Chicago also known as the second city or the 'windy city' is the third largest city in the U.S. but not necessarily the best place for watch shopping, if we really want to be quite blunt. Chicago offers a decent amount of specialized watch stores and only one dedicated watch boutique—Rolex boutique operated by Tourneau Watch Company. Watch stores are somewhat spread out around the city but with the main stores concentrated in two areas of the city, on the Magnificent Mile—Michigan Avenue— and Jeweler's Row along Wabash avenue in the heart of downtown.
As we start our watch shopping way around Chicago, we kick-off around Jeweler's Row. This row, located on Wabash avenue heading south between Washington and Monroe streets, offers a wide variety of pre-owned watch shops, a few gray dealers and just two authorized dealers—New York Jewelers and Marshall Pierce & Company. New York Jewelers carries a large selection of brands such as TAG Heuer, Bell & Ross, U-Boat, Chronoswiss and a nice selection of pre-owned vintage Rolex watches. Located about a block away from NYJ, right inside the building located at 5 South Wabash—Jewelers Center—, you'll find several watch dealers including the well known Howard Frum—one of the largest pre-owned watch dealers in the Midwest.
Heading north on Michigan avenue from Millennium Park right next to Allen Edmonds and a few steps away from the corner with Ohio, you will find the recently opened Tourbillon Boutique, specialized in very high end names such as Breguet, Blancpain, Glashütte Original, Omega and Jaquet Droz. A block and a half away—still heading north on Michigan avenue—and on the opposite side of the avenue at the corner of Ontario and Michigan, Cartier and the Rolex boutique are located.
Catty corner from the Rolex boutique and a building away from the corner with Erie, you'll find, Swiss Fine Timing Atelier Jewelers. This store is the only authorized dealer for Audemars Piguet and Richard Mille and also carries other great names such as Hublot, Breguet, Parmigiani, Panerai, Graham, Chopard, Zenith and Glashütte amongst others.
Three blocks north from here you can stop at the Ralph Lauren boutique and check out their vintage watch section on the lower lever. Two blocks north inside the Water Tower Place shopping mall is where Tourneau is located. Wide selection of Breitling, Patek Philippe, Rolex, IWC, Longines and Panerai. A block north next to the Westin on Michigan avenue you will stumble upon the Omega, Bulgari and Louis Vuitton boutiques, finding Montblanc just right across the street from them. One block north from Louis Vuitton, you will make a left on Oak street and about half a block away on the right side you'll find Geneva Seal, authorized dealer for Roger Dubuis, Breitling, Frank Muller, Blancpain, Urwerk, Jacob & Co., Bell & Ross and TAG Heuer amongst others. Last stop the Hermès boutique on Oak and Rush street. From there make sure you have lunch or dinner at Fred's inside Barney's New York.