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!