6 Best Historic Hotels in Chicago

When you think about Chicago architecture your mind usually goes to skyscrapers and Frank Lloyd Wright. Am I right? One of my favorite types of Chicago architecture are the many historic hotels that are around the city. They tend to be unassuming and until you actually walk through their doors you don't see the beauty. Here are my top picks when you're looking for a little history during your stay.

505 N. Michigan Avenue

Built in 1929 this hotel started out as the men's organization, the Medinah Athletic Club. The decor throughout the building is unique and sometimes unexpected. The Assyrian style friezes on the 8th floor took me by surprise when I was there for a conference. They were beautiful. One of the best parts about the hotel is they have an Ipod shuffle you can borrow to take a tour of the historic areas of the building. 

17 E. Monroe Street

This Loop stalwart has been dubbed the longest continuously operating hotel in North America. The first building was built by Potter Palmer for his new bride Bertha in 1871 but burned down not even two weeks later in the Great Chicago Fire. He rebuilt it bigger and better. The first time I went up the escalator into the lobby I almost cried it was so beautiful. 

636 S. Michigan Avenue

While all of the hotels on this list have interesting histories The Blackstone takes the cake when it comes to it's celebrity history. Since it's 1910 opening there have been a number of famous patrons. Al Capone would hold meetings during his hair cut in The Blackstone's barber shop. Multiple presidents from Harding to Kennedy stayed in the appropriately named Suite of Presidents. 

140 E Walton Place

This beaux-art hotel sits on it's throne at the very end of Michigan Ave. You walk into a lobby with sumptuous blue carpet and ornate details all around the room. The Drake and its Palm Court are known as one of if not the best place in the city for an afternoon tea. One thing you might not know is that The Drake was home to the first themed restaurant in the United State, the Cape Cod Room was everyone's favorite seafood place in the 1930s. The iconic sign you see as you head down Lake Shore Drive has been around since the 1940s. 

720 S Michigan Ave

Like it's neighbor The Blackstone the Hilton Chicago has a very presidential past. Since it's 1927 opening every single president has stayed there before leaving office. This gorgeous Beaux-Arts style hotel has been in scenes for a large number of movies including some of my favorites such as My Best Friend's Wedding and Home Alone: Lost in New York. 

1 W. Washington Street

While technically a newbie in name the Reliance Building that houses Staypineapple has been a Chicago institution since 1895. There were some big name architects for this project, John Root started the project and it was finished by Charles B. Atwood. It was one of the first skyscrapers in the Loop to offer amenities such as electricity and phones for it's tenants. Clearly Al Capone had a thing for Chicago hotels since his dentist was housed here. 

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