Windy City Wanderings: A Local’s Guide to the Best of Chicago
Windy City Wanderings: A Local's Guide to the Best of Chicago - The Architectural Marvels of the Windy City
Chicago is renowned for its architectural wonders that reflect the city's history and diversity. As you explore the streets of Chicago, you'll be amazed by the variety of building styles and the stories behind them.
One of the most iconic structures is the Chicago Water Tower, one of the few buildings that survived the Great Chicago Fire of 1871. This 154-foot limestone tower looks like a miniature castle, complete with turrets and crenellations. It originally housed a large water tank that supplied water to the city. Today it still stands as a proud symbol of Chicago's resilience.
Just north of the Water Tower lies the Magnificent Mile, home to glitzy high-rises and luxurious shopping. The John Hancock Center, with its distinctive crisscross trusses, is one of the most recognizable skyscrapers. For sweeping views, hop on the elevator to the 94th-floor observatory. Nearby, the Tribune Tower incorporates fragments of famous buildings like the Taj Mahal into its Gothic Revival design.
Venturing into the Loop, you'll come across late 19th-century architectural gems. The Chicago Board of Trade Building epitomizes the Chicago School style with its glass and steel facade. Across the street, gaze up at the 330-foot tall Chicago City Hall with its grand, neoclassical columns.
As you stroll Grant Park, admire the Beaux-Arts beauty of the Art Institute of Chicago. Its exterior features immense bronze lions guarding its doors. Then cross the street to witness the majesty of Millennium Park's postmodern Jay Pritzker Pavilion, designed by Frank Gehry. Its billowing steel ribbons form a unique trellis for the outdoor concert venue.
No tour of Chicago architecture is complete without viewing some of Frank Lloyd Wright's Prairie School designs. Robie House in Hyde Park showcases Wright's innovative linear geometry with its horizontal lines and overhanging roofs. Rookery Building downtown also exhibits his signature style in its soaring light-filled atrium.
Chicago's neighborhoods also boast architectural diversity. Take a trip to Pilsen to see bright Mexican-style murals, South Side to find stately Greystone homes, and Old Town for its rows of charming Victorian houses.
What else is in this post?
- Windy City Wanderings: A Local's Guide to the Best of Chicago - The Architectural Marvels of the Windy City
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Hitting the Lakefront Path for Stunning Skyline Views
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Indulging in Chicago's Famous Deep Dish Pizza
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Exploring The Art Institute's Impressive Collection
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Taking in a Show at Historic Theaters Along State Street
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Wrigley Field: America's Most Iconic Ballpark
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Visiting The Local Favorites in Vibrant Wicker Park
- Windy City Wanderings: A Local's Guide to the Best of Chicago - Discovering Chicago's Diverse Neighborhoods on Foot
Windy City Wanderings: A Local's Guide to the Best of Chicago - Hitting the Lakefront Path for Stunning Skyline Views
Chicago's spectacular skyline comes alive along the Lakefront Path, an 18-mile trail hugging the shores of Lake Michigan. This ribbon of concrete meandering by beaches, marinas, parks, and skyscrapers makes for an exhilarating urban hike or bike ride. Gliding along the path feels like traversing through the heart of the city, with ever-changing vistas of architectural icons.
The views along the northern portion display Chicago's famed high-rises in all their glory. As you pass Ohio Street Beach, you can marvel at how the corncob shape of Marina City's dual towers contrasts with the stepped ziggurats of Lake Point Tower. Further south near Oak Street Beach, you'll gaze up at the Stonehenge-like monoliths of the Cité residences standing sentry along the lake.
One particularly striking sight is when you roll past the Ohio Street underpass. Here you get an unobstructed look at a canyon of towering skyscrapers marching down State Street. Some of the behemoths visible include the neo-Gothic Tribune Tower and the art-deco Chicago Board of Trade Building. For a fun perspective, look straight up through the underpass to see an architectural collage framed against the sky.
Venturing towards Grant Park yields more visual delights. Approaching Buckingham Fountain at dusk lets you take in how the skyscrapers light up as the sun sinks, putting on a dazzling display. Heading south, you'll get postcard-perfect views of historic Navy Pier jutting out into the lake, with vistas of the Ferris wheel's twinkling lights at night.
In the parks lining the path, you can take scenic breaks on benches to contemplate the panoramas. One spot for soaking in the sights is the placement of the iconic Chicago skyline sign at North Avenue Beach. Positioned here, you can align the sign with the actual skyscrapers behind it and capture the perfect photo.
Windy City Wanderings: A Local's Guide to the Best of Chicago - Indulging in Chicago's Famous Deep Dish Pizza
You can't visit Chicago without indulging in the city's iconic deep dish pizza. This decadent, cheese-laden take on pizza is distinctly Chicagoan and a "must eat" for any foodie visiting the Windy City.
Unlike thin crust Neapolitan-style pizza, deep dish pizza has a buttery, crunchy crust that rises two to three inches high to hold generous amounts of toppings. Cheese goes down first, followed by chunky tomato sauce, covering toppings like sausage, pepperoni, onions, mushrooms and more. Each ingredient is layered on thick for a seriously indulgent, almost casserole-like pizza experience.
The original pioneers of Chicago deep dish pizza were Pizzeria Uno and Pizzeria Due in the River North neighborhood. These restaurants claim to have invented the dish in 1943 and still bake deep dish pizzas in cast iron pans for that signature caramelized, crispy crust. Customers rave about the rich, fluffy dough paired with thick blanket of mozzarella for a mouthwatering deep dish delight.
Lou Malnati's is another beloved spot for authentic Chicago deep dish, using a secret family recipe that's been passed down for generations. Their buttery crust, loaded with cheese and toppings, is considered by many to be the gold standard. One Yelp reviewer said the Malnati Chicago Classic with sausage left his taste buds "singing with joy."
For a creative spin, try Pequod's deep dish pizza with its caramelized crust. By baking the underside of the crust longer, it develops a crispy, almost fried texture that people drive across town for. As one blogger put it, each golden-brown bite tastes "like a delectable pizza pot pie."
If you want to sample multiple deep dish pizzas in one go, head to Chicago Pizza Tours. Their guided walking tours take you to different restaurants in Chicago's neighborhoods to taste their unique deep dish pizzas and meet the owners. It's a delicious way to discover the city's pizza culture and history.
Wherever you go for deep dish in Chicago, be sure to wear loose pants and come hungry! The rich dough and abundant cheese make for an incredibly filling meal. Consider sharing a pizza between two or three people. But don't be ashamed to take leftovers back to your hotel – deep dish often tastes even better the next day after the crust has soaked up all the flavors.
Windy City Wanderings: A Local's Guide to the Best of Chicago - Exploring The Art Institute's Impressive Collection
Housing one of the oldest and largest art collections in the United States, the Art Institute of Chicago showcases iconic masterpieces from around the world spanning thousands of years. Wandering the Institute's halls leaves you awe-struck by the sheer breadth of creativity on display.
The highlight for many is seeing Grant Wood's American Gothic on its home turf. This iconic painting depicts a stern-looking farming couple, the man clutching a pitchfork. The work's exaggerated features and realist style have etched it into pop culture's consciousness. Its prominent display draws throngs of visitors seeking selfies with the deadpan couple.
Beyond American Gothic, the Institute houses the world's largest collection of Impressionist and Post-Impressionist paintings outside the Louvre in Paris. Works by luminaries like Monet, Renoir, and Van Gogh adorn the walls. Claude Monet's dreamy haystacks at different times of day demonstrate how light radically alters a scene's mood. Meanwhile, the bold strokes of Van Gogh's Bedroom in Arles immerse you in the artist's turbulent state of mind.
The Paul Gauguin collection stands out for providing insights into the French artist's Free Spirit philosophy. Exotic Tahitian landscapes like Fatata Te Mouà and brooding Breton women portraits like La Belle Angele unveil Gauguin's imaginative, mystical side. His innovative use of color and flattened perspectives created a breathtaking new visual vocabulary.
Beyond Impressionism, the Institute houses the incredible Thorne Miniature Rooms showcasing tiny furnishings from European interiors dating back to the 13th century. Peer down into the Lilliputian world of delicate chairs, chandeliers, and four-post beds all meticulously crafted on a 1:12 scale.
The Modern Wing's airy galleries feature 20th century icons. Picasso's abstract antiwar masterpiece Guernica spreads across an entire wall, conveying raw anguish through disjointed forms. Ironworkers lunching on an I-beam in 1932 demonstrates Charles Sheeler's precisionist style, reducing industrial imagery to crisp geometry. This diversity of artistic styles and periods on display makes the Art Institute a must-visit.
Windy City Wanderings: A Local's Guide to the Best of Chicago - Taking in a Show at Historic Theaters Along State Street
As the lights dim and the velvet curtain rises, you are transported back to the Golden Age of cinema and theater along Chicago’s iconic State Street. This legendary stretch once boasted over a dozen lavish theaters that hosted vaudeville revues, films, and Broadway spectacles in the early 20th century. And though venues like the Chicago Theatre stand as reminders of this glamorous past, a handful of historic theaters still operate today, offering everything from comedy shows to musicals. Capturing a live performance in these storied venues provides an evening of entertainment wrapped in architectural grandeur.
Stepping inside the CIBC Theatre transports you to the Jazz Age with its French Baroque opulence. Originally the Majestic Theatre, this venue hosted variety shows and silent films when it first opened in 1906. Later, it saw legends like Harry Houdini and Mae West grace its stage. In its current incarnation, it hosts long-running productions like The Lion King and Aladdin in an auditorium modeled after the Paris Opera House, complete with crystal chandeliers and gilded detailing. As reviewers rave, seeing a show here feels like “attending the theater in a palace.” Beyond its beauty, the theater boasts excellent acoustics, immersive effects, and contemporary amenities that blend seamlessly with the historic charm.
Just down the block lies the Cadillac Palace Theatre, a lavish movie palace built in 1926 during State Street’s theater boom. Its Baroque plasterwork, massive chandeliers, and sweeping staircase earned it a reputation as the most opulent theater in Chicago. After a multi-million dollar restoration in 1999, the Palace began hosting Broadway musicals and concerts in addition to films. Long-running hits like Hamilton and Dear Evan Hansen have graced its stage, amplifying the theater's grandeur with rousing songs and choreography. This venue also hosts comedy shows, allowing you to laugh uproariously in a setting built for gasps.
For an intimate theater experience, the CIBC Theatre’s sister venue the Royal George Cabaret offers a small black-box theater setting that seats just 180. Though lacking the ostentation of State Street’s other theaters, its cozy, modern atmosphere makes you feel part of the performance. Here you can catch edgy dramas, envelope-pushing sketch comedy troupes, and late-night magic shows in a setting where every seat feels close to the action. The tiny lobby bar lets you mingle with cast members after the show for an insider’s night out.
Windy City Wanderings: A Local's Guide to the Best of Chicago - Wrigley Field: America's Most Iconic Ballpark
With its emerald field surrounded by retro red brick, ivy-covered walls and vintage hand-operated scoreboard, Wrigley Field stands as America’s most iconic and beloved baseball park. As the historic home of the Chicago Cubs since 1916, this lively north side stadium exudes an irresistible, nostalgic charm. Attending a game here feels like stepping back in time.
Unlike sterile concrete behemoths built recently, Wrigley retains an early 20th century intimacy and quirkiness. Seats are snugly packed along the baselines, putting fans practically on top of the action. Columns holding up the upper deck and crisscrossing steel supports provide obstructed sightlines but add old-timey character. The hand-turned scoreboard in center field still relies on workers manually updating scores on metal plates – a wonderful contrast to today's high-tech video boards.
When the wind blows off Lake Michigan, the red and white flags ripple atop the iconic scoreboard. The gusts swirl around the open-air stadium, affect play, and give the Cubs their “wind advantage.” On lazy summer afternoons when Wrigley’s old-growth ivy blooms green, you feel transported back to a simpler era of baseball.
Beyond its throwback aesthetics, the electric game-day atmosphere at Wrigleyville captivates visitors. Fans fill the streets before first pitch, socializing at Murphy’s Bleachers sports bar or partying on residents’ rooftops overlooking the field. Inside, ear-splitting cheers and chants echo as devotees live and die with each Cubs pitch. The seventh inning stretch brings the entire crowd to its feet belting out "Take Me Out to the Ball Game." Wins unleash euphoric celebrations while losses elicit pained groans. But the shared camaraderie of Cubs fans – win or lose – makes attending a game at Wrigley Field an unforgettable experience.
As one diehard fan put it, “Wrigley Field is more than a ballpark, it’s a communal gathering place.” First-time visitors invariably remark how the lively atmosphere and old-fashioned environs make them instant Cubs devotees. Ballplayers too revere Wrigley Field’s aura and privileged status as the National League’s second oldest park. As former Cub Kerry Wood described, “There’s just an energy and atmosphere you can’t find anywhere else.”
Windy City Wanderings: A Local's Guide to the Best of Chicago - Visiting The Local Favorites in Vibrant Wicker Park
Beyond downtown, Chicago’s distinctive neighborhoods buzz with their own charms worth exploring. In particular, the creative energy and casual cool of Wicker Park lures visitors to stroll its leafy streets and sample local flavor. With indie boutiques, hip bars, and buzzed-about eateries, this Northwest side enclave delivers a quintessentially Chicago mix of art, culture and culinary delights.
Grab a coffee at Wormhole Coffee then window-shop along Milwaukee and North Avenues to see hot emerging designers. Homegrown lines like Akira showcase women’s wear mixing streetwear edge with feminine accents. Shop McFadden & Hoof for handcrafted leather bags and Gallery M for stylish housewares, all crafted locally. Don’t miss Myopic Books, a beloved used bookshop spanning three dusty floors - expect to unearth quirky first editions or obscure academic tomes whilst chatting with the warm owner.
Refuel at Big Star, the taco joint that kickstarted Wicker Park's dining renaissance. Their al pastor and fish tacos paired with margaritas on the lively outdoor patio capture the neighborhood’s casual spirit. Or join the crowd waiting outside Dimo’s Pizza for their perfectly blistered crusts topped with creative ingredients like jerk chicken or mac n’ cheese. Finish with donuts from Stan’s, a neighborhood fixture serving piping hot old-fashioneds, yeast-risen classics and maple bacon delights.
Experience Wicker Park after dark at Violet Hour, an intimate speakeasy requiring a password for entry. Settle into a worn leather booth beneath the antique crystal chandelier to sip expertly crafted cocktails as jazz plays softly. Those seeking a rowdier scene can hit Queen Mary, a party boat permanently docked on the neighborhood’s edge, or Late Bar, renowned for staying open until 5am.
On weekends, stroll along Wicker Park’s leafy paths to burn off the previous night's excess. Grab a cone at Brgrbelly then scope out street art covering the walls and sidewalks. Striking murals celebrate Latino culture along Division Street while eclectic works by local artists bring visual vibrancy to the area's many underpasses. Stop by Wicker Park's eponymous green space to people watch beside the iconic iron “Chicago” entrance sculpture.
Windy City Wanderings: A Local's Guide to the Best of Chicago - Discovering Chicago's Diverse Neighborhoods on Foot
Beyond the hustle of downtown, Chicago’s 77 distinct community areas burst with diversity, history, and local character best discovered on foot. Meandering side streets lined with mom-and-pop shops, wandering leafy residential blocks, and chatting with locals unveil each neighborhood’s spirit in a way driving cannot.
Strolling through Pilsen provides a window into Mexican culture and artistry woven into daily life. Vibrant murals by local artists cover once-drab walls, transforming the area into a vivid open-air gallery. On 18th Street, shop handmade textiles at the Fashion Outlets then grab a tres leches cake from La Casa Del Pueblo. The National Museum of Mexican Art houses the largest Mexican fine art collection in the U.S. for free.
In Chinatown, hopping between the aromatic bakeries, bubble tea cafes, import shops and steaming barbecue joints along Wentworth Avenue makes you momentarily forget you’re stateside. Catch senior citizens socializing in Ping Tom Memorial Park or glimpse practicing lion dancers through a community center window to see Chinese traditions thriving. The Pui Tak Center offers guided walking tours expounding on the neighborhood’s history.
Meandering the residential streets of Hyde Park transports you back to the early 1900s birth of modern architecture. Marvel at the low-slung, geometric lines of Frank Lloyd Wright’s Robie House then stroll past stately Victorian homes neighboring the University of Chicago campus. The Museum of Science and Industry delights all ages with interactive science displays.
Andersonville’s cozy cafes, gastropubs and boutiques catering to the LGBTQ+ community exude an inclusive, progressive vibe. Stop by Women & Children First, the country’s oldest feminist bookstore, before browsing musical instruments at the Chicago Music Exchange. Grab a beer at atmospheric Simon’s Tavern, favored by renowned storyteller Jean Shepherd in the ‘70s.
In Bronzeville, the “Black Metropolis,” visit historical sites interweaving African American life, arts, and culture. Git in the Rezone groove during a soul food brunch at vibey Pearl’s Place before walking the Black Metropolis Landmark District. Here, the Victory Monument by sculptor Elizabeth Catlett honors labor movement heroes. Gain perspective at the Chicago Bee Building on the influential Black-owned newspaper.