Chicago Shopping and Sights
Collected by Nicole Schnitzler, AFAR Local Expert
One of Chicago’s 50+ million annual visitors? This list can help you tackle the world-class sights: shop vintage boutiques, conquer your fear of heights at the Willis Tower, stroll an extraordinary garden or museum. Trust us, you won’t be bored.
5216 N Clark St, Chicago, IL 60640, USA
Located just two blocks from Wrigley Field, this apparel fun house has been making a name for itself ever since 1983 for its quirky threads (not to mention a solid inventory of Converse Chuck Taylors and whoopee cushions). Once you’re here,...
1643 N Damen Ave, Chicago, IL 60647, USA
Tricia Tunstall opened the doors to this Bucktown boutique in 1997, making it a pioneer in the area for its upscale and diverse design lineup in women’s apparel. That roster features tops, dresses, bottoms, shoes, jumpsuits, and accessories...
851 W Randolph St, Chicago, IL 60607, USA
This skin-care sanctuary just opened its doors in Fulton Market’s bustling neighborhood after spending two years in Roscoe Village, where it built an obsessive following for its handmade products. The line was inspired by the...
1528 N Milwaukee Ave # 1, Chicago, IL 60622, USA
It’s always been about affordable vintage goods at this Wicker Park boutique, which sells contemporary dresses and tops from Amuse, men’s hats from Brixton, denim from skinny-jean pros Just USA, rompers from Los Angeles–based En...
118 N Clinton St #205, Chicago, IL 60661, USA
This haven for relaxation specializes in services both familiar and hard-to-find, including Ashiatsu massage (a back-walking technique that delivers even, deep pressure) and sugaring, a hair-removal process that is considered the gentlest by...
2327, 833 W Washington Blvd, Chicago, IL 60607, USA
Chances are you’ve seen Maria Pinto’s works at some point in recent years—she’s known for dressing the likes of First Lady Michelle Obama, Oprah Winfrey, and Brooke Shields. That fan base is only growing with the opening of...
2780 N Lincoln Ave, Chicago, IL 60614, USA
This Lincoln Park destination, besides being one of the only designer-toy shops in the Midwest, has gained a reputation for being one of the best designer-toy shops in the world. It stocks a wildly diverse selection of vinyl figures and...
2136 W Fulton St unit j, Chicago, IL 60612, USA
The inspiration for this Chicago-based apparel retailer came from the desire to make timeless, hardy menswear at the right price—and in the United States. As such, its pieces range from button-down sports shirts and heavy-duty-denim work...
1870 N Damen Ave, Chicago, IL 60647, USA
This Bucktown lifestyle boutique carries everything for the home, closet, and beyond—and at an affordable price point to boot. Owner Emily McKenney curates an inventory focused on Chicago designers (Le Coeur, Sophia Reyes, Ali's Collection,...
951 W Armitage Ave, Chicago, IL 60614, USA
After studying culinary arts at Le Cordon Bleu, Chicago resident Katrina Markoff took some time to travel—a journey that planted the seed for Vosges Haut-Chocolat, a line of premium chocolate made with globally sourced spices, flowers,...
1600 N Lake Shore Dr, Chicago, IL 60613, USA
Chicago has no shortage of beaches, but there are few that boast the views, convenient location, and activities of North Avenue Beach. Located just footsteps away from the Lincoln Park Zoo and the vibrant shopping and nightlife of Old Town, this...
1300 N Dearborn St, Chicago, IL 60610, USA
Restoration Hardware, the upscale home-goods store, made its 2015 Gold Coast debut in style, taking over a building that was created in 1914 as a residence for young women studying music, drama, and the visual arts. Architect James Gillam of...
1945 S Halsted St, Chicago, IL 60608, USA
Art enthusiasts eagerly await the second Friday of each month, when galleries and boutiques situated in the Chicago Arts District (otherwise known as Pilsen East) open up their doors for an evening of wine, conversation, shopping, and art...
300 N Central Park Ave, Chicago, IL 60624, USA
Opened in 1908, this urban sanctuary was designed by renowned landscape architect Jens Jensen. The grounds—combining the display houses and outdoor gardens—cover 14 acres and feature more than 5,000 rare and exotic...
1913 W Division St, Chicago, IL 60622, USA
Founded by a husband-and-wife team in 2002, this Wicker Park boutique specializes in goods crafted by independent creators, with both local and international viewpoints represented. The styles are attractive and accessible, with an...
357 W Erie St, Chicago, IL 60654, USA
Those looking for a skin-saving stopover during their shopping sprees can swing into this River North spot where a team of experts offers facials for the beauty-savvy and on-the-go. Guests select from a menu of several applications that address...
934 W Armitage Ave, Chicago, IL 60614, USA
This shop has been supplying Lincoln Park tastemakers with the finest jewelry, women’s clothing, home decor, stationery, and gifts since 1984—all at a range of price points and styles. Today, those items include the works of jewelry...
100 S Morgan St, Chicago, IL 60607, USA
Adventure awaits at this West Loop indoor playground, where visitors can boulder, auto-belay, and rappel their way through 25,000 square feet of space. Pros can take to the walls in no time, but those seeking a little more guidance (or off-wall...
1807 S Allport St, Chicago, IL 60608, USA
A visit to Pilsen isn’t complete without a stop at this historic concert hall, a must for national musical acts and local talent—not to mention the spectators that get to enjoy it all. It was John Dusek who originally opened doors here...
5535 S Ellis Ave, Chicago, IL 60637, USA
Situated in the city’s Hyde Park neighborhood, this theater opened in 1955 and has been appealing to crowds near and far ever since for its diverse programming and community involvement. Each season focuses on five productions—a range...
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
1400 S Lake Shore Dr, Chicago, IL 60605, USA
Dinosaurs, pyramids, cave paintings, sharks—if you don't like the Field Museum then you must never have been a kid. Home to an extensive assortment of magical displays highlighting all facets of natural history from around the world, the...
1300 S Lake Shore Dr, Chicago, IL 60605, USA
It’s difficult to design a museum suitable for both kids and adults, but Adler makes it look easy. Children will love the area known as Planet Explorers, where they can play astronaut with space rovers and rocket-launch simulators, peer...
2001 N Clark St, Chicago, IL 60614, USA
It's enormous, it's full of animals, it's open all year round, and, best of all, it's (gasp!) free. The Lincoln Park Zoo is one of the single greatest things to do in Chicago. Visit the monkeys in their house of hilarity, or swing past the penguin...
1513 W Foster Ave, Chicago, IL 60640, USA
Adam and Skye Rust admit that they have a thing for taxidermy. And bones. And teeth. Adam has even made an animated sculpture where taxidermied mice circle and dance à la "Three Blind Mice." They travel the globe to find the strangest and...
1432 W Chicago Ave, Chicago, IL 60642, USA
Teenage Mutant Ninja Turtles T-shirts, Members Only jackets, Beavis and Butthead outerwear, Max Headroom sunglasses… oh yes, these are all the droids we’re looking for. Visitors on the hunt for totally tubular leg warmers, an...
1472 N Milwaukee Ave, Chicago, IL 60622, USA
This charming little store on Milwaukee is stuffed with vintage goods in primo condition. Beautiful chunks of costume jewelry and frilly fascinators share space with lush leather handbags and sparkling glassware. Nothing in the store is cheaply...
3020 N Lincoln Ave, Chicago, IL 60657, USA
Like most good thrift stores, the Brown Elephant is hit or miss. Sometimes you can find great books, T-shirts, and super-cheap vinyl—other times, nothing appeals, and you just wander around until your feet hurt. This shop is well organized,...
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