Sorta like the hairdresser school of restaurants. Lettuce Entertain You concept employs up-and-comer chefs for several-week stints, gives them full free rein. Space could have been afterthought, but actually intimate and even a touch romantic – with warm woods, low lighting and charmingly mismatched furnishings. For epicures with adventurous streak.


Only a genius could create an upscale drugstore that focuses solely on makeup, fragrances, and skincare products. Don’t be shy about testing classics like Chanel No. 5. Or Calvin Klein’s Obsession for men. The extremely neat space holds a deceptively large assortment of goodies. Like eye shadow, mascara, and foundation from major players including Dior and Smashbox. But makeup can be murder in the wrong hands. It’s worth the wait for face time with one of the helpful reps.

Barneys Co-Op

Of the moment, young, emerging-designer wares retailed in open warehouse spaces with “downtown vibe.” Casual apparel and accessories, full denim bar. Funky jewelry, pop tart/movie star sunglasses, designer “it” bags, and cutting-edge footwear to turn any ensemble into a talked-about look. More affordable options than at the Barneys flagship stores, same attentive service.

MAC Cosmetics

Rock star hues, luscious skin care line, lightweight Mineralize collection, and sheer bronzers top make-up pro wish lists. Retail space is smartly organized by color stories, and the often-eccentric MAC Artists are more than willing to help in the selection process. Beware of lingering too long, as you’ll find another must-have item every time you turn around. So much screaming fun to pop in to get a new look real quick.

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie. Downtown model-wannabe party kids stooped to employment in the hopes of being featured, scantily clad and compromisingly positioned, in their ubiquitous adverts. With the novelty worn off (and security tightened), the store’s become the alternative next generation of Gap: you can’t walk into a bar without seeing someone sportily sporting the cheaply-priced, sturdy duds. Started questionable trends from the sweatband headband to glittery leggings. Recently started selling upmarket California-inspired vintage too.


Owner Kaveri Satpathy aims to offer something a little different than the basic boutique offerings. Drawing inspiration from the London shopping districts of her youth, Kaveri attempts to emulate the kind of shop you might find in Notting Hill: classic designs with simple twists. Names like Earnest Sewn, Tory Burch, Tocca, and Generra dominate the hangers and are easy to focus on, given the warm welcome environment.

Barker and Meowsky

The full name of this LP pet boutique, Barker & Meowsky: A Paw Firm, pleases us almost as much as the plethora of fun pet products available inside. Custom-made dog beds, all kinds of chi-chi and not-so-fancy carriers, an extensive collar collection and a delightful array of toys make browsing fun. And of course, it being Chicago, there’s a fantastic collection of winter coats for your four-legged friends.

Weddings 826

Originally concepted as a one-stop shop for all things wedding, this boutique has since evolved into an off-the-rack bridal gown store. Located in a little brownstone building, space is charming and intimate, making every bride-to-be feel extra special as she sips champagne and tries on gowns by over 100 different designers. Store helpers are passionate about what they do and suggest fun accessories like tiaras, garters and bridal flip flops.

McShane’s Exchange

Designer consignment shop packed to the gills with amazing finds. Filled with racks that go on seemingly for miles, shoppers browse through items like Betsey Johnson coctail dresses, Burberry coats, Gucci heels and denim by the likes of Miss Sixty and Seven. The second level is a mish-mash of maternity and clearance, and can range in quality from ultra-tailored to threadbare. If you’re looking to lighten your load, McShane’s also has a decent consigment deal for those of you with closets already busting at the seams.