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From major department stores to chic designer boutiques, Chicago's boulevards and tree-lined streets are a haven for serious shoppers. Thanks to the city's convenient public transport, it couldn't be easier to get from one unique neighbourhood to another. CTA trains and buses run regularly, and cabs are there for the hailing on virtually every corner.

Want to shop like a pro? Then book a shopping tour designed by Chicago experts who guide you to shopping destinations based on your individual style.


Bookable Shopping Tours

Heather Kenny - A successful fashion journalist and regular contributor on shopping and style to many high-profile Chicago publications, Heather Kenny uses her insider knowledge of the city's clothing and accessories boutiques to serve as your guide to the best shopping in the city and its nearby suburbs.

SeeMore Shopping Tours - SeeMore Shopping will take you to some of our favourite fashion destinations. These locally-owned boutiques and Chicago designer showrooms are truly hidden treasures located off the Magnificent Mile.

Chicago ShopWalk - It is ShopWalk's mission to take you to all the hard-to-find boutiques that you won't find back home or on the Magnificent Mile. Tours are guided, so you can walk the streets without a map and free your hands for shopping!

Urban Shopping Tours - Tour Chicago's greatest boutiques. Spend time in the vibrant neighbourhoods and uncover fashion only a savvy local would know.

Chicago Premium Outlets - Just beyond Chicago is a shoppers' paradise. Here you will find an unparalleled collection of 120 designer and name brand stores offering savings of 25% - 65% every day. Book your exclusive transportation with Gray Line and save your energy for shopping!

Immerse yourself in our Virtual Visitor Page.
Macy's Visitor Savings Pass Voucher
Macy's on State Street is the 2nd largest department store in the world. Shop, dine, tour, meet and experience a tradition for generations of Chicagoans. Download your Visitor Savings Pass Voucher now.
Fashion Coupons Discover money-saving coupons for neighbourhood stores throughout Chicago.
Oprah’s Closet opened in 2008 and features a wardrobe full of items once worn or treasured by Oprah for sale. All proceeds go to Oprah’s angel Network charity. Monday is the best day to shop the store – the new merchandise arrives!
To learn more about Chicago designers and boutiques, view suggested shopping itineraries, and find out about upcoming runway shows and fashion events.
Clothing Conversion Chart

Don't know what size to buy? Download this useful guide.

Upscale Shopping at Discount Prices

Planning to shop on the Magnificent Mile? Then be sure to get your Exclusively 900 Card to receive special savings and incentives at The 900 Shops on Michigan Avenue.

It's All About the Premier Perks!

Visit the Water Tower Place concierge desk located in the Michigan Avenue lobby to receive your Premier Perks, offering more than 50 exclusive savings and complimentary services throughout the center, including Macy’s and American Girl Place. Plus, receive a signature Water Tower Place gift with minimum purchase.

North Bridge

Present a passport or hotel room key at Westfield North Bridge Concierge Services to receive your complimentary North Bridge VIP Savings Card featuring shopping, dining and entertainment savings at participating merchants.

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