Destination Guide


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Courtesy Adam Alexander Photography

With top-of-the-line hotels and shopping, gorgeous architecture and a world-famous skyline, plus one of the most exciting dining scenes in the country, the Windy City is one of America’s most exciting cities. Best of all, you can count on an exceptionally warm welcome and friendly service wherever you go.


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Living Room at Chicago Athletic Association Hotel, Chicago, Midwest - Courtesy Alan Shortall

Chicago Athletic Association Hotel

Located across the street from Millennium Park, the hip Chicago Athletic Association Hotel is located in one of Chicago’s most architecturally significant buildings. Originally designed to look like a Venetian palace, the CAA was founded in 1890 as a men’s club for athletic, business and social pursuits. It closed in 2007 and reopened in 2015 with 241 restored rooms and a preserved landmark feel.

The boutique property is awash with such historical details as fencing court floorboards lining the elevator walls, ornate mosaic-tiled floors and stained-glass windows. The lobby-lounge looks a bit like a Brooklyn hipster went to town on a Harvard study, albeit in an ultra-cozy and appealing way: leather Chesterfield sofas, rich Persian carpets and carved stone fireplaces are the defining characteristics here. The rooms are a touch more subdued, with crisp white Sferra bedding, brass-accented bed frames and Carrara marble bathrooms, plus plenty of references to the building’s past life (pommel horses, shelving that was once a climbing rack, et. al). It is worth noting that the Standard rooms are, as one might expect, not as chic as the upper level rooms. They are a bit dark and have windows that open up to the backside of another building.

The hotel’s much-hyped restaurants and bars attract a cool crowd of Chicagoans. The jewel in CAA’s culinary crown is Cindy’s, the 13th-floor rooftop eatery and lounge that is a magnet for the after-5pm clique; blame it on the outside terrace with fire pits and amazing views of Millennium Park, the craft punch cocktails or the seasonal Midwest comfort food. Though windowless, Cherry Circle Room is a charmingly retro eatery with cherry paneling and cabinetry housing an impressive wine collection. The 15,000-square-foot Game Room off of the lobby acts as a playground for kids during the day and young professionals at night with entertainment such as bocce, shuffleboard, chess and more.

The CAA doesn’t want for eating and drinking establishments, and is well equipped in terms of amenities as well, including 24-hour room service and fitness facilities (fittingly enough), Heritage Bicycle rentals and complimentary WiFi.

Lounge at Four Seasons Hotel Chicago, Chicago, Midwest

Four Seasons Hotel Chicago

Being the closest luxury hotel to Lake Michigan, the Four Seasons offers magnificent views of the water, plus dependably excellent service and amenities.

Executive Suite at Park Hyatt, Chicago, Midwest

Park Hyatt Chicago

With spacious rooms and a sizable art collection, the Park Hyatt is smart and comfortable. Though the lobby is located at street level—a rarity in Chicago—it has a serene feel, with a minimalist-chic check-in area and, off to the side, a cozy living room with couches and complimentary tea available throughout the day.

The property is currently undergoing a massive renovation and will be closed until spring 2022. This long overdue facelift includes both cosmetic and foundational updates. We can expect to see lighter decor, technological advances and additional suite room categories.

The NoMI Kitchen and Lounge on the seventh floor serves contemporary American cuisine with locally sourced ingredients. With its wall of windows that tilts out over historic Water Tower Place, there are far worse places in Chicago for a business lunch or a pre-dinner cocktail, and the popular deck welcomes al fresco diners during the warmer months. Also on this floor is a beautiful three-lane pool and intimate spa.

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