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.

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

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.

The Peninsula, which opened in 2001, is without a doubt Chicago’s most visually stunning hotel, featuring a sun-filled, fifth-floor lobby restaurant with soaring 20-foot windows, sophisticated guest rooms done in luxe cream and deep blue fabrics and an enormous pool surrounded by teak lounge chairs. The décor is fresh, modern and gorgeous, and the amenities are top-of-the-line.

The 339 guest rooms are full of tech-forward luxuries, like charging cords built into the nightstands and brand-new tablets in 11 languages that allow guests to control the temperature, television and lighting. These easy-to-use gadgets are also loaded with more than 2,000 international publications, information on local attractions and room service menus, essentially negating the need to ever get out of bed.

Guests can unwind at the 15,000-square-foot spa, which has eight treatment rooms and an enticing Quiet Room, where they can lounge on plush chaises near the flickering gas fire. The fitness center has fantastic views of the city and lake, and the 30 weekly classes on offer include yoga and Pilates. Summer visitors will relish the south-facing sundeck next to the pool.

In addition to serving breakfast, lunch and afternoon tea, the Lobby restaurant has a fun late-night scene.

Talk to the concierge about the customized cultural excursions available through the “Keys to the City” program, from access to the VIP intermission lounge at Broadway in Chicago performances to private kitchen tours at spectacular restaurants.

Situated in downtown Chicago, where The Loop meets the Magnificent Mile, The Langham’s outstanding location is just one of its many perks. 

Set in a renovated bank building, Virgin Hotel Chicago is a modern retreat in downtown Chicago spanning over 25 floors. Though the lobby is small, a grand staircase leads to the buzzing Commons Club, the hotel’s lounge that hosts a daily social hour for guests, as well as the Upside Down Tea Party, a boozy take on traditional afternoon tea. After entering the chic lobby, guests can check in at the front desk or at one of the many iPad kiosks.

Sleek hallways lead to Virgin’s 250 guest rooms, referred to as chambers. The minimalist accommodations are spacious and decorated in neutral tones punctuated with Virgin’s trademark red accents. All chambers feature the patented “Virgin Lounge Bed,” a mini Smeg fridge stocked with fair-priced beverages and snacks and a yoga mat for in-room fitness. The spacious, all-white bathrooms have double sinks and mirrors and oversized showers. The hotel even has its own app called Lucy, which handles all aspects of guests’ stays from city recommendations to setting the room temperature.

The rooftop bar, Cerise, has panoramic views of the city and hosts DJs and live music on weekends. The hotel also houses Miss Ricky’s, an upscale diner that serves classic comfort foods for breakfast and late-night bites. For working off indulgences, there is also a rooftop gym and a spa.