Where to Find the Best Shopping in Chicago

Posted by Lexington Square

All of the world’s well-known cities have their famous shopping districts where people flock to part with untold sums of money. Depending on who you’re talking to, and where they’re from, opinions vary wildly on where the best shopping can be found. But, you’d be hard-pressed – no matter who you’re speaking to – to find a better city to spend your money in than Chicago. It’s not called the Magnificent Mile for nothing!

The Magnificent Mile is the fanciful name given to the mile-long stretch of North Michigan Avenue that runs from Oak Street to the Chicago River. Containing some of the world’s preeminent shopping destinations, the Magnificent Mile is part New York’s Fifth Avenue, part Beverly Hills’ Rodeo Drive, and all Chicago. In many ways, it can be seen as the beating heart of the city with crowds mingling happily throughout the year. We’ll discuss a few other shopping hotspots, but, for now, that’s our destination.

North Michigan Avenue

This is our starting point – the intersection of North Michigan Avenue and Oak Street. You can find everything here from designer stores to well-known chains. The first place to go is the Drake Hotel. That’s where you’ll find Danish silversmith Georg Jensen’s silver and gold earrings, brooches, watches, and more. The Drake also houses the iconic Chanel with their distinctive line of cosmetics, clothing, and costume jewelry.

Upon exiting the Drake Hotel, the next place to visit is one block south. That’s the location of Louis Vuitton with their trendy handbags and monogrammed luggage. Across the street from Louis Vuitton, under the shade of the Hancock Building, you’ll find a perfect place for your first rest stop. The Fourth Presbyterian Church is a Gothic masterpiece with flower-filled gardens where you can relax and catch your breath before continuing.

Once you’ve caught your breath, you’ll probably notice a fair amount of bright red bags in the hands of mothers and daughters as they pass. They’ve all come from building their own dolls at American Girl Place, one of Chicago’s most popular attractions, located in Water Tower Place Mall. There are several incredible malls located on the Magnificent Mile and each of them contains many more shops and eateries. A few of them even span an entire city block!

When you walk out of Water Tower Place, you’ll be looking directly at the Park Hyatt Hotel. That’s the home of the ultra-chic Giorgio Armani where high-fashion minimalism is all the rage. If you’re feeling dizzy from all of the price tags, you can head across the street to Hershey’s Chocolate World Chicago. You’re sure to find something there that will put a smile on your face – not to mention sugar to fuel the rest of your shopping adventure!

The next block has a definite New York feel thanks to the four-story mansion that serves as home to the world’s largest Polo Ralph Lauren Store. No matter what you’re looking for, this Polo palace is sure to have it in stock – in every color imaginable. The Fifth Avenue vibe continues at world-famous Tiffany & Co. where you’ll find their signature line of jewels, clocks, and home accessories.

Just a few doors down from Tiffany & Co., you’ll find ultra, high-end department store Neiman Marcus with all of their signature clothing, jewelry, and over-the-top gift ideas. Niketown, the birthplace of retail store as entertainment destination, is right next door. You can find every shoe they’ve ever made (or very nearly) in a multitude of colors and prices. Through the windows of Niketown, you’ll see an odd, barrel-shaped building across the street. That’s the flagship location for Crate & Barrel, a Chicago original, where you’ll find glassware, dishes, cookware, and more kitchen gadgets that you could ever possibly use. The two top floors are dedicated entirely to furniture.

The final leg of our North Michigan Avenue excursion leads us to the iconic beige plaid of Burberry where you’ll find those colors draped across everything from purses to shoes. They have a line of dog clothes that make the perfect souvenir – and won’t break the bank! La Perla, the Italian lingerie designer, is next door if you’re looking for something romantic – and in the price range of a mortgage payment. Finally, you’ve arrived at a true Chicago original, Garret’s Popcorn, where you’ll find locals and tourists alike waiting in line for a taste of their heavenly caramel corn. It’s well worth the long blocks you walked while shopping!

Nearby Oak Street

If there’s one thing you can count on in Chicago, it’s that if a store has an Oak Street address it’s sure to be expensive. It’s probably a good thing that there aren’t too many shops on Oak – the whole shopping district is only about a block long – otherwise the Magnificent Mile might have a serious challenge to the Chicago shopping throne. You can find the shops situated at the northern end of the Magnificent Mile where Michigan Avenue ends and Lake Shore Drive begins.

With much smaller, more intimate shops than North Michigan Avenue, most tucked into charming, converted townhomes, there’s a much quieter, serene feeling here compared to the bustle of the Magnificent Mile. It’s amid this serenity that you’ll find Italian shoemaker Tod’sfamous for their pricey and luxurious driving shoes. Kate Spade is up next with shoes, handbags, stationery, and their Jack Spade line of men’s accessories. Possibly the most expensive items found on this very expensive street are at Hermès of Paris.

Two incredible linen stores, Pratesi and Frette, supply the finest hotels in Chicago and boast thread counts for prices that most people equate with rent or car payments. Heavyweight Italian designer Prada boasts three floors of their signature handbags and accessories. Leaving Prada, you’ll arrive at stylish department store Barney’s New York where you’ll find everything you’d expect to find in one of the world’s great chain stores.

Before leaving Oak Street for the next stop on your Chicago shopping tour, you’ve got to stop by Bravco, an out-of-place, crowded little drugstore. In a place where expensive is the norm, Bravco offers hot, name-brand cosmetics and hair products that the salons sell, but at a third of the price. It’s the go-to shop for Chicago makeup artists and stylists and should not be missed!

State & the Loop

The Loop in Chicago is famous for its name and the incredible architecture you can find there. Yet, along State Street, from Randolph Street southward to Congress Parkway, you can find some interesting bargains and one spectacular grand department store in less than a mile. The jewel in State Street’s crown is Macy’s at State Street. Once known as Marshall Field’s, the store is not only one of the largest department stores in the entire world, but one of Chicago’s most beloved landmarks as well. Boasting the largest Tiffany & Co. glass mosaic dome in the United States, Macy’s has everything you imagine when you think of the grand old department stores of the past. If you’re in town for the holidays make sure to stop by to look at the breathtaking window displays and have lunch at the world-famous Walnut Room under the Great Tree inside!

When you’re finished in Macy’s, take some time to bargain shop in the discount stores clustered on State Street. Take your pick from Nordstrom Rack, T.J. Maxx, and many more. If you have the time, and the patience, you can find some incredible deals. Just a few blocks away on Wabash Avenue you can find Jewelers’ Row. While it’s not the Diamond District in Manhattan, there are more precious gemstones here than just about anywhere else on Earth. Stop by the building at 5 Wabash Avenue to visit some of the most amazing jewelry dealers in the world.

The Shops at River North

The Shops in the River North neighborhood, the primary art gallery district in Chicago, are located just west of the Magnificent Mile. There are shops and boutiques of all kinds found along this thoroughfare, but the home-design stores are the real reason for coming. The best starting point for this shopping extravaganza is the intersection of Kinzie Street and Wells Street, and concludes once you’ve reached Chicago Avenue.

Your first stop has to be Manifesto. They offer imported furniture from all over Europe, with a focus on Italian leather, and craft some of the most mind-bending pieces of custom furniture you can imagine. Next up is Orange Skin – a boutique offering truly unique decorating accents. As soon as you walk out of Orange Skin, your eyes will be drwn to the windows of the most amazing lighting store on the planetLightology. With more than 400 manufacturers represented in their collection, there isn’t a lamp or lighting fixture you can name that they don’t have in stock or can lay their hands on. It’s the only lighting store you’ll ever need, or even want to visit for that matter.

Before you leave River North, you should take some time to check out the Merchandise Mart. As the world’s largest commercial building, the interior is filled with showrooms dedicated to professional designers and actually functions as a business. While not open for public shopping, it does offer tours for $12 on Fridays that are worth taking if you love shopping and design.

Shopping In Lombard and Elmhurst

When it comes to great shopping, you don’t have to travel all the way into the city. There are several great shopping venues located right in Lombard. The first and one of the most popular is the Yorktown Center located in the heart of the Western suburbs of Chicago. This two-level shopping center boasts over 150 stores and 20 restaurants.

The other major shopping center near our Lombard and Elmhurst locations is the Oakbrook Center. This outdoor shopping mall offers shoppers a selection of over 160 specialty stores and unique dining experiences. New in 2017 is a 14,000 square foot dining destination called District.

A Few Other Shopping Ideas: Armitage Avenue

Nestled in between Old Town and Lincoln Park, Armitage Avenue is quickly becoming a premier shopping destination in Chicago. Starting at the Armitage stop on the Brown Line, you can shop your way down to Halsted Street before cutting the corner onto Webster Street. This half-hour stroll includes beauty shops, home-design stores, trendy clothing boutiques, and one-of-a-kind gift shops carrying everything under the sun. The highlights here include Chicago-native Cynthia Rowley’s ultra-hip boutique, Art Effecta gift shop like no other, and, for those who love bargains, Lori’s Designer Shoes and The Second Child.

A Few Other Shopping Ideas: Southport Avenue

Right near Wrigley Field, you can find great shopping and excellent food intermingled throughout a leisurely half-hour stroll. Beginning at the Southport Brown Line stop and heading north toward Grace Street, you’ll find a seemingly endless procession of bars, cafes, boutiques, and shops of all kinds. Make sure to stop by Krista K for a glimpse of up-and-coming designers’ pieces you won’t find anywhere else!

A Few Other Shopping Ideas: Wicker Park

As is often the case, gentrification of a neighborhood leads to an influx of businesses bent on capitalizing off of the new money being invested in the surrounding area. Wicker Park is one such place. With neighborhood businesses spanning 50 years and more mixed into the new shops and boutiques that have sprung up since the neighborhood began changing. It’s an interesting mix to say the least. You have antique furniture stores, chic boutiques, discount chains, religious iconography stores, and eclectic galleries lined up one after another. Your best starting point is the Damen stop on the Blue Line. When you get to Armitage Avenue, if you have the time, you can continue down Milwaukee Avenue for even more shopping!

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