Historic Chicago Hotels

Who can forget the opening scene of “The Untouchables,” when notorious and feared Chicago mobster Al Capone was being shaved, got nicked, and cast a menacing glare at his barber? The movie and the scene were purely works of fiction, but an actual barbershop frequented by Capone can be visited today at one of Chicago’s famous historic hotels.

Many of Chicago’s most historic hotels opened during the Prohibition Era. The site of Capone’s favorite barber, The Blackstone, opened a bit earlier in 1910 and also played host to Lucky Luciano’s National Crime Syndicate in the Crystal Ballroom. It’s registered on the National Register of Historic Places. Other historic hotels such as the Millennium Knickerbocker Hotel, the InterContinental Chicago, The Drake, and the Allerton Hotel, all opened in the 1920’s and may have had their brushes with infamy.

However, not all of these hotel’s histories are of a nefarious nature. The Blackstone also hosted 12 U.S. Presidents, Truman Capote, Joan Crawford, and Rudolph Valentino. The Drake saw its share of Presidential guests and such eminent people as Amelia Earhart, Walt Disney, Princess Diana, and both Frank Sinatra and Dean Martin of the “Rat Pack.”

The very oldest hotel in the Loop is The Palmer House Hilton Hotel built in 1871. A victim of the Chicago fire, the Palmer House was rebuilt despite being destroyed only 13 days into its initial opening. Its elegant history is on full display in the lobby, a preserved masterwork of architecture and taste restored thanks to a $170 million renovation. Built only a bit after in 1895, The Alise Chicago, Staypineapple, was one of the first skyscrapers in the city at 14 feet. It has fully modernized rooms, but the stairwell and outside façade tell the clear story of a building with tremendous history and deep roots in the city.

These historic hotels are generally downtown, near the action and historic center of commerce and industry. While they may vary in terms of how much they’ve preserved their historic look and feel, they are all devoted to comfort and cleanliness. Expect to spend a little more on a stay in a historic hotel rather than a more modern, low star hotel. If you’re a fan of architecture, a by-gone era of opulence and service, and the finer things in life, you’ll appreciate making one of these locales your base of operations during your Chicago trip.

The Langham Hotel Chicago

The Langham Chicago is a five-star hotel situated along the Chicago River next to Magnificent Mile. There are a lot of on-site perks, including a spa with aromatherapy showers, a spacious indoor pool, a kid’s playroom, and a movie theater that can comfortable seat 12.

InterContinental Chicago Magnificent Mile

Located in the trendy River North district on Michigan Avenue, InterContinental Chicago Magnificent Mile is a blast from the past. The historic 1929 building features many of its jazz-era original features, including an olympic-sized swimming pool. There’s also a spa, fitness center, and Michael Jordan’s Steakhouse.

Viceroy Hotel Chicago

Viceroy is a five-star hotel in the heart of Chicago’s Gold Coast neighborhood. In the former home of the 1920s era Cedar Hotel, Viceroy today offers unadulterated luxury in the form of Michilin Star dining, a rooftop pool and lounge, and an on-site Tesla to take you around in style.

Waldorf Astoria Chicago

Waldorf Astoria Chicago is a five-star hotel in the heart of the swanky Gold Coast neighborhood. Of course, there are five-star amenities to match, like an on-site spa, lap pool, and fitness center as well as awarded restaurants, in-room wet bars and marble bathrooms with separate soaking tubs.

Warwick Allerton Hotel

The Warwick Allerton Chicago is situated on Magnificent Mile in one of the city’s most recognizable landmarks. The jazz-era building will take you to simpler times, with luxe amenities like an on-site lounge and in-room massage services. There are plenty of modern perks too, like new HD televisions and iHome docking stations.

Millennium Knickerbocker Chicago

Built in 1927, today’s Millennium Knickerbocker Chicago pays homage to another time. The original Crystal Ballroom is just as dazzling as nearly a century ago, and you can drink like Don Draper in the Martini Bar. At the end of the day, rest in your bed and binge on your smart TV.

The Drake, a Hilton Hotel

Along the shores of Lake Michigan’s Gold Coast sits The Drake, a Hilton Hotel. The iconic Chicago Institution has been open for nearly a century. Its on-site bar was the first to serve alcohol after the repeal of prohibition. So grab a cocktail and party like it’s 1929.

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Situated on the Chicago River, Hampton Inn Chicago Downtown N Loop/Michigan Ave has premier real estate in downtown Chicago. Part of Hampton hotels, this location comes with all the standard perks: free WiFi, complimentary breakfast, 24-hour business and fitness centers and a satisfaction guarantee.

River Hotel

River Hotel gets its name from its impressive location on the south bank of the Chicago River. Stocked with the basic amenities, the three-star accommodations offer one of the best bargains around while providing walkable access to many Chicago attractions and the adjacent Theatre District.

Club Quarters Hotel, Wacker at Michigan

Club Quarters Hotel, Wacker at Michigan is situated in the former Mather Tower, Chicago’s most slender high rise. Tucked along the south bank of the Chicago River, high-tech accommodations offer access to lots of Windy City landmarks. You can check in and even open your door straight from your smartphone.

LondonHouse Chicago, Curio Collection by Hilton

A luxury lifestyle hotel along the Chicago River, LondonHouse Chicago, Curio Collection by Hilton is situated within the historic London Guarantee & Accident Building. Interiors pay homage to the heydey of Chicago while incorporating modern furnishings and high-tech extras, like smart TVs and free WiFi.

St. Jane Hotel Chicago

Situated in the historic Carbon and Carbide Building, the St. Jane hotel is one of the newest places to stay in Downtown Chicago. Just blocks from the Chicago River, the Art Deco building is equally stunning inside. For the most luxurious experience, reserve a room in The Tower on floors 24 and up.

W Chicago City Center

A rare Beaux Arts building in downtown Chicago is home to the W City Center. This Marriott-affiliated hotel offers a cozy respite from the buzz of its popular neighborhood. Both the on-site bar and restaurant, Midland Social Club, and guest rooms alike pay homage to the city’s history with unique decor.

Hilton Chicago-Michigan Ave Cultural Mile

Hilton Chicago is situated on Michigan Ave across from Grant Park. The picturesque location is walkable to Museum Campus and Soldier Field. The hotel itself has some top-notch amenities, like a large indoor pool and several on-site restaurants. Take advantage of the swanky fitness center and Peloton bikes.

Palmer House A Hilton Hotel

Potter Palmer built Palmer House for his wife Bertha in the 19th century. Open since 1873, it is the longest continuously operating hotel in the U.S. Guests today can sleep in the historic accommodations just a stone’s throw from Millennium Park and the Art Institute.

Silversmith Hotel Chicago Downtown

A stone’s throw from Millennium Park and the Art Institute of Chicago, the Silversmith Hotel boasts an unbeatable location. That, coupled with a sophisticated design, trendy on-site restaurant, ample business services and complimentary WiFi make it worth the price.

Chicago Athletic Association

Stay in the lap of luxury like the elite members of Chicago’s Gilded Era at the Chicago Athletic Association Hotel, tucked alongside Millennium Park. Once a members-only retreat for the rich and famous, today the classic architecture, on-site eateries and unparalleled service is open to all.

Staypineapple The Loop Chicago

Staypineapple, An Iconic Hotel, The Loop Chicago is tucked in a historic building near the bustling theater district. Its trendy location and modern amenities are anything but staid, offering bright robes and matching yellow beach cruisers for guests. Plus, you can bring your pup!

Kimpton Hotel Allegro

Adjacent to the Cadillac Theatre, find the Kimpton Hotel Allegro and its storied architecture. Equally luxe interiors are outfitted in Mid-Century Modern design that complements the classic cocktails served in the upscale lobby bar. The four-star accommodations offer a lot for the price: primarily, a location walkable to the best Windy City arts and entertainment.

Virgin Hotels Chicago

Tucked in Chicago’s business district just south of the Riverwalk, Virgin Hotels Chicago believes in work hard, play hard. Amenities offer equal amounts of business perks with after-hours entertainment at its swanky bar and rooftop club. Plus, you can book a room specially catered to your pup.

The Blackstone, Autograph Collection

Want to sleep in the same hotel as 12 U.S. presidents and Chicago’s most notorious gangsters? The Blackstone, Autograph Collection, has been restored its Prohibition-era glory. Throughout, find historical artifacts and period-styled guest rooms, that are of course complete with all of the amenities for modern luxury.

Hotel Blake Chicago

Hotel Blake has it all: a historic 19th-century building and contemporary cachet. On historic printers row, enjoy a location within walking distance of Grant Park and The Art Institute. There are also free perks, like free WiFi, on-site dining and a 24-hour gym.

Central Loop Hotel, Chicago

For thoroughly modern travelers, there is no better than the Central Loop Hotel. Its central location is a given, but the futuristic perks are unexpected: mobile check-in, in-room sleep systems and the “fastest WiFi in Chicago.” Plus, this is one of the area’s more affordable options.

Kimpton Gray Hotel Chicago

The Kimpton Gray Hotel is a shiny new penny in Chicago. Its rooftop bar and fine dining establishments are the talk of the town, much like the gym’s on-trend Peloton bike. The Gray also lets you bring Fido for free, who you can take for a walk in nearby Millennium Park.

Hampton Inn Majestic Chicago Theater District

The Hampton Inn Majestic Chicago Theater District boasts prime real estate next to Hamilton in the heart of downtown. Perks include a free hot breakfast, a 24-hour gym and complimentary WiFi. Additional amenities for families make this a great option for groups.