Calling all Art Deco lovers! This high-rise was originally built in 1929 and designed by Perkins, Chatten, & Hammond. Instead of an office building, its now an 89-room hotel with dark, moody interiors, two rooftop bars, and a small pool. It’s right at the center of Wicker Park and Bucktown so all the shopping, restaurants, and bars are just a few steps away.

After it opened in 1926, the Ambassador Chicago was soon beloved by Frank Sinatra, Marilyn Monroe, Elizabeth Taylor. The celebrities were known to hang out in the legendary bar the Pump Room, now called Food Gallery. The most notable feature of the hotel is the highly detailed and extravagant Art Deco lobby: vaulted ceilings, original crown molding, glass door knobs, ornate wrought iron, and 1920s mail chutes. By staying here, you’ll be surrounded by the city’s other landmarks on like Chicago’s Water Tower.

The Drake Hotel was designed by architect Benjamin Howard Marshall in an Italian Renaissance style and opened on New Years’ Eve in 1920. The hotel quickly became a place for the elite to gather, rivaling competitors with several restaurants, including the well-known Cape Cod Room, and two large ballrooms. Afternoon tea has been served in the Palm Room, originally the Fountain Court, for nearly a century (Princess Diana was a visitor). In the ’40s the room would change in summer: the ceiling would open up and a large fountain was brought in, and the winter centerpiece was a 2,000 pound fireplace.

The Warwick Allerton opened as a social club and hotel in 1924. Club hotels in the ’20s catered to single young men and the Allerton had a library lounge, private dining rooms, a barbershop, a solarium, a miniature golf course, and squash courts. Located in a neighborhood of 19th century row houses, the hotel was also designed to look like a home. The work of New York’s Murgatroyd & Ogden featured dark red brick walls, round-arched windows and arcades, and a sculptural rooftop.

The hotel today consists of two towers, a north tower built in 1961 and a historic south tower built in 1929. The latter was formerly the Medinah Athletic Club and commissioned by the Shriners organization. The architect Walter W. Ahlschlager pulled from many different architectural styles. The exterior featured Assyrian style carvings, some of which can still be seen today, and a Moorish gold-painted dome. The 120,000-gallon pool was put on the the 14th floor, which was the highest indoor pool at the time, and decorated in blue Spanish majolica tiles with a terra-cotta fountain of Neptune. While many of the hotel’s original club features have been lost, the pool remains very much the same.

The Beaux Arts LondonHouse Chicago stands regally at the south bank of the Chicago River. The hotel was the result of a $200 million renovation of the 1923 Alfred Alschuler-designed London Guarantee & Accident Building. It sits at the former site of Fort Dearborn, which played an important role in early Chicago history. There’s a bronze relief that depicts the military fort above the main entrance and in the lobby a two-story colorized portrait of General William Hull greets guests.

The polished, black granite Carbide and Carbon building on Michigan Avenue was completed in 1929 by the Burnham Brothers, sons of the famed Chicago architect Daniel Burnham. Legend has it that the duo designed the building to resemble a champagne bottle with gold foil covering the top tower, a bold and boozy statement during the Prohibition era. It was transformed into the Hard Rock Hotel Chicago in 2001 but reopened in 2018 as the St. Jane Chicago Hotel, named for Nobel Peace Prize-winner and Chicago-based social activist Jane Addams.

Housed in a 110-year-old historic building, this tiny 11-room boutique hotel has clawfoot tubs, vintage rugs, expansive windows, and leafy tropical plants. Plus, this West Loop location will mean your within walking distance of the city’s most hyped dining scene on Randolph Street. Staying at this rehabbed bed and breakfast will also give you a chance to experience some of the neighborhood’s historic charm—which is quickly disappearing with so many new buildings on the horizon.

The 14-story Reliance Building was considered one of the city’s first skyscrapers in 1895. Architects Daniel Burnahm, John Root and Charles Atwood all worked on the building’s design which included steel, glass and white glazed terracotta. Before it was the Alise Hotel, the building mostly held offices including the dentist of Al Capone. In 1970 the building was recognized as a landmark, but the building was in need of a restoration and a debate about what to do prolonged any action. Eventually in 1999 and with $27.5 million it was renovated into a luxury hotel.

The first Palmer House was touted as the largest hotel in the world, but what currently stand is actually the third incarnation of Potter Palmer’s dream hotel. The first hotel, which burned down in the Great Chicago Fire, was a wedding gift to Bertha Palmer. It was quickly rebuilt and reopened in 1873 making it one of the longest operating hotels in the country. Bertha Palmer was a friend of Claude Monet, and at one point the hotel had the largest collection of impressionist art outside of France. Chandeliers, candelabras, and a ceiling fresco by French painter Louis Pierre Rigal make this quite elegant.

The Congress Plaza Hotel opened in 1893, just in time for the many visitors of the World’s Columbian Exposition. When it opened there were still cobbled streets, gaslights and horse drawn carriages along Michigan Avenue. The building was originally designed as an annex to the Auditorium Theater across the street and linked by an underground marble tunnel called Peacock Alley. The hotel and theater both have a reputation for being quite haunted.

The Blackstone was known in the past for hosting celebrity guests, particularly government officials. The Michigan Avenue hotel has had 12 U.S. presidents as guests since it opened in 1909. If you’ve ever heard someone talk about a decision that was made in smoke-filled room, well, that phrase was coined at The Blackstone. It refers to how Republicans eventually chose Warren G. Harding as their nominee, after many indecisive votes at the convention, a group met privately in room 404 at The Blackstone to choose a candidate.

The Second Empire-style Wheeler Mansion was built in 1870 for Calvin T. Wheeler, a banker and member of the Chicago Board of Trade. Designed by architect Otis T. Wheelock, the home changed hands several times, and even served as a warehouse for the Murphy Butter & Egg Company. In 1997, Debra Seger acquired the landmark property for $10,000 and transformed it into the elegant boutique hotel that it is today.  

The stately Welcome Inn Manor Bed and Breakfast was built in 1893 for Samuel Karpen, a Chicago furniture magnate. The former Queen Anne style home is filled with original art and vintage furnishings, so it’ll feel like a true South Side mansion getaway. Owner Mell Monroe lovingly restored home and offers tours of nearby historic districts, jazz clubs and neighborhoods upon request.