Chicago’s beautiful skyline continues to climb and its intrigue stretches outward, with new neighborhoods growing in popularity among travelers and new developments catching the eye of new generations of travelers. However, beyond all this new, new, new, there are historic aspects of the city that remain unchanged yet still just as luxurious and lovely as a seasoned traveler might expect. From historic landmarks to breathtaking architecture to timeless Chicago traditions, it’s easy to combine the newness of the city with its treasured past when planning any travel itinerary.
Chicago blends new and old effortlessly
One of the best ways to get a glimpse of Chicago history? A stay at one of the city’s many beautiful historic hotels. Here are seven to consider for your next trip to the Windy City.
Ambassador Chicago
Developed in the Gold Coast neighborhood in 1926, Ambassador Chicago is iconic, a boutique hotel with all the classic nostalgia and prestige one could desire. The property’s history is rooted in Chicago’s Jazz Age and was a destination for celebrities and politicians. Today, visitors enjoy beautiful views of Lake Michigan and easy access to Michigan Avenue, across all 285 guestrooms.
Just this year, the hotel introduced its J’Adore Ambassador Tour, which encompasses five initiatives that bring the Ambassador Chicago spirit to guests and locals alike in new ways, from pop-up art galleries hosted at the hotel to community holiday celebrations.
1301 North State Parkway
The Blackstone
The Blackstone takes luxury to a new level (Photo: Marriott International, Inc.)
The Blackstone is an exclusive, culturally- and historically-rich property, a Beaux-Arts hotel known for its luxury experiences. Stay in the Smoke-Filled Suite and receive access to the hotel’s members-only smoking lounge. Explore The English Room, with its stained glass, mahogany walls and ornate ceiling imported from an 18th-century English manor and then reconstructed at the hotel in 1908. Don’t miss the Art Hall; with 1,600 art pieces, it’s a museum all on its own, with its own curator. Lastly, make sure to book a stay in the Suite of Presidents, which has hosted 12 U.S. Presidents over the decades.
636 S. Michigan Avenue
Palmer House
The lobby at the Palmer House sets the stage for a truly unforgettable guest experience (Photo: © 2019 Hilton)
Palmer House originally opened in 1871 as a wedding gift and immediately gained status as one of the most luxurious hotels in the country. Unfortunately, less than two weeks after its grand opening, the hotel was utterly destroyed in the Great Chicago Fire. However, the Palmer House was rebuilt bigger and better than ever, making its second debut in 1873. It is now the country’s longest continually operating house. The huge property offers more than 1,500 guestrooms and suites, several dining options and a can’t-miss historic setting. This year, it begins significant restorations to its beautiful lobby, including the ceiling created from 21 Grecian frescoes.
17 East Monroe Street
The Drake
The Drake offers a wonderful Chicago location, but that’s hardly the hotel’s best feature (Photo: © 2019 Hilton)
The Drake first opened its doors in 1920 in the Gold Coast neighborhood. The property boasts a great location near Lake Michigan and Magnificent Mile, but its history is more intriguing than the locale. The hotel has hosted iconic celebrities throughout its life, including Bing Crosby, Marilyn Monroe and Charles Lindbergh. It frequently receives accolades for its continuous luxury, across it more than 500 guestrooms.
140 East Walton Place
InterContinental Chicago
Though the InterContinental Chicago on Michigan Avenue isn’t historic in of itself, the structure certainly is. The hotel’s south tower was once the Medinah Athletic Club, built in 1929. The beautiful historic space sports history inside and out. While the hotel’s remodels have brought it up to 21st-century travel standards, you can still get a glimpse of the interior that once was, when you visit the huge indoor swimming pool.
505 North Michigan Avenue
Chicago Athletic Association
This hotel also doesn’t boast a huge history as an actual hotel, opening as a boutique property in 2015, but the building dates to 1890, when it was an all-men’s club. Now, it’s one of the best places in the city to see and be seen, with its hipster atmosphere ensuring that the out-of-the-know travelers stay away and the truly hip make it to the rooftop party space after dark. With views of Millennium Park, a Shake Shack right inside and a coffee shop-turned-speakeasy, you can’t go wrong.
12 South Michigan Avenue
Staypineapple The Loop Chicago
This property was originally Hotel Burnham and was constructed in 1890. Now, Staypineapple Chicago takes on a new name after being known as The Alise Chicago through recent history. It wears its past with pride. The beautiful craftsmanship can be seen throughout and you’ll swear that they just don’t make hotels like this anymore. From the elevator to the cafe, everything is tip-top vintage, hearkening back to a golden age of high-end, luxury hotels.
1 West Washington Street
By Holly Riddle