The Drake Hotel This old-school hotel has history on its side: It’s been a Chicago landmark since 1920 and marks the beginning of the Magnificent Mile. The gift shop celebrates the hotel via Drake souvenirs such as coffee mugs and T-shirts. The store even offers Drake Hotel chocolates to satisfy customers’ sweet cravings. 140 E Walton Pl (312-787-2200). Mon–Fri 7am–10pm; Sat, Sun 7am–9pm.
Hard Rock Hotel As you’d probably guess, it’s all about music-themed souvenirs at the Hard Rock. The gift shop sells drumsticks, guitar picks and collectible “rock-star” Barbies. You’ll also find a couple of mix-CDs with tracks recorded by musicians such as Bruce Springsteen, Avril Lavigne and John Lennon specifically for the albums. (Profits from album sales go to the Why Hunger foundation.) 230 N Michigan Ave (312-345-1000). Mon–Thu 8am–10pm; Fri, Sat 8am–11pm; Sun 8am–9pm.
Trump International Hotel & Tower Donald Trump isn’t one to go cheap, so it’s a no-brainer that his hotel gift shop carries far more than the average toothbrush and Advil. The small shopping area offers Olivia Riegel–designed studded and sparkling picture frames as well as jewelry and purses. Although it provides ritzy accessories, the boutique is also well-stocked with the everyday necessities. 401 N Wabash Ave (312-588-8000). Mon–Fri 8am–8pm; Sat 8am–10pm; Sun 9am–4pm.
The W Lakeshore This hotel offers great views of the city, and for more Windy City love, visit the gift shop for clothes, candles and jewelry inspired by Chicago. The pieces are part of the Global Glam Collection, which offers custom designs based on the cities surrounding the shops. While the Chicago hotel’s store focuses mainly on women’s apparel and accessories, with a few items for men and kids, a wider variety of options, including furniture, is offered online. Gift registry is also available on the website. 644 N Lake Shore Dr (312-943-9200). 9am–10pm daily.