3-Day Chicago Shopping Experience

Day 1 You'll See:

Michigan Avenue, downtown Chicago, IL

Day 2 You'll See:

Day 3 You'll See:

The Windy City may mess up your hair, but it won’t mess up your fashion-forward shopping and education plans, that’s for sure! An underrated fashion icon in the United States, Chicago provides some of the finest, highest quality, and most unique shopping experiences in the nation. Not only that, but it also provides great insider looks at various showrooms, designer studios, and even retail stores themselves. Get ready to get your fashion on!


Chicago Shopping Tour - There is truly no better way to start your big Chicago fashion journey than with the Chicago Shopping Tour, the tour with all the ‘access to inside knowledge on the best boutique shops in the trendy Lincoln Park neighborhood’. Your fashion-forward group will receive exclusive discounts, a VIP personal shopping stylist, and your choice or 2 or 3.5 hours of sophisticated Chicago exploration. Explore local designers and latest trends while being pampered with coffee, champagne, gift certificates, and discounts galore (be sure to take advantage of these shopping perks before you leave the city.

Giordano's - Giordano’s is a classic pizza joint in Chicago, this one iconic for its ooey-gooey stuffed crust. Giordano’s holds one of the most famous stuffed pizza, one that has evolved over 200 years of generational recipes. Here your group can relax and enjoy what thousands upon thousands have called the city’s best-stuffed pizza, the pie itself 40% bigger than any other deep dish in the city. Try the Chicken and Sausage, Artichoke and Feta, or the iconic, classic, oh-so-delicious original cheese. Trust us, we’ve Giordano’s, and you will be wanting to come back for more as soon as you get home. The best part about eating here? You will already be at your next stop, one of the most iconic Chicago shopping centers and landmarks, the Navy Pier.

Navy Pier -Built in 1916, this Chicago landmark is a shopping, eating, and sightseeing mecca for tourists and locals alike. 50 acres of attractions will greet you here, the entire pier itself an attraction and site to see. Hanging over Lake Michigan, the views alone should sell you on the place! If not the 150-foot tall Ferris wheel will, or perhaps the Crystal Gardens, the 6-story indoor atrium. Visit all the specialty shops and boutiques within, eat at Giordano’s, and even see an IMAX movie!


Magnificent Mile Morning Walking Tour - Start your second Chicago day with an early-riser walking tour, the newish yet growingly popular Magnificent Mile Morning Walking Tour. This 2-hour early morning tour allows you to ‘catch the Windy City as it wakes up’, a really unique and beautiful way to see the city streets. Beat the crowds to all of the best boutiques, showrooms, and sightseeing stops while on this tour, the entire experience giving you great insight into Chicago history, architecture, private clubs, and historic hotels, much more than just the boutique life. Meet your professional tour guide on Michigan Avenue, the Starbucks in particular, and grab a cup of coffee before setting off. Your route will include the Chicago Water Tower, Tribune Tower, Wrigley Building, Intercontinental Chicago, Magnificent Mile, Chicago Women’s Club, and your ending location, Drake Hotel.

Free Time at Magnificent Mile - After walking the route now shop the route, your  group in for a true retail therapy treat as they explore one of the most vibrant and successful commercial, residential, cultural, and tourist areas in the world, the 1 full square mile of shopping and dining in downtown Chicago known as the Magnificent Mile. This 13-block stretch is located along North Michigan Avenue, from the banks of the Chicago River on to the South. Shopping along this stretch, or even just strolling along it, is an essential ultimate Chicago experience, one of the greatest avenues of the world at the center of all that makes Chicago an international destination. This district showcases the style, flavor, entertainment, and fun of Chicago, with over 460 stores, 75 restaurants, 60 hotels, unique entertainment and attractions to match every passion and every pocket.

Hancock Tower -Known as 360 Chicago today instead of the Hancock Tower, this spot is where your group will find the ‘best views, best location, and best observation deck’. That’s a great view to scope out your next shopping adventure!! This 96-floor architectural wonder played a huge part in the development of Chicago, originally being the second tallest building in the world when built. Today 360 is the 4th tallest in the city, 33 tallest in the world.  This structure provides the most breathtaking views of downtown, Lake Michigan, and the lakefront, and 4 neighboring states, and the iconic city skyline as well.

Shops at North Bridge - Dinner and shopping all mixed into one? Yes, please! At Chicago’s famous Shops at North Bridge, you will find one of the widest selections of both retail stores and popular eateries, this entire spot consisting of 6 whole city blocks. Be sure to wear comfortable shoes, because that’s a lot of shopping to do and ground to cover! Your group will find a wide variety of stores and popular restaurants here, the base of the shopping center considered to be the flagship Nordstrom store. Aside from that, there will be 50 more retail stores, 20 restaurants, and even Chicago’s very own Italian market, Eataly. Find everything from fresh new trends to classic vintage styles with stores such as Hugo Boss, Lucky Brand, Louis Vuitton, and even Microsoft.


Kinzie State Showrooms - The locally and nationally celebrated showroom facility, Kinzie State Showrooms, will start your fashionista day off right, this spot an appealing venue with a unique environment.  Kinzie was started in 2012 by a group of apparel representatives who wanted a ‘venue that would provide a comfortable and appealing space for themselves and buyers,’ the general idea that all parts of the fashion industry deserve to work comfortably. You will see such popular names as Helen Newman, Andi Mazzone, Outfit Chicago, and Fashion Lab, plus the hundreds of lines ranging from Acrobat to Zuzu. What better way to see a sustainably successful and quickly growing showroom environment?

Eataly -  When you think of shopping and high fashion your probably think of Milan and Italy, so let us take you to the next best thing; Eataly. Seen before at Shops at North Bridge,  Eataly is Mario Batali's massive Chicago outpost, a recreation of an authentic Italian market and a foodie hotspot. Find several different Italian eateries and fresh food markets within, Zagat describing this spot as an 'Upscale and interesting amusement park for Italian foods'.Try Ristorante Toscano for an exciting pop-up eatery experience, La Pizza and La Pasta for excellent Napoli and Al Dente treats, Osterra Di Eataly for wine, and of course, Birreria for craft microbrews like you'd find in Italy itself. Buon appetito!

Merchant Mart 9th Floor -The Merchandise Market is a truly excellent place to end your big Chicago journey, this building being the epitome of Chicago shopping. This popular commercial building, upon first opening in 1930, was the largest building in the world, an astounding 4 million square feet of floor space. At 340’ and 25 stories, today Merchandise Mart isn’t quite the largest building in the world, but it is the largest commercial building in the world. You will find an entire 2-city block span of retail services within, from high-end home design and furniture to fashion apparel and accessories. Find health centers, banks, USPS offices, and even a Fed Ex inside, plus a full food court and selection of eateries. We highly suggest you head up to the 9th floor to the apparel level, housing such icons as 360 Cashmere, Argo Furs, Central Park West, and many, many more. After your visit, you will easily see why this spot is known for it’s ‘innovation and creativity for interior designers and business owners’.