I went to Chicago a year ago to see Drive-By Truckers. It was my first time there. It was a lovely city, and the trains were fairly easy to understand. Local eye-candy didn’t hurt, either, and there are plenty of Starbucks. But I was going there sort of on the cheap, and the hotel room I stayed in was … well, it was a dystopian little hellhole
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One of the (many) big differences between Disneyland and Walt Disney World for me is for Disneyland, I really prefer to just stay at one of the (not so) cheapo motels across the street. I've stayed at Disneyland Hotel several times and while an enjoyable place to stay, it just doesn't add that much to the experience for me (I would love to stay at the Grand Californian once though). However, I can't imagine not staying at one of the on-site motels at WDW. It changes the whole experience dramatically for me. I stayed at the Euro-Disneyland Hotel in Paris the time I went there... that was pretty freaking awesome I have to admit.
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