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Chicago’s oldest and best-known department store is most famous for its elaborate Christmas displays, dazzling Tiffany dome, and iconic clock. Nearly 100 years after opening, this flagship store continues to offer top styles for home and body (see State Street).

You’ll find some fantastic budget-friendly buys as well as a dreamy shoe department in this ornate, historic, 12-story department store (see Carson Pirie Scott Building).

After 18 years away, a hipper Sears returned to State Street in 2000 offering five levels of everything from tools to toddler outfits.

This wonderful bookstore is the world’s largest that is dedicated to architecture and related fields. It’s a staple for architecture students, but also a fascinating browse for anyone.

On the strip commonly known as “Jeweler’s Row” this one-stop-shop is a friendly place to source gold, pearls, watches, diamonds, and gems at relatively low prices.

High style on sale at a fraction of the original prices lure bargain hunters to this charming little sister of the upscale and pricey Nordstrom.

This enormous store opposite The Art Institute of Chicago sells contemporary, vintage, and collectors’ posters, as well as artsy gifts.

Teenage artists involved in an arts training program create the incredible paintings, sculptures, and other artwork sold here. All proceeds from sales are returned to the program.

This regional flagship store offers the ultimate Old Navy shopping experience, with two floors of discount jeans and T-shirts, and other casual comfort clothes at bargain prices.

A smoker’s paradise since 1897, this store now sells around 100 cigar brands, 15,000 pipes, and countless smoking accessories. It also contains a small tobacco museum.