Things to Do in Chicago

Jonny Valiant

Au courant blazers created by Marie Whitney—the wife of Chicago Cubs president Theo Epstein—are go-anywhere closet staples beloved for their tailored... Read More

What could be better than spending a Friday evening exploring the eclectic galleries of the Chicago Art District? How about socializing with the artists... Read More

With views of the city from the top of the John Hancock Center, the observatory is 1,000 feet up in the air and features Tilt, a viewing platform that... Read More

Ducking into this expansive basement shop feels like discovering a secret chamber of the Hogwarts vaeiety. Five rooms—complete with cozy reading nooks... Read More

Ducking into this indie, bibliophile paradise is like being transported to a secret chamber in a Medieval castle. New releases and classics are... Read More

The non-academic sister store to the Seminary Co-op, 57th Street Books is located underground in an unassuming red-brick building in Hyde Park. Inside,... Read More

Known for statements like “less is more” and “God is in the details,” the minimalist residential buildings at 860 and 880 LSD are exemplary industrial... Read More

The ultimate shopping experience, 900 North Michigan boasts six floors of more than 70 luxury retailers, comprised of both national brands and boutiques... Read More

This bright, exotic looking “stabile” stands in stark contrast to the Bauhaus style office buildings in its midst. And, that was the plan. Though it... Read More

Tucked behind modest gates is this secret garden, a Prairie-style masterpiece that was designed in 1939 for the people of  the “megalopolis” to... Read More

Located in a very popular shopping area along North Michigan Avenue, Alternatives not only stays ahead of current trends, but has been know to inspire... Read More

A space dedicated to more than 90 merchants and their wares, Andersonville Galleria is a truly distinct destination in the city. This neighborhood... Read More

Whether you are hoping to hit the “Big 3” (Rome, Florence and Venice) with tots in tow, sample phenomenal wines in the alluring region of... Read More

For more than 40 years, this upscale River North spot has been quenching Chicagoans’ thirst for jazz. And, they do so more than once a day. Its famous ... Read More

Known for soigne editorial work, ad campaigns, and a celebrity clientele, Anthony Cristiano is Chicago’s shear genius. His hair salon at the Trump Hotel... Read More

Style-savvy men frequent this Bucktown clothing boutique to find the latest fashions from both established and emerging designers. Owned by sisters Amy... Read More

If your vacation fantasy includes getting glammed-up without the stress of coordinating multiple appointments all over town, Lincoln Park’s beauty... Read More

Housed in the 1904 Santa Fe Building designed by Daniel Burnham, the Chicago Architecture Foundation’s ArchiCenter features temporary exhibits as... Read More

Checking out the city’s dreamy architecture (Tribune Tower, Wrigley Building, Civic Opera House) from a mobile perch in the Chicago River is a must-do.... Read More

The AIC is home to more than 300,000 artworks from the far reaches of the globe. Within the collection are works by noted artists such as Monet, O’Keefe... Read More

The airy, bright atmosphere of Greektown’s Atropolis is a welcome respite from the concrete of the city. Modeled after European cafés and... Read More

In operation since 1916, the Arts Club of Chicago hosts three public art exhibits each year in its gallery space on East Ontario Street. The building,... Read More

Known for voluminous cuts and dramatic necklines encrusted with Swarovski crystals, Azeeza Khan’s glitzy, Indian-inspired label is a favorite of Chicago... Read More

What started as a food truck has transformed into a brick and mortar magnet for lovers of fresh, Southern-style baked goods. Each day there is a... Read More

Like its NYC cousin, Barney’s Chicago is a bright, airy, and whimsical shopper’s paradise committed to showcasing all that is trending from the Americas... Read More

Almost nothing symbolizes a Chicago-experience more than a hot dog (with all the fixings) and an afternoon baseball game. In 2014, Wrigley Field... Read More

Even celebrities like Julia Roberts and Naomi Watts have relied on this boutique for stylish, non-frumpy maternity clothes. Located in Wicker Park, the... Read More

Whether you’re hoping to master complicated dance floor dips or simply tame your two left feet, Big City Swing has you covered with well... Read More

This high-concept Logan Square club pays close attention to each individual ingredient, from the exclusive bitters and colas to hand-hewn ice cubes.... Read More

Eleven months out of the year, this unassuming River North storefront goes unadorned, with no signage, no merchandise displays and a hard-to-find... Read More

For over thirty years, Dominic Marcheschi and Marilyn Blaszka have been fashion pioneers. Together, they’re bringing the crème of the runway crop to... Read More

This airy, bright salon is the spot for a simple, inexpensive, no-nonsense blowout. The process is simple. Bring in a picture of your desired tresses,... Read More

River North’s neighborhood blues bar, Blue Chicago is notorious for its songstresses. Grana Louise, Big Time Sarah, Laretha Weathersby, Dimetria... Read More

Quality over quantity is the rule of thumb at this small, independently owned bookstore in Lincoln Square. Behind a glass storefront brightened by... Read More

Tucked under the EL tracks on a street populated by fellow indie shops, this bookstore and adjoining café is a beacon to the Lincoln Square community.... Read More

It’s not the drinks that are the star at this rooftop. Nor is it the view (though the 29th-floor spot overlooks the Hancock Building and the Sears... Read More

A friendly neighborhood hangout, Café Marianao serves sandwiches and café con leche in a bustling, bilingual atmosphere. Even if your... Read More

Top tip: Don’t miss early morning prayers at the Thiksey monastery, near Leh, in northern India. “When the prayers end, the younger monks... Read More

The younger, trendier sister store to Crate & Barrel, CB2 was founded in Old Town in 2000 and is now an ever-growing American and Canadian chain.... Read More

Since 1971, the Chicago Architecture Foundation has been offering walking tours of the downtown Loop area. Since then, it’s also added myriad... Read More

Bold architecture is one of the defining features of the city of Chicago, and discovering these buildings by boat is incredible. Filled with narrative... Read More

Dedicated to the art of play, exhibits such as WaterWays (pulleys and pipes, toy boats) and the Artabound Studio (paint, clay, and draw with trained art... Read More

Located in the Loop, the Chicago Cultural Center is known for both its impressive architecture and its free programming, which includes more than 1,000... Read More

Be your own boat captain on the Chicago River. Boat rentals run for up to four hours and up to 12 people. Read More

Margaret Hicks, a former Second City performer, does her tours a little differently. Her comedy-laced sightseeing experiences are informative, quirky,... Read More

Founded on the principle of supporting local farmers and artisans, the Chicago French Market houses a collection of vendors selling anything from olive... Read More

Chicago Gallery News provides free tours of River North’s many galleries on Saturdays from 11 a.m. to 12:30 p.m. Meet the guide on the corner of... Read More

The Great Chicago Fire, street food, architecture, dance, Millennium Park, Greektown, baseball, Lincoln Zoo - whatever Chi-Town topic you’d love... Read More

From fashion to photography, this museum’s refined 600-object collection explores both Chicagoan and American history. Multiple exhibitions (don’t miss... Read More

Located at the south end of the Lincoln Park neighborhood, the Chicago History Museum features exhibitions about the city’s compelling past. A... Read More

Sailing on either Chicago River or Lake Michigan, the educational boat tours offered by Chicago Line Cruises are some of the city's most popular... Read More

In a neighborhood dotted with music venues, this instrument shop fits right in. Even if you’re not in the market for a vintage Fender, the sheer... Read More

Why It’s Cool: Beneath the Gothic Chicago Tribune Tower, Art Deco NBC Tower, and bling Trump Tower, a garden of hot-pink and purple flowers... Read More

Even if you’re not traveling by train, Chicago’s Union Station is a destination in and of itself. Originally designed by the celebrated... Read More

Whether you’re a connoisseur of vintages or a new apprentice in the field of oenology, you can easily expand your knowledge with the help of the... Read More

On Friday and Saturday nights, indulge in the decadent Chocolate Bar at The Lobby on the fifth floor of The Peninsula Chicago. Sip a chocolate martini... Read More

Ideal for foodies and chefs of all skill levels, the Chopping Block is both a retail store and the city’s largest recreational cooking school. At... Read More

The view of the Chicago River is the crown jewel in the signature Chuan Spa, known for its serenity. The décor and treatments are based on an East... Read More

Walking tours can be tiring, and bus tours can feel disconnected. The Segway experience combines the best of both worlds. This 2-3 hour guided tour... Read More

In a neighborhood full of high-end retail, this women’s clothing boutique sets itself apart with an inventory of relatively affordable styles from... Read More

Ideal for shoppers seeking reasonably priced wardrobe basics, this small clothing boutique sells what owner Sandy Horwitz calls "every day wear for the... Read More

A modern reflective sculpture often referred to by locals as "The Bean." The artist was inspired by liquid mercury. It's a favorite of tourists for mind... Read More

One of the largest outdoor sculptures in the world, Anish Kapoor’s giant stainless steel orb known as “the bean” glimmers majestically from its perch... Read More

Known as the second establishment in Chicago to score a post-Prohibition liquor license, this vintage boite is known for its generous martinis (four... Read More

Part video installation, part play area, Jaume Plensa’s black granite reflecting pool banked between two 50-foot towers is true interactive art. As... Read More

These totes, backpacks, messenger bags, and carry-alls are the epitome of modern utilitarian. The gender-neutral pieces are finessed from repurposed... Read More

The blue bikes you see clustered all over the city are the perfect sightseeing opportunity. Simply determine your destination and buy a 24-hour pass... Read More

Once a down-trodden, Prohibition-era tavern, this Wicker Park enclave has retained its grittiness and emerged as a vibrant nightlife institution. Music... Read More

Drift is all about statement making specs—sunglasses and prescription—with soul. The biodegradable Italian acetate frames and sustainable wood temples... Read More

Inspired by “Art Brut”, or, outsider art, Dubuffet’s love of contemporary graffiti and a unique street style is evident in this multi-dimensional fiber... Read More

Those on the hunt for soul classics—as well as classic and contemporary jazz, funk, and reggae beats—can easily kill a day digging in this... Read More

Ideal for partiers who enjoy the laid-back dive bar attitude but not the traditionally grungy digs, this Rush Street nightspot combines an easygoing... Read More

Located in the Loop beside the 1926 Cadillac Palace Theatre, Encore Liquid Lounge is a casual lunch club by day and a cocktail bar by night, offering... Read More

As the black and white sign above the glass storefront proclaims, Erickson's Delicatessen has "everything for the smorgasbord." Established in 1925 in... Read More

Exhale Chicago is known for their hardcore workout clasees. But to caterpillar-browed women across the city, the spa’s true claim to fame is browmaster... Read More

A three-day pass allows you to curate your sightseeing experience by hopping on and off a trolley as you wish. Visit Chicago’s most famous attractions... Read More

Amid countless coffee chains, Fabcakes is a welcome change for your caffeine fix. Red velvet-draped walls add to the cozy atmosphere of this café... Read More

Beloved for its plot—a high school senior skips school to spend a perfect spring day in downtown Chicago with his friends—this coming-of-age film by... Read More

An award-winning museum of natural history, The Field was first built for the 1893 World's Columbian Exposition in Chicago. One of the most popular... Read More

For orinthology enthusiasts or would-be archeologists, you’ll find your thrills at the massive Field Museum. Home to more than 20-million specimens, the... Read More

This Hyde Park home ushered in the Prairie School and changed the face of modern architecture. Uniquely American, the design by Frank Lloyd Wright... Read More

Located on the University of Chicago campus, this landmark is considered one of the most significant structures in American architecture. Designed in... Read More

Commonly referred to as "landscape art under glass," this beautiful conservatory occupies approximately two acres inside and often plays host to special... Read More

Stroll down the Magnificent Mile and stop at Garrett Popcorn. Although the company now has stores throughout Chicago and New York City, the first one... Read More

Exposed brick walls, reclaimed-wood tables, floor-to-ceiling windows, and a quirky collection of taxidermy are, in fact, pivotal design details at this... Read More

From a wood and amethyst ring to white gold and blue topaz earrings, Gem showcases one-of-a-kind handmade accessories. In 2004, Laura Kitsos opened this... Read More

If you pine to see the highlights of the Cannes Film Festival, or watch obscure, Oscar-nominated shorts, the Siskel Center will be your cinematic... Read More

Founded by two Polish brothers, Gene’s boasts 40 varieties of artisan smoked meats and naturally cased sausages, prepared in-house, as well as an... Read More

George Greene is the Savile Row meets Fred Segal of Chicago. Discerning clientele flock to this menswear mecca for custom-Kiton suiting, Luciano Barbera... Read More

Whether you’re hoping to indulge in a leisurely breakfast, in need of quick lunch, or simply looking for a few gourmet goodies, Goddess and... Read More

Several distinguished stages make up the Loop’s theater district. Goodman, Chicago’s oldest and largest nonprofit theater, has entertained... Read More

A satellite of the flagship London store, Graff specializes in fine diamonds sourced from mines around the globe. Established by award-winning jeweler... Read More

Commonly referred to as Chicago's Front Yard, this 319-acre park holds many of Chicago's main attractions and is frequently the venue for annual events... Read More

Often referred to as the city’s “front yard,” this massive green space separates Chicago’s downtown from Lake Michigan. Grant Park is home to baseball... Read More

After arriving in the 1840's, many of Chicago’s first Greek immigrants resided in a section of town just west of the Loop. With the development of... Read More

Every Saturday, locavore-loving foodies and A-list chefs like Stephanie Izard descend on Green City Market—coffee in hand—to snap up the freshest... Read More

This delightful nonprofit boutique sells fair-trade and eco-friendly clothing, jewelry, housewares, and foodstuffs from artisans in more than 60... Read More

Rising 113 feet above the shore of Lake Michigan, the Grosse Point Lighthouse provides panoramic views of the water, as well as Chicago skyscrapers... Read More

Located in Wicker Park, this high-end boutique sells styles from both established and up-and-coming labels, including local talent like handbag designer... Read More

Bucktown’s fashion pioneer, Helen Yi, has been quietly outfitting Chicago urbanistas for over a decade. Her minimalist aesthetic is the perfect backdrop... Read More

Now a world-renowned brand lauded for its high-quality leather goods, Henry Beguelin originally began as a group of friends designing belts from leather... Read More

Ideal for those who spend more time in the air than on the ground, the Hilton Chicago O’Hare Athletic Club is actually located inside O’Hare... Read More

The Chicago area has plenty of couture ice cream operations—like Ruth and Phils Gourmet Ice Cream, with such arcane flavors as sour cream cinnamon... Read More

Experience downtown at your own pace with Chicago’s Hop On Hop Off Tours. Tours leave from 14 downtown locations every 20-30 minutes. Visitors can... Read More

Once a historic movie theater, the two-story venue transformed itself in 1996 as an outlet for up-and-coming jazz, R&B, funk, and hip-hop musicians.... Read More

Located on East Huron Street in a bright red building, this upscale women’s boutique is owned by Ikram Goldman, who at one time acted as Michelle... Read More

Ikram Goldman, Michelle Obama’s former stylist and major duomo of the enormous, red lacquer sartorial sanctuary bearing her name, can only be described... Read More

Located inside the Peggy Notebaert Nature Museum, visitors to this 2,700-square-foot greenhouse share the space with 75 bird species and one-thousand... Read More

Situated in Wrigleyville, this European-style coffeehouse is one of three Julius Meinl locations outside of Vienna, Austria (the other two are in... Read More

The mantra at this Chicago institution is indicative of the club’s riotous energy: “hear the blues, drink booze and talk loud.”  Founded in 1968,... Read More

The mantra at this Chicago institution is indicative of the club’s riotous energy: “hear the blues, drink booze and talk loud.”  Founded in 1968,... Read More

The first upscale women's clothing store in Lakeview, Krista K was established in 2002 and quickly became a go-to shop for fashion-forward Chicagoans.... Read More

Walk East and you will have a delightful rendevous with Lake Michigan. The 18-mile Lakefront Trail accomodates both pedestrians and cyclists, and... Read More

Located in Wicker Park, this Mexican bar and café is known for its well-balanced margaritas and its guacamole, which is prepared tableside and... Read More

With overstuffed royal-purple chairs, a French oil painting, and architectural books scattered throughout, Sofitel’s Le Bar feels like a nobleman... Read More

An hour with Leah Chavie feels like having a cameo on Star Wars. Her laser and her lights, however, take one to a much happier place—the planet of... Read More

Housed in a former gear factory, the Lillstreet Art Center, founded in 1975, accommodates students, teachers, and lovers of art in this spacious brick... Read More

Chicago’s largest park is home to the Lincoln Park Zoo and its siblings: the nature boardwalk and the Farm-in-the-Zoo. With 1,208 acres of rolling green... Read More

Even in the dead of winter, you can find a bit of paradise at the Lincoln Park Conservatory. Built in 1890 as a “paradise under glass,” this Victorian... Read More

Family-friendly (and free), the Lincoln Park Zoo is open to the public 365 days a year. With a wide range of wildlife and an adopt-a-pet program, this... Read More

Polar bears? Zebras? Rare red kangaroo?  With more than 1,200 animals, Lincoln Park’s zoo ranks as one of the finest in the country. Highlights... Read More

With more than 1,250 animals, Lincoln Park Zoo ranks as one of the finest in the country. Don’t miss the Endangered Species Carousel or Regenstein... Read More

To experience the true definition of “urban oasis,” stroll in and around this 14-acre ecosystem with the backdrop of the Chicago skyline. Connected to... Read More

Logan Square’s residents cheered the reopening of this 1915-built movie house, which has been refurbished in all of its Art Deco glory. Film... Read More

Bowling and martinis, anyone? Lucky Strike is a bowling alley that doubles as swank cocktail lounge. The 18 lanes, lacquered and illuminated by hallogen... Read More

The world’s largest collection of boutiques geared toward home furnishing and renovation, LuxeHome is a 100,000-square-foot space lined more than... Read More

There is an incomparable thrill divined from scoring designer duds at a fraction of their retail cost—especially without a lingering scent of camphor.... Read More

Identified as a National Historic Landmark, Macy’s on State occupies the extraordinary Marshal Field & Company Building. Shopping is a grand... Read More

Tucked away on the lower floor of 900 North Michigan Avenue, the cornflower-blue Mario Tricoci Spa team is quietly eradicating stress and defying the... Read More

Specializing in outsider and contemporary pop art, Mars Gallery is said to possess a special energy due to its location atop a purported vortex within... Read More

Opened in 2008 by comfort food chef Cynthia Kallile, this unusual Lakeview bakery delights diners with an assortment of savory cupcakes made with... Read More

Started in the 1930’s and now the city’s oldest continually operating tour boat company, Mercury is all about fun, laid-back sightseeing. No... Read More

Established by pharmacist Peter Merz in 1875, this old-fashioned apothecary has been serving Chicago natives for more than a century. The flagship... Read More

Founded in 2003 by the father and son duo of Jeff and Tony Dreyfuss, Metropolis is a small-batch artisan coffee roaster operating out of a 1950's... Read More

What do you get when you mix an uber-connected DJ, a seasoned visual artist, and a retail dynamo and plop them down on the best corner in Logan Square?... Read More

This neighborhood favorite offers a selection of delicacies. Choose from a variety of savory pies from the deli: lamp and potato; spinach and feta;... Read More

Millenium Park is a multifunctional green space peppered with impressive works of art, architecture, and gardens. Wade into the reflecting pool of the... Read More

In the heart of the Loop, this park is a multi-functional green space peppered with contemporary art and classic Chicagoan architecture. Wade in the... Read More

Millennium Park is a local gathering spot for both Chicagoans and visitors alike. The park holds several famous art installations, including Cloud Gate,... Read More

Since opening in 2004, the 24.5-acre Millennium Park has become a Chicago staple that lures renowned artists, architects, and musicians. Highlights... Read More

Trained architect Annie Mohop designs eco-friendly footwear that can be worn hundreds of ways by maneuvering the interchangeable ties. Her casual... Read More

Shopping on Halsted is plentiful, but MOI Boutique stands out. Occupying a cozy space on the trendy street, the shop features feminine clothes at... Read More

Credited with giving Frida Kahlo, Jeff Koons, and Gerhard Richter their first exhibitions, the MCA has been celebrating the creative process since 1967.... Read More

Add some color to an afternoon in Chicago with a visit to the Museum of Contemporary Art, one of the largest contemporary art museums in the country.... Read More

Spread across roughly 14 acres, Chicago's Museum of Science & Industry is one of the world’s largest museums, with more than 35,000 artifacts... Read More

One of the largest science museums in the world, the museum has more than 35,000 artifacts and special hands-on areas just for kids in addition to... Read More

In Lakeview off Southport Avenue, bright red lights illuminate the sign above an old-fashioned marquee at this retro theater. Completed in 1929 when... Read More

One of Chicago’s oldest used bookstores and a Wicker Park institution, Myopic Books offers bibliophiles more than 80,000 editions, including some... Read More

It’s only fitting that Chicago—home to the second-largest Mexican population in the United States—would have a world-class museum... Read More

Visit this urban ecosystem at Lincoln Park Zoo, where birds, fish, frogs, turtles, and insects frolic among native plants. Visitors enjoy free admission... Read More

Vintage furniture, local art, grilled sandwiches, and locally roasted Metropolis coffee beans are the stars of this hipster hangout, which dominates the... Read More

A distinguished independent research institution with over 1.5 million books, the stately Newberry Library holds free exhibitions and lectures, all open... Read More

Billed as Chicago’s oldest used bookstore, O’Gara & Wilson has been a preferred spot for South Side booklovers since it first opened... Read More

Always wished you could play the washboard? The Old Town School can help. They also offer lessons in playing the guitar, saxophone, or djembe drums, as... Read More

We could describe Open Books as a used bookshop, but it’s so much more than that. This nonprofit uses proceeds from donated books and its retail store... Read More

Established by two architects in 2001, Orange Skin is dedicated to providing American customers with access to modern international design. As such, the... Read More

Part of the University of Chicago, the Oriental Institute is both a research organization and a museum dedicated to the ancient Near East. Founded in... Read More

This garden oasis, once the site of the Japanese Pavillion during the 1893 World’s Columbia Exposition, is now a prized urban retreat. Reach this hard... Read More

Frederick Law Olmsted created this zen refuge for the 1893 Worlds Fair as a backdrop for the Japanese Pavillion. From a sandbar, an island was crafted... Read More

Flanked by bronze statues representing the characters in L. Frank Baum’s famous novel The Wizard of Oz, this quintessential city park has it all: tennis... Read More

One of the first fashion boutiques in Bucktown, p.45 was founded by Tricia Tunstall and Jessica Darrow in 1997. Since the day it opened, the shop has... Read More

Proprietor Karl Sorensen travels to Europe and South America three times a year to bring back rare finds for his home and tableware shop. Whether it... Read More

Inspired by her time spent living in Beijing, design enthusiast Betsy Nathan opened Pagoda Red in 1997 to sell 19th-century Chinese furniture and... Read More

Specializing in artisanal cheese, bread, and wine, Pastoral is a neighborhood favorite. Its sandwiches, made with crusty bread from beloved Bennison... Read More

For science buffs, this Lincoln Park museum is a treasure. You can amble through ecosystems, take an outdoor birdwalk with binoculars and get wet while... Read More

For science buffs, this Lincoln Park museum is paradise. Amble through ecosystems, bird watch with binoculars, and get wet while learning about river... Read More

The 60s were all about change. So, Mayor Richard J. Daley decided to try something new. He commissioned Pablo Picasso to create a massive 3D sculpture... Read More

With it’s prime location adjacent to historic Robie House, this unassuming but decidedly au courant café is the ideal spot for lunch or mid-day craft... Read More

Established in 1971, this independent shop specializes in high-quality used, rare, and discounted books. Near the University of Chicago, the store&rsquo... Read More

An alternative baby and children's boutique, Psycho Baby sells unique clothing, toys, and books for kids ages newborn to six. The 2,000-square-foot... Read More

One of three venues comprising the lakefront Museum Campus, the Adler was established in 1930, making it the first planetarium in the nation. Today, the... Read More

Browsing flea markets for vintage treasures is a decidedly non-tourist activity. This celebrated European-style antique market features 250 vendors... Read More

This Bucktown wine shop was founded by passionate co-owners Sean Krainik and Nathan Adams in 1998. Crafted from reclaimed, 100-year-old barn wood,... Read More

Though much of this classic 80’s film—which launched a young Tom Cruise into superstardom—takes place in Chicago’s suburban North Shore neighborhood,... Read More

Take a tour of the Hyde Park-home that revolutionized American architecture. Where once there were only formal, European-inspired living spaces (small,... Read More

From her own clothing line to the commissioned skirt-form sculpture hanging from the ceiling, owner Robin Richman displays her touch everywhere in her... Read More

For decades American Express Travel Insider Robin Turner has been a foremost expert on Hawaii, and while her personal interests include gardening and... Read More

This “spa for the spirit” focuses on near-mystical experiences that combine holistic add-ons with traditional therapies. Massages kick off with a chakra... Read More

Housed in a turn-of-the-century Schlitz Brewery tap house, this small Lakeview venue offers a mixed bag of bands seven nights a week. Featuring anything... Read More

A Lakeview institution, Schubas Tavern has featured nightly live music for more than 20 years. The building itself, constructed by the Schlitz Brewery... Read More

Named for renegade boozers during the Prohibition, this boite is a modern-day gin joint with a “spirit forward” point of view and inviting, modern-day... Read More

Named for renegade boozers during Prohibition, this bar is a modern-day gin joint with a “spirit-forward” point of view and timeless décor. Cocktails... Read More

Filled with unique home furnishings, the ever-changing storefront window of Scout never fails to draw passersby in from Clark Street. Owned by design... Read More

Before Tina Fey, Steve Carrell, John Candy, and Mike Myers were household names, they were all getting their start at the comedic incubator, Second City... Read More

Established in 1961 by a group of 17 bibliophiles, this community-owned shop is now considered one of the world’s finest academic bookstores and... Read More

This Lakeview shop is ideal for women who want the unique selection of a boutique but with more affordable price tags. Located beneath an appropriately... Read More

While wandering down Milwaukee Avenue, be sure to stop at the indie-minded startup Shop 1021, which sells a selection of well-edited gifts such as Fred... Read More

Centrally located in the Loop’s law office district, this casual bar is a popular choice for lunch breaks and after-work drinks. Created by... Read More

For the best views in town you're going to have to go up. Way up, 103 stories high that is, to the top of Chicago's Willis (Sears) Tower. At 1,353 feet... Read More

The country’s first museum dedicated solely to stained-glass windows, the Smith Museum is located inside Festival Hall on Navy Pier. The museum... Read More

This spotless Gold Coast spa takes a decidely European approach to nail care. Translation? Eagle-eye attention to detail and endless pampering.... Read More

Selling unique designer wares and making gardening popular and possible in the Windy City, Sprout Home doubles as a home décor store and urban... Read More

Started in the mid-seventies in a church basement by Jeff Perry, Terry Kinney, and Gary Sinise, the famed Steppenwolf Theater Company now has 43... Read More

If you love thought-provoking, sometimes disturbing drama, book tickets for an evening production at Steppenwolf. With eleven Tony Awards for... Read More

Men’s and women’s accessories and bags, furniture, and ceramics sit side-by-side in this design-driven boutique. Inspired by Colette in... Read More

This self-proclaimed “liquor spa,” located in the Near North Side, combines the styling of a lounge with the “treatments” of a... Read More

Louis Sullivan is often deemed the most important pioneer in American commercial architecture, and this historic city center is one of his capstones.... Read More

An homage to Swedish-American history and culture, this three-story museum is located in Andersonville, one of the country's most concentrated areas of... Read More

Home baker turned professional pastry chef Cindy Levine opened this Lincoln Park sweet shop in 2002. Located on Webster Avenue, the bakery's exterior is... Read More

With its white deli cases, waxed butcher paper, and gingham-patterned walls, you might be tempted to order a corned beef on rye or pastrami, but the... Read More

This quirky, custom T-shirt boutique is designed after an old school deli. Pick the style shirt you want, select your iron-on decal from dozens of... Read More

Floor-to-ceiling windows create a bright, open atmosphere at this Wicker Park clothing boutique. Inside, patrons find an ever-changing selection of... Read More

Bring your own bottle of wine and an appetite for gourmet Italian, and Terragusto will take it from there, creating a dining experience that is... Read More

A park and trail system along an abandoned rail line, this trail is especially good for biking, walking and running. The many art installations along... Read More

The city's premier art museum, the permanent collection is home to over 300,000 pieces scattered throughout eight buildings. Two iconic lion... Read More

Just like his Michelin-starred restaurant, Alinea, Chef Grant Achatz ‘s upscale cocktail emporium is about combining flavor, presentation, and service... Read More

This is one of only seven Bahai temples on earth and just one in the Western Hemisphere, built for the more than five million people worldwide who... Read More

This elegant cocktail lounge, located on the ground floor of Chicago's Peninsula hotel, is a popular after-work hangout for locals and travelers in-the... Read More

This cult-classic tale of comedic redemption definitely shows the grittier side of the Windy City. There are iconic shots of the neo-Nazi parade at... Read More

When Suzanne Collins blew into town to promote Mockingjay, she headed north of the city to famed indie book shop, The Book Stall. Ditto for Caroline... Read More

Chicago pulled double-duty as sinister Gotham City in Christopher Nolan’s incarnation of the blockbuster Batman franchise. Dozens of iconic buildings... Read More

Cocktail culture meets small plates at The Drawing Room at Le Passage in the Gold Coast neighborhood. This culinary cocktail lounge’s natural... Read More

While most museums have a firm “do not touch” policy, the Field is hands-on and kid-friendly. Originally founded in 1893 to house the... Read More

This most excellent catch-me-if-you-can action flick has a falsely accused Harrison Ford racing all over the city to avoid US Marshalls and bring the... Read More

Said to be the country’s oldest jazz club, The Green Mill has been a Chicago landmark for more than a century. Beneath its sparkling green neon... Read More

It's a hike. But, Green Mill's status as one of the oldest jazz clubs in the country (it opened in 1907)— including well-documented visits from Charlie... Read More

It's a hike, but Green Mill's status as one of the oldest jazz clubs in the country (opened in 1907), with well-documented visits from Charlie Chaplin... Read More

At 100 stories and more than 1,000 feet high, the John Hancock Building is the 12th-tallest building in the world (for now, anyway). Stacked X’s... Read More

Chicago’s answer to New York’s Fifth Avenue and Beverly Hills’s Rodeo Drive, the Magnificent Mile is the city’s shopping... Read More

Three feet wide at its narrowest, The Matchbox claims to be “Chicago’s most intimate bar,” and it may also be its tiniest. For its... Read More

The Motel Bar gives patrons the comforts and cocktails of a hotel lobby bar minus the hotel. Amidst red and black leather furniture and cylindrical... Read More

You can’t miss the palatial, 14-acre museum overlooking the serene Columbian basin. Home to attractions such as original costumes from Pirates of the... Read More

Its status as the largest science center in the Western hemisphere is impressive. But when you consider that the structure housing 35,000 artifacts is... Read More

Stroll around this 14-acre ecosystem, with the the Chicago skyline as its backdrop, and you’ll experience the true definition of “urban oasis.”... Read More

The Organic Gardener, based out of Glencoe, IL, works with a range of gardening skill levels, from aspiring, novice gardeners to more experienced green... Read More

From the second you arrive in the lobby of The Peninsula Spa, you’ll be transported. Natural wood interiors and raku-style tiles evoke an Asian oasis,... Read More

The Water Tower and Pumping Station were the only public buildings left standing after Miss O’Leary’s cow allegedly knocked over a lantern... Read More

Tucked deep in the financial district is a stunning example of one of America’s first commercial skyscrapers. Here, architects Daniel Burnham and John... Read More

Founded in 1959 by Alan Arkin and several cohorts, this comedic theater company has been the training ground for the likes of John Belushi, Mike Myers,... Read More

Instead of visiting the John Hancock Center’s zenith during daylight hours, opt for an evening cocktail in the building’s high-flying lounge... Read More

Since the late 1920’s, the Swedish Bakery has been serving European-style pastries, cakes, and breads inside a standalone red-brick building in... Read More

Enjoy great wines and knowledgeable, friendly service in this former warehouse/current wine bar. The warmly lit, romantic ambience, stunning views of... Read More

The Water Tower and Pumping Station were the only public buildings left standing after Miss O’Leary’s cow allegedly knocked over a lantern... Read More

Special Booking: Jensen creates itineraries such as tours of Greenland’s northernmost reaches above the Arctic Circle by private helicopter and... Read More

Established in 2003, this tiny Lincoln Square shop offers a unique selection of high-end shoes displayed in a bright interior with hardwood floors,... Read More

Owned by a mother and daughter team, Tula sells a well-edited collection of European and contemporary designs in a charming vintage brownstone. Find the... Read More

Bold, silk-screened tunics and African-inspired jackets stand out against the white-washed interior of Tusk. This hybrid fashion boutique does double... Read More

It’s the unisex bathroom at Vertigo that first caught our attention. With a large round window overlooking the Chicago skyline and another window... Read More

Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grassroot... Read More

Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grassroot... Read More

Pull back the plush cobalt-blue drapes and reveal parquet wood floors and whimsical leather chairs with exagerated high backs that, when grouped... Read More

The stone Greek god and goddess banking the spa’s changing rooms are symbolic of the sybaritic pampering (try the new silk peel facial) that awaits... Read More

On a clear, warm day, admire Chicago’s architecture from a unique vantage point: the Chicago River. Wateriders offers guided kayak tours through... Read More

Wave patrons can take in Lake Michigan views while sipping cocktails at this lounge located in the W Chicago – Lakeshore hotel. Overlooking... Read More

A stellar bourbon list and a thoughtful craft beer selection make this vintage tin-ceilinged tavern worth the trip off the beaten path. Dim lighting and... Read More

Inside this Andersonville shop, designed with whitewashed floors and coffered ceilings, owner Terry Ledford showcases hand-selected, refinished vintage... Read More

Think of it as the world’s tallest recycling effort. Or maybe it’s just an exceptionally ambitious retrofit. In any case, the record... Read More

All children wish they could fly like Peter Pan. At the Willis Tower Skydeck, this dream can be realized. Step out on the ledge, a staggering 103 floors... Read More

Founded by two Chicago women designers, Wolfbait & B-girls sells the wares of more than 170 local artisans. The shop’s name harks back to a... Read More

Founded in Andersonville in 1979, Women & Children First is one of the largest feminist bookstores in the country. Behind a glass storefront with a... Read More

As the name implies, this Andersonville storefront caters to women. In fact, it is one of the largest feminist bookstores in the country, stocking... Read More

The grand-daddy of modern architecture, Frank Lloyd Wright is a Chicago icon. This all-day guided bus tour includes visits to celebrated buildings like... Read More

Often referred to as “Chicago’s Big Ben,” this gleaming white terra cotta “wedding cake” became the city’s first landmark skyscraper north of the... Read More

Ferris Bueller had the right idea: There is no better way to spend a sunny Chicago afternoon than at a Cubs baseball game. Wrigley Field is an icon for... Read More

Wrigleyville is the primary destination for many travelers to Chicago. Cubs fans flock to Wrigley Field on game day despite their beloved team’s... Read More

Tucked into the shadows of stately Gold Coast brownstones, thing tiny-yet-tony piano bar is filled with kitschty-cool zebra memorabilia. Opened the day... Read More

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