Are there any legal Casinos in the area? I may be attending a wedding there with a gambling buddy of mine, and I (we) be curious. I hope the answer is "no", given my last losses in Vegas.
Harrah's in Joilet. About 45 minutes from the intersection of I-55 and I-94 (down by McCormick Place), and about 20-30 minutes from Naperville.
Even closer to Naperville... there's a boat in Aurora... right downtown. Don't know who owns it though.
Not what I'd call reasonable. There are also four "river" boats in Indiana on the lake. The closest one is just across the Indiana state line in Hammond and that is also the closest location to downtown. It's probably only about half as far as going to either Aurora or Joliet. There is also one in East Chicago and two in Gary.
Absolutely not by any stretch of the imagination. You could take a Metra train from Union Station in Chicago (right by Union Station) to Aurora. I'm not really sure how far that is from downtown Aurora and the casino, but it would be a reasonable cab ride from that point, I would think.
Sounds like a plethora of options, though best served by a rental car. I assume there are tables, and not just slots and video poker?
Yes table games and slots. The boats in gary and east chicago have free buses that pick people up from downtown ask at your hotel.
As a longtime gambler, stick with the boats in Indiana. They have the shuttles, and because there are so many in a small area, the competition means better odds and better games. Slots, video poker, blackjack, caribbean stud, let it ride, pai-gow poker are all available in Indiana.
Depending on what time you'd be boarding/departing, there are MEtra trains that run to both the Aurora and Elgin boats. Elgin is closest to me, and, since I don't gamble very often, I tend to stay away from there. The minimum bets at the tables are a bit high for me.
There are also buses that run shuttles to the various casinos. I that's true at least for the Indiana boats.
Reasonable cab ride? It's about a two minute walk Just head south on Broadway (on the east side of the river) and then walk about 150 feet west on New York.
Actually Joliet has 2 casinos. Harrah's in downtown Joliet and the Empress casino a little further west in Joliet. Both have easy access off expressways. Joliet is approximately 45 miles SW of downtown Chicago.