I have packed my winter coat each time I’ve traveled to Chicago and never once has it left my bag.
I’m not sure if it’s good timing or pure luck — perhaps a little of both. But the handful of times I’ve set foot in the Windy City, I’ve meandered its seemingly infinite streets under brisk, blue, cloudless skies. Despite the cold and bitter weather rap Chicago often gets, the biting side of her reputation is something I’ve happily avoided in my strand of late fall travel fortunes.
In this bustling city that sits on the shores of Lake Michigan, the weather is cool but not yet frigid. The sun shines brilliantly, keeping any evidence of winter’s weather at bay. Before Thanksgiving arrives, Christmas will begin to peek through in the whimsically decorated holiday window displays at Macy’s State Street and Chicago’s Loop will glow with twinkling trees. I know by the time evening rolls around, I will have once again fallen for Chicago, in awe of her bright lights and towering buildings and enraptured by the unfettered energy that crackles through her downtown blocks.
Chicago is a city that requires no agenda. And for a traveler without one, this Midwestern metropolis becomes a playground bursting with architectural charms, a rich history, public art displays, shopping and culinary delights.
With fall’s fair weather on my side once again, I blaze out of the River North district’s Amalfi Hotel wrapped in a light scarf and emboldened with a credit card with no real plans other than to while the morning away on the 13-block Magnificent Mile (www.themagnificentmile.com). Nearly 500 department stores, designer shops and posh boutiques line the streets. It’s a happy haven for fashionistas with stores such as Gucci and Louis Vuitton, but also a place for the bargain hunters, outdoor-lovers and shopping newbies thanks to shops such as Forever 21, Patagonia and the LEGO Store. But I’m not a shopaholic with an endless budget so when browsing and buying begins to lose its appeal, I’m thankful other options sprout from every direction.
The Magnificent Mile teems with around 200 restaurants, luring in famished shoppers with enticing smells of fresh-brewed coffee on one corner and deep-dish deliciousness on the next. It only took one trip to realize Chicagoans reserve the same strong opinions about their prize-winning pizza as Austinites do for their beloved tacos. I’m faced with indecision on North Michigan Avenue sandwiched between two of the city’s favorite pizza joints: the Original Gino’s East, which claims to be No. 1 in the what some dub the pizza capital of the world, and Giordano’s on Rush Street, where we waited the better part of two hours to indulge in one of its famous stuffed deep-dish pizza pies worth every passing moment of hunger. Just a few blocks away sits Pizano’s Pizza and Pasta, where red-checkered tablecloths and a warm Italian ambiance create a worthy setting for tucking into the authentic pies that patiently bubble under its toasty brick oven. In a city where pizza joints are as common as coffee shops, I grab a steamy Americano and set off on foot to satisfy my evolving interests — and walk off the calories — toward some of Chicago’s nearby attractions.
It’s no secret this is one of the country’s most architecturally inspiring cities, and one of the best places to take it all in can be found in its downtown heartland. A short trek south along Michigan Avenue leads to Millennium Park (www.millenniumpark.org), the nearly 25-acre art, music and design mecca.. Here a breathtaking combination of architecture, sculpture and landscape design are at play, creating a stunning backdrop for hundreds of annual programs, concerts, exhibitions and public events.
Millennium Park is not only home to Frank Gehry’s Jay Pritzker Pavilion, the 120-foot-high outdoor concert venue marked by its billowing headdress of brushed stainless steel ribbons and overarching trellis of woven steel pipes, but also the BP Bridge, the first Gehry-designed bridge that links Millennium Park with Daley Bicentennial Plaza and the lakefront park system. While wandering through this urban gathering space, don’t miss the chance to pass beneath Cloud Gate, British artist Anish Kapoor’s 110-ton elliptical sculpture that reflects the city’s iconic skyline in its highly-polished 66-foot-long, 33-feet-tall bean-shaped surface. Steps away is Spanish artist Jaume Plensa’s interactive Crown Fountain — two 50-foot glass brick towers emerging from the ends of a reflective pool projecting video images of 1,000 Chicago faces. Starting in mid-November, you can even ice skate in Millennium Park for free, minus the $10 skate rental, at the McCormick Tribune Ice Rink at the intersection of Michigan and Washington.
Also in the area is the Art Institute of Chicago (www.artic.edu), located on the edge of the sprawling 319-acre Grant Park. The museum is the country’s second-largest and houses one of the nation’s most impressive collections of Impressionist and Post-Impressionist art with an astounding 300,000 works of art in its permanent collection. A 2-mile walk or seven-minute cab ride will take you to Navy Pier (www.navypier.com), the fun-filled 50-acre lakefront playground featuring attractions such as a 150-foot Ferris wheel that gives way to stellar views of the city, an 18-hole miniature golf course, the Chicago Shakespeare Theater and countless free public shows and concerts year round.
But I’ve found one of the best ways to wrap up an autumn evening in Chicago is with a cocktail in hand and an unparalleled view of the city. I find my way to the 100-story John Hancock Center, where there is nowhere to go but up. From a window seat in the bar of The Signature Lounge at the 95th floor (www.signatureroom.com/TheSignatureLounge), I absorb a phenomenal bird’s eye view of the city’s endless stream of glimmering lights and towering buildings that cast their shadows over Lake Michigan. Here, looking out on all of Chicago, I know I have barely breached the surface of what this spectacular metropolis has to offer. And while I may still be a stranger to her cold winters, I am grateful to have experienced her warmth.