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To stay here is to experience Chicago architectural history first-hand: the rehabbed Reliance Building is one of the world’s first skyscrapers, built in 1895. The 14-story landmark hotel was named for architect Daniel Burnham, and the first floor remains a throwback to the Gilded Age, with its bronze chandeliers, marble columns, fireplace, mosaic tiles, and restored elevator, complete with dramatic grill. The vintage thread continues to the gold and blue guest rooms, which are quite small, with just enough real estate to fit a bed, desk, and chaise (in fact, suites here are the size of many standard rooms at other properties). History buffs who don’t mind the squeeze will enjoy wandering the halls, where it’s still easy to visualize when this was a functioning office building and the place where Al Capone’s dentist worked. Visit the Atwood Cafe on the first floor for upscale comfort food, and stop by the lobby for hosted coffee in the morning and wine in the evening. The hotel also offers complimentary bike for guests to borrow.