Chicago Shopping and Sights

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.

Highlights
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 cofounders’ mission to create items free of parabens, sulfates, and dyes, and to date they’ve already whipped up soaps, scrubs, masks, and body butters. If that wasn’t enough to keep them busy, the shop also runs several wellness classes a week (including yoga and meditation), along with a six-seat mask bar, where guests can customize their own clay masks with the guidance of skin-care pros.
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 Crème, and handcrafted leather boots from Red Wing. The popular shop’s homewares and apothecary section is arguably the best place to pick up gifts your friends will love, from grooming and shaving goods to candles, perfumes, and barware like flasks and cocktail shakers.
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 her West Loop Style Studio, where women can shop M2057 by Maria Pinto, a ready-to-wear collection inspired by urban architecture and design. Created for the time-pressed but fashion-forward woman, Pinto’s pieces marry runway ideas with a low-maintenance aesthetic (the upscale fabrics might be imported from Italy, but they’re also machine-washable and wrinkle-resistant—perfect for travel). In addition to plenty of day-to-night options like dresses, skirts, tops, and pants, the boutique also carries belts and jewelry by outside artists, curated by Pinto.
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 pop-culture collectibles from creative brands across the globe, including Kidrobot, Funko, Tokidoki, and Amuse. Still, it’s their “blind box” toys that sell fastest—customers don’t know which toy in a collection or series they’re buying until they open the box post-purchase. The shop’s other areas come with surprises, too: An adjacent gallery houses artwork, and its 1,000-square-foot space is available for private events (when it’s not hosting monthly BYOB Drink n’ Draw parties).
1600 North Lake Shore Drive
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 destination features a $7-million beach house, an abundance of volleyball courts, and the always-packed Castaways Bar & Grill, where locals and visitors enjoy daiquiris, tacos, and the latest Top 40 tracks. Throw down a towel and reap the benefits of Chicago’s warmer months, or try your hand at any of the on-site activities, including yoga and stand-up paddleboarding.
1300 North Dearborn Street
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 Backen, Gillam & Kroeger oversaw the redesign of the 70,000-square-foot structure, creating a six-floor showcase for luxury furnishings. It’s also the first Restoration Hardware to include a culinary element: The ground level features the Three Arts Club Café, where guests can enjoy breakfast, lunch, and dinner while surrounded by heritage olive trees and a refurbished historic fountain.
2007 W Churchill St, Chicago, IL 60647, USA
Rising nearly 18 feet above street level, the 606 (which takes its name from the common numerals in all Chicago zip codes) serves as a 2.7-mile elevated park and trailway for cyclists and runners, while also connecting neighborhoods through the reuse of an old industrial rail line and repurposed bridges. Visitors can access the attraction via 12 points (there’s one approximately every quarter mile), and once you’re on, a collection of temporary and permanent art exhibits, lush greenery, and city sights will make it difficult to exit. When you are finally ready to break away, you’re bound to end up somewhere good—access points serve the neighborhoods of Wicker Park, Bucktown, Logan Square, and Humboldt Park, meaning a post-walk bite and beer at one of the city’s best is just seconds away.
112 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady Cruises, which calls upon expert docents provided by the Chicago Architecture Foundation to reveal extensive history, culture, and style insights (for example, how the design of Willis Tower was based on cigarettes, or how the Monadnock Building on Jackson Boulevard was fabricated with 100 different shapes of brick). Book anytime between May and November for these rides, which run every day of the week and last 90 minutes.
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 various needs by way of thoughtfully selected ingredients, from sandalwood and kale to lemon and charcoal. There’s also the breast-milk facial—a treatment incorporating its namesake ingredient (plus vitamin E and clay) that brightens skin and combats acne. Everything on the menu follows a five-step process and lasts 30 minutes, meaning you can be in, out, and radiant in no time.
1807 South Allport Street
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 in 1892 with the hopes of bringing arts and entertainment to the neighborhood’s Bohemian community, and that same look and feel (the building was allegedly modeled after the Prague State Opera House) remained virtually untouched until 2013, when hospitality group 16” on Center took over. In addition to restoring the grand old building to its former glory, the team brought with them a few other bonuses, including the Michelin-starred Dusek’s Board & Beer, the cocktail bar Punch House (which, true to its name, serves some offerings by the punchbowl), and the modern-day piano bar Tack Room.
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 plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.
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 tube” design by architectural firm Skidmore, Owings & Merrill was originally inspired by a handful of cigarettes and the innovative bundling changed the construction of supertall, wind-resistant buildings thereafter. The tower’s height is even more thrilling when measured from the 103rd-floor windows of the Skydeck observatory and the Ledge, a glass-enclosed box which juts more than four feet out from the side of the building so that visitors can (gingerly) walk out and stand 1,353 feet above the street.
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 Field Museum is a great way to spend a day getting your culture fix. If you start to lose steam, just pop into the café for a meal to reenergize before continuing to explore the multitude of exhibits that await you. And while the museum is a showcase for natural history, it’s been at this spot since 1893, which makes it a part of history as well.
1300 S Lake Shore Dr
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 through microscopes, and crawl through caves and tunnels. Adults will love the Our Solar System exhibit and the CyberSpace room. The Adler is housed in a large semicircular stone building right on the banks of Lake Michigan, with giant glass windows on both floors and lovely views across the lake. It has an enormous telescope and a couple of star theaters with daily shows spotlighting space travel, night-sky vistas, and interplanetary relationships. Whether you go by yourself or bring your kids, it’s a great place for visitors of any age.
1840 W Hubbard St, Chicago, IL 60622, USA
You know that saying “They don’t build them like they used to”? Well, anyone who’s ever bought a new home knows exactly what that means. Fortunately, Salvage One’s mission is to preserve, conserve, and recycle glorious architectural remnants from old homes and buildings before they get hauled to the wrecking yard. With 60,000 square feet of space in the Near West Side neighborhood, Salvage One is packed with items like stained glass, claw-foot tubs, and big wooden doors; small, intricate accessories like doorknobs and drawer pulls; and vintage furniture and lighting. The store makes furniture, rents pieces as props for films and theater, and hosts private and corporate events. It’s an eclectic mix of services—but that’s Salvage One for you.
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 most visually impactful specimens to fill the motionless zoo and touch-friendly museum that is Woolly Mammoth Antiques & Oddities. Brussel Sprouts, the real two-headed calf (from Brussels); a ceremonial Odd Fellows skeleton; vintage medical tools; and old apothecary bottles all share space in this retail wonderarium. Not everything in Woolly Mammoth is a curiosity, but if it’s the unusual you’re seeking to buy, you’re bound to find it here.
1511 West Berwyn Avenue
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 acid-washed jean jacket, and a Michael Jordan bobblehead need look no further than Rad Vintage, supplying all the vintage toys, clothing, videos, and accessories that our inner kids could ever dream about. It’s one of the biggest vintage stores in Andersonville; the merchandise is in spectacular condition, and the prices are reasonable. It’s rad, man.
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 made—or priced—but all of the items are carefully selected for maximum appeal and quality. Shoppers who come in to browse will likely find treasures they simply can’t live without, because Store B Vintage has some of the prettiest retro pieces in the city.
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, and most of the home goods are reasonably priced. All of the proceeds go to benefit the Howard Brown Health Center, a great LGBT charity; if you’re waffling on spending a couple extra bucks, just go for it and know that your money is going to help someone who needs it. (The Brown Elephant has three outlets: this one in Lakeview, one in Andersonville, and one in Oak Park.)
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