The Windy City - Chicago, IL
Spectacular skyscrapers, renowned museums, and one of the world’s greatest symphony orchestras, Chicago sits on Lake Michigan, Illinois in the heart of the American Midwest. Aptly nicknamed the Windy City, it’s a wonderful place to spend a weekend away. There is something for everyone in this City, which is one of the U.S.A.’s most popular tourist destinations.
Dream
We like to stay in a hotel in close proximity to the Magnificent Mile, in either the River North neighborhood or the Loop. That way we are within easy reach of Chicago’s premier downtown shopping, restaurants, tourist sites such as the river walk at Wacker Drive, Millennium Park and many cultural institutions the city has to offer.
Four Seasons: Just steps from Michigan Avenue and within the same building as the upscale 900 North Michigan Shops, the hotel offers everything you would expect from this luxury brand, including a well-equipped gym with Peleton bikes. It is situated across the street from the distinctive John Hancock building, one of the City’s signature skyscrapers, which conveniently sits atop a Starbucks café and Cheesecake Factory restaurant.
Chicago Athletic Association Hotel: Across from Millennium Park in the Chicago Loop neighborhood, this hotel is set within a Venetian Gothic landmark building dating from 1893, transformed into a funky hotel which opened in 2015. Formerly an elite private members’ club, interior designers Roman + Williams have made frequent references to the building’s historic sporting past and even reused original elements such as the old squash-court flooring that lines the elevators. There’s a Shake Shack in the lobby, and a high-quality Fairgrounds coffee shop. But the highlight is the spectacular 180-degree lakeshore view from Cindy’s, the hotel’s rooftop bar and restaurant.
Dine
Gilt Bar, River North: Across the street from the cavernous Merchandise Mart, this dimly lit bar and restaurant has the air of a Prohibition-era speakeasy. The menu is contemporary American cuisine and the gilded bar dispenses an extensive list of craft cocktails.
Avec, West Loop: This compact, minimalist style restaurant with communal seating and a chef’s counter serves an inventive and eclectic range of Mediterranean style small plates. Opened in 2003, the high-quality fare served up by celebrity chef Paul Kahan has made this place a Chicago mainstay.
Little Goat Diner: This retro eatery, the sister restaurant of The Girl and the Goat, is their celebration of the Classic Diner. It serves an array of American comfort food, sandwiches and all-day breakfast, in a setting reminiscent of the 1950’s.
RL Restaurant, River North: Ralph Lauren’s upscale eatery on Michigan Avenue, with a bar at the front and separate dining room beyond, serves classic American dishes in a slightly starchy club atmosphere, replete with brown leather chairs, wood-paneled ceiling, antique pictures and a smart business casual dress code.
Do
Chicago Symphony Orchestra: One of the World’s greatest orchestras, currently led by Italian Riccardo Muti, has its home at Orchestra Hall on Michigan Avenue, across from Millennium Park. This opera house style hall is one of the best in the U.S.A., with excellent sight lines due to its steeply sloping balconies, and fantastic acoustics.
Art Institute of Chicago: Located on Michigan Avenue at Millennium Park, this is one of the premier art museums in the U.S.A. Notable exhibits include the evocative Nighthawks by Edward Hopper, painted in 1942 and inspired by a restaurant on New York’s Greenwich Avenue, and the beautiful American Windows by Russian-French artist Marc Chagall.
Architecture Boat Tour: This is one of the highlights of any visit to Chicago. The 90-minute cruise around the Chicago River is operated by the Chicago Architecture Foundation. During the tour, CAF-certified tour guides interpret more than 50 buildings highlighting Chicago’s growth from a small settlement into one of the World’s largest cities. Note: if the wind blows be sure to wear several layers!
Walk in Millennium Park: This huge public park located in the Loop, is a reimagined section of Grant Park on Michigan Avenue, originally intended to celebrate the third millennium. The park opened in 2004 and recently became the top tourist destination in Chicago and the entire Midwest, attracting an estimated 25 million plus visitors per year. Notable attractions within the park are the Jay Pritzker Pavillion, an outdoor performance space designed by Frank Gehry, the BP Pedestrian Bridge, also designed by Gehry, and the immensely popular Cloud Gate stainless steel sculpture designed by Anish Kapoor, better known as The Bean!
Visit Oak Park: This village adjacent to the West side of the City was home to the American master architect and proponent of the Prairie School, Frank Lloyd Wright from 1889 to 1911. The neighborhood, which is easily reached from downtown Chicago via the “L” train system, contains the largest collection of Wright-designed residential properties in the world. Also of interest to architecture and design fans are the architect’s home and studio, which are open to visitors, and the Wright designed church, the Unity Temple.