Designed in the Beaux-Arts style by noted Chicago architect Alfred S. Alschuler and completed in 1923, the 23-story London Guarantee & Accident Building stands at the corner of Michigan Avenue and Wacker Drive. The former office building reopened in 2016 as the 452-room LondonHouse hotel. The $200 million project retains the property’s original gold-leaf ceilings and murals. The hotel’s roof terrace remains a popular spot during Chicago’s warmer months and it has a great view of significant architecture along the river.

This 1893 Venetian-Gothic style building by architect Henry Ives Cobb housed the private Chicago Athletic Association club until 2007. A 2015 redevelopment transformed the Michigan Avenue structure into a boutique hotel with 241 guest rooms. Now, the Chicago Athletic Association preserves much of the historic club’s architectural details including an ornate wood-trimmed lobby and a plaster ballroom. A rooftop restaurant and bar offers stunning views of Millennium Park and Lake Michigan.

Standing like an oversized champagne bottle topped by gold foil, the 1929 Carbide & Carbon Building is a true Chicago icon. Designed by the Burnham brothers, the Art Deco building shifted from office space into the Hard Rock Hotel in 2004, which predates most conversions on this list. In 2017, the Hard Rock shut down and the space was turned into the St. Jane Hotel—named for Chicago-based social activist Jane Addams.

This landmarked office tower at the corner of Lake and Wabash opened in 2015 as the Virgin Hotel following a three-year renovation. The Old Dearborn Bank Building was completed in 1928 by architecture firm Rapp & Rapp, which was known for designing some of Chicago’s best-known movie palaces. The historic exterior conceals a playful contemporary interior topped by an indoor-outdoor rooftop lounge.

Built in the heart of the Loop’s financial district in 1894 by celebrated architect and engineer William Le Baron Jenney, the 14-story New York Life Insurance Building outlived its life as an office. Thankfully, after a push by local preservationists to landmark the property, the historic tower turned into the 293-room Kimpton Gray Hotel in 2016. The redevelopment repaired exterior brick and terracotta details, replaced aging windows, and restored interior marble to its 19th-century glory.

This 35-story LaSalle Street landmark was built between 1915 and 1925 by architecture firm Holabird & Roche. It is considered Chicago’s best example of Portuguese Gothic Revival. After decades of office use, the Roanoke Building was made into the world’s largest Marriott Residence Inn in 2015. The repositioned property includes 380 extended stay guest rooms and 7,500 square feet of meeting space.

Constructed in the late 19th by Architects Daniel Burnham, John Root, and Charles Atwood, the Loop’s Reliance Building features a steel frame with a white glazed terracotta exterior and was the first high-rise to incorporate large plate glass windows. In 1999, the building underwent a major restoration and opened as the 122-room Hotel Burnham. The hotel portion later sold and was rebranded as the Staypineapple.

In Wicker Park, the 203-foot-tall former Northwest Tower (also known as the Coyote Building) has loomed over the intersection of Damen, Milwaukee, and North avenues since the 1920s. Despite its impressive stature, the offices fell into disrepair. That all changed in 2016 after the property reopened as the 69-room Robey hotel. The refurb restored many of the Art Deco touches designed by original architects Perkins, Chatten, and Hammond and added two rooftop bars with sweeping skyline vistas.

The transformation of Fulton Market’s Allis Building from a five-story loft warehouse into the trendy Soho House hotel and private club proved that vintage industrial buildings are equally suited for hospitality roles. The 2014 adaptive reuse recreated the 1907 building’s original entryway mosaic and incorporated planks from its demolished rooftop water tower into artwork in the lobby.