Less Bluster, More Bustle Finding Your Way in the Windy City

My first introduction to the city of Chicago was the 1995 film While You Were Sleeping. B-roll of the city’s skyline flashed through the movie, and the clickety-clack of the “L” ran through its soundtrack. A silver caterpillar cruising over bridges, past the Chicago River. Home to two and a half million people, the city boasts some of the most popular tourist destinations in the world. Parks, hotels, river walks and cruises: enough to fill a day, a weekend, or even a couple weeks of fun filled romping around The Windy City.

Cloud Gate
Photo by Adam Alexander Photography

Located in the heart of downtown Chicago, Millennium Park showcases world-class architecture, the most sophisticated outdoor concert venue of its kind: an award-winning center for art and music designed by Frank Gehry. Bordered by Michigan Avenue to the west, Columbus Drive to the east, Randolph Street to the North, and Monroe Street to the South: a virtual hotbed of activity any way you walk. Conceived as an outdoor space by then-mayor Richard M. Dayley, the plan evolved from a 16-acre park to the 24.5-acre triumph in the tradition of the city’s original founders.

Rising 1,353 above the streets of the Windy City, The Ledge is a transformative viewing experience. Not for the faint of heart, it’s glass boxes extend 4.3 feet beyond Willis Towers’ Skydeck on the 103rd floor, providing a rarely seen view of the city. The original Sears Tower architecture firm (Skidmore, Owings and Merrill) designed The Ledge so that the fully enclosed glass boxes retract into the building, allowing access for maintenance – and to keep the glass as crystalline as possible. Standing 110 stories tall, the tower itself is a world renowned feat of architecture. Being out on a glass ledge, over a thousand feet above the deck, you’ll never see Chicago with the same eyes again.

Chicago Riverwalk
Photo by Ranvestel Photographic

Ninety minutes isn’t that long. A typical Hollywood blockbuster runs exactly that – excluding credits and previews, of course. And yet, so much can happen in an hour and thirty minutes. Daily during the sailing season, discover the luxury of Chicago’s finest fleet, and hop aboard for 90 minutes of amazing. Choose Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises to experience a river cruise from the Riverwalk, just three blocks north of Millennium Park. Complete with open-air decks and interior salon room, full bar service, and catering based on your group attendance, you can experience the city in a brand new way. Choose a private cruise for your company, wedding party or social engagement and travel beneath the city’s magnificent skyline alongside a CAF-certified volunteer docent providing stories of The Windy City’s original architects. Magic on the water, in just 90 minutes.

Chicago Skydeck
Photo by Adam Alexander Photography

Many modern cities exist solely because their original inhabitants needed a place near the water to survive, a great many years ago. Chicago is no different, and in fact, the history of the city side by side its greatest river makes for some of the most fascinating reading out there. The Chicago Riverwalk offers an in-person look at the city from one of its most unique angles. Dining opportunities, public art exhibitions, local musicians and special events are hosted throughout the season. Tours of the bridges, birding walks with Audubon Great Lakes, and the McCormick Bridgehouse and River Museum offer up some of the city’s most incredible activities side-along its historic landmarks.

Photo courtesy of City of Chicago

CityPASS Chicago

Experience the best of Chicago with CityPASS. You’ll get VIP admission to the most iconic attractions in the city, hand-picked and packaged into one convenient ticket booklet at a big savings (54% off on VIP admission to 5 of Chicago’s top attractions).

Field Museum of Chicago

SUE is the largest, most complete, and best-preserved Tyrannosaurus rex in the entire world (and the most iconic exhibit in the Field Museum). Like most boys his age, my 10-year-old (and his Daddy, for that matter) haven’t outgrown the fascination with all things dinosaur. From the tip of her snout to the tip of her tail, SUE measures 40.5 feet long. Though her skeleton greets you right when you walk in Stanley Field Hall, the skull atop the skeleton is a replica (the original 600-pound skull sits in a display on the Museum’s balcony, beneath a mural of what SUE might have looked like before she was a fossil). From dinosaurs (Evolving Planet) and mummies (Inside Ancient Egypt) to the Underground Adventure (where you shrink down to the size of a bug), you can easily while away an educational afternoon here.

Adler Planetarium and Astronomy Center

Be transported to the outer reaches of the Universe on a visit to Chicago’s Adler Planetarium and Astronomy Museum. Opened in 1930, Adler bears the distinction of being the first planetarium in the United States. On your self-guided tour you’ll visit the historic Atwood Experience identifying the positions of the brightest stars in the night sky and constellations they form. You’ll also visit Shoot for the Moon, highlighting the exciting stories of space exploration and America’s bold plans to travel to the Moon.

All they really had to say were the words “free evening wine hours,” and I was in. Not a wine drinker? How about being within walking distance to the Cadillac Place Theatre, or Millennium Park, or Willis Tower? Or the fact that its location, in the heart of Chicago’s Theatre District, is surrounded by the Loop’s foremost sights – including Grant Park and State Street’s shopping Mecca. Perhaps it’s the mere mention of 312 Chicago (for more info, see Chicago Eats/Dining Destinations) or Bar Allegro (voted one of the “Coolest Hotel Bars in Chicago” by Michigan Avenue Magazine), with its delicious small bites and cocktails. Each add up to just one thing: America’s Golden Era is alive and well at the Kimpton Hotel Allegro (www.allegrochicago.com).

Revamped Chicago Loop Boutique: Kimpton Hotel Allegro
Photos by Cris Molina

The simple, yet sophisticated elegance of this historic boutique haven harkens back to an era of elegant hobnobbing and glamour (think mid-century moxie and old school glamour with a modern twist) – its accommodations are classically stylish, super comfy, amenity-rich (on-demand movies, designer toiletries, in room spa services or free in-room yoga accessories) with the added perks of a hosted social hour in the hotel’s lobby living room from 5 pm – 6 pm nightly, complimentary newspapers and morning coffee and tea service daily. The friendly, helpful staff are at the ready to show guests what Chicago is made of. And if you have a little wine on the side, so be it.

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