4. Get a room

"I would recommend staying in a hotel downtown. Any hotel. Just book a room. The last time I was in town, I stayed at the Hotel Indigo (1244 N. Dearborn), which is near all the clubs on Division, so it may be a better spot for someone who enjoys that scene. In one room, the walls may be floor-to-ceiling photos of blueberries. In another: a floor-to-ceiling photo of a cable-knit sweater. Odd but also oddly intriguing. But if you want to be closer to the theater district or the museums, stay in the Loop. The Palmer House [above] is definitely worth a look. Chicago is a city for walking, so base yourself in a hotel but get outside and walk around."
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