Punkin' Donuts" in their honor).

One constant in the ever-changing youth culture has been the Alley, 858 W. Belmont Ave., at Clark Street (tel. 773/525-3180), an "alternative shopping complex" selling everything from plaster gargoyles to racks of leather jackets. It has separate shops specializing in condoms, cigars, and bondage wear.

All the latest men's (and some women's) fashion styles -- from names such as Fresh Jive, Fuct, and Diesel -- can be found under the same roof at the multiroom building housing the Aero and Untitled shops, 2707 N. Clark St. (tel. 773/404-9225). Whether you're into tight, fitted fashion or the layered, droopy-pants look, it's here. Tragically Hip, a storefront women's boutique at 931 W. Belmont Ave. (tel. 773/549-1500), next to the Belmont El train stop, has outlasted many other similar purveyors of cutting-edge women's apparel.

Or, you can get plugged into what the kids are reading at Chicago Comics, 3244 N. Clark St. (tel. 773/528-1983), the industry's 1998 pick for best comics shop in the country. Besides the usual superhero titles, you'll find lots of European and Japanese comics, along with underground books and 'zines.

Southport Avenue -- Another strip worth a stroll is the gentrified retail row along Southport Avenue, a few blocks west of Wrigley Field. With the Music Box Theater at 3733 N. Southport Ave., north of Addison Street, as its anchor, the area has an interesting mix of quirky and artsy merchants and restaurateurs. P.O.S.H., 3729 N. Southport Ave., between Waveland Avenue and Grace Street (tel. 773/529-7674), offers never-used vintage silver and commercial-grade china from European and American hotels and restaurants that make for fun, quirky tableware. A new boutique catering to hip young women with plenty of disposable income is Krista K, 3458 N. Southport Ave. (tel. 773/248-1967), which stocks hot newer designers that aren't widely available in Chicago.

Wicker Park/Bucktown

The go-go gentrification of the Wicker Park/Bucktown area has been followed by not only a rash of restaurants and bars, but also retailers with an artsy bent that reflect the neighborhood's bohemian spirit. Mixed in with old neighborhood businesses, such as discount furniture stores and religious icon purveyors, is a proliferation of antique-furniture shops, too-cool-for-school clothing boutiques, and eclectic galleries and gift emporiums.

The friendly modern-day Marco Polos at Pagoda Red, 1714 N. Damen Ave., second floor (tel. 773/235-1188), have imported beautiful (and expensive) antique furniture and art objects, including Chinese concubine beds, painted Tibetan cabinets, Burmese rolling water vessels, cast-iron lotus bowls, bronze Buddhas, and Chinese inspiration stones. The three women who opened the upscale bazaar Embelezar a few years ago at 1639 N. Damen Ave. (tel. 773/645-9705) purvey exotic merchandise from around the world, both old and new, including the famous Fortuny silk lamps -- hand-painted in Venice at the only studio allowed to reproduce the original Fortuny designs. You'll find a well-edited selection of home accessories and jewelry at Lille, 1923 W. North Ave. (tel. 773/342-0563). The airy, white space looks like an art gallery, with pieces from internationally known designers (Lulu de Kwiatkowski handbags, Christian Tortu vases) alongside plenty of quirky objects.

Hip young dudes will find everything for the well-dressed 21st-century man at Apartment Number 9, 1804 N. Damen Ave. (tel. 773/395-2999), a shop that specializes in trendy -- but not outrageous -- modern menswear. And really hip dudes should stop by Quimby's, 1854 W. North Ave. (tel. 773/342-0910), the source for every kind of obscure, alternative, and possibly offensive comic, magazine, and self-published 'zine.

Taking a Break in Wicker Park--When you're ready to rest your weary self, settle down at a local coffeehouse and soak in Wicker Park's artsy vibe. Earwax Café, 1564 N. Milwaukee Ave. (tel. 773/772-4019), attracts the jaded and pierced set with a no-frills, slightly gritty atmosphere. Filter, across the street at 1585 N. Milwaukee Ave. (tel. 773/227-4850), is a little more welcoming; comfy couches fill the main dining room, which features paintings by local artists. Both cafes are near the bustling intersection of North, Milwaukee, and Damen avenues -- the heart of Wicker Park -- and draw a steady stream of locals. It's here you'll realize that Wicker Park is really just a small town -- with cooler hair and funkier shoes.

Chic Boutiques

In the not-so-distant past, local fashion addicts fled to the coasts to shop for cutting-edge designer duds. Those days are over. Chicago has come into its own fashion-wise as a new generation of boutiques has sprung up, offering a fresh array of unique accouterments. These are some of the best.

The cozy, minimalist Chasalla boutique, 70 E. Oak St. (tel. 312/640-1940), specializes in clothing from designers' younger, slightly more-affordable labels, including Versace's Versus, D&G, Hugo Red Label, Cinque, and GFF Gianfranco Ferre.

Just around the corner from chic Oak Street is the newest fashionista haven, Ikram, 873 Rush St. (tel. 312/587-1000). Run by Ikram Goldman, a former saleswoman at well-known women's clothing store Ultimo, the shop stocks all the big names, from Valentino to Yves St. Laurent -- and whatever else Vogue has declared "hot" for the season. But tucked among the high-priced pieces are jewelry, stationery, and decorative accessories that give the place a personal touch.

Clever Alice, 2248 N. Clark St. (tel. 773/665-0555), used to be Lincoln Park's best-kept secret, when it was tucked away on the lower level of a town house. Now that the store has moved upstairs, with a bright, airy interior and large display windows, it's attracting more attention. Loyal fans love the body-conscious, European-inspired clothing and fun accessories.

With white-hot designers including Tocca, Plein Sud, St. Vincent, and Barbara Bui Initials filling the racks, it's no wonder that business is booming at Jolie Joli, 2131 N. Southport Ave. (tel. 773/327-4917). Located in an uninteresting stretch near the Clybourn Corridor but well worth seeking out, the boutique offers killer men's and women's wear by NY Industrie, playful frocks by Shoshanna, and racks of other garb by hard-to-find labels.

Wicker Park's p45, 1643 N. Damen Ave. (tel. 773/862-4523), is a gold mine of urbane and cutting-edge fashion for men and women. Word about the store's unique mix of hip national labels (Michelle Mason, Rebecca Danenberg, Colovos, Catherine, and M Collection) and local designers (Amy Zoller, Urban Armor by Sandy Neal, and Regan Wood) has spread far and wide since the boutique's 1997 opening. Innovative fashions from emerging young designers are draped all over this slick lofted space.

Browsing Robin Richman, 2108 N. Damen Ave. (tel. 773/278-6150), feels more like poking around a big, antiques-filled closet than shopping for threads in Bucktown. The walls of this tiny storefront are adorned with balls of string, vintage diaries, and artful handmade wire hangers. While Richman carries a small assortment of men's and women's separates (mostly loose, unstructured pieces), the big draw here is her exquisite sweaters.

Very few retail outlets can successfully mix the haute designs of a British-style queen like Vivienne Westwood with quirky skater T's and street-savvy cargo pants, but Nigeria native Obi Nwazota has done just that at his spare Wicker Park boutique, Softcore, 1420 N. Milwaukee Ave. (tel. 773/276-7616). The 31-year-old architect and designer's sense of style is urban, nonconformist, and no-holds-barred.

Kim Hiley, the owner of Tribeca, 2480 1/2 N. Lincoln Ave. (tel. 773/528-5958), describes her style as "the kind of clothes you might wear on a date." While she doesn't eschew the essential blacks and grays, her racks are lined with pastels, oranges, teals, and flowery, exotic patterns. The store is bright, cutesy, and essentially feminine, catering more to the style sensibilities of corporate Lincoln Park 20-somethings than hipster Wicker Park club hoppers. Hiley recently opened a second location at 1013 W. Armitage Ave. (tel. 773/296-2997).

Lincoln Park 20- and 30-somethings flock to Shopgirl, 1206 W. Webster Ave. (tel. 773/935-SHOP) to pick up the latest looks from trendy lines such as Trina Turk and Theory. It's a girly gathering place (pink walls, glittery chandeliers) with three-digit price tags, but it still has the feel of a neighborhood hangout, thanks to the friendly staff.