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One of great things about Chicago is all of the architectural surprises, like the JW Marriott. I’ve passed the J-dub a dozen times, but I never expected the grandeur that I found in the hotel, which was originally built as the Continental and Commercial National Bank in 1914 by Daniel Burnham. With grand staircases on each side of the block-long lobby, thick, rectangular columns, and marble galore, I almost felt underdressed in my jeans when I visited. Located, appropriately enough, in the Financial District, you’ll spot a lot of suits here during the week and a more leisurely crowd on weekends. Rooms are well-appointed, with natural light and marble baths. With 600-plus units, you can sometimes find some great deals here.