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This will be my fourth year in a row going to the Derby. The short answer is that you probably have unrealistic expectations, especially at this late date.
1. Price/availability of Derby tickets: The infield is what, like $60 this year? If you are expecting to get a reserved seat, with a view of the racetrack, for less than $100? I think you are going to be disappointed. You might get amazingly lucky, but I doubt it.
2. Lodging: You are really late on this. I made my reservations in January. You'll have to stay out of town somewhere, although you can probably get closer than Lexington.
3. Renting a car and driving to the Derby itself: This is a really bad idea. You can't imagine the bedlam that you will find at Churchill on Derby day. There are a couple of venues around town that have parking and a shuttle (Papa John's stadium comes to mind) and that will definitely be your best bet.
It's a fun time, but it does require planning.
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