QUOTE (RockRaines @ Oct 20, 2011 -> 05:17 PM)
So there are obviously parts of the city you need to see, and parts that are better left alone, especially if traveling during the weekend. For example, anything south of the Chicago River is pretty much worthless west of michigan. Therefor dont stay at the Palmer House or something crappy like that. Stay in River North of in the Viagra triangle. My picks would be the Conrad (Hilton) on Rush or something near there. If you want a river view there are alot of options, I would just make sure you are near Mich ave and preferably a little further north. The reason why is that the loop is completely dead at night and on the weekends. Like nothing going on at all. There is no need to go south of Wacker into the city unless you are going to take a ride up the Sears tower.
As for nightlife and food, you have come to the right place. There are a myriad of larger more popular and expensive places in the touristy area of River North and up into the Viagra Rush/Division area. The Triangle is very lively and is a must see if only to grab a drink somewhere like the Elysian Hotel. If you want to grab a lunch in Grant Park you can always check out the Park Grill, but I actually prefer going up north into Lincoln Park and checking out some the places there including the Uber Romantic North Pond $$$$
I'm sure if its nice you will be just walking around and will find something you really like anyway, but I can always give some particular suggestions. I prefer smaller intimate dining places in Chicago like Blue 13 or West Town Tavern, but you may want to be more mainstream and try out Topo or something of that nature and thats not a bad idea. If you continue up past division street you will start getting into the Old Town area near Wells streets which is a good walking neighborhood. On Division you have several old spots that were famous in movies like Mother's and Butch McGuires. Those are popular nightspots that have a ton of Chicago history. On North Ave there are still plenty of places and if you keep going north you get into LP and Lakeview which is extremely rich with places to check out.
Phew. SO probably cannot fit too much info into one post. If you DO stay in River North or Gold Coast area, I would recommend a few restaurants to check out:
Blue 13-One of my favs, its a little west on ontario, but small, intimate with a rock and roll attitude and fine dining
For steak dont miss Chicago Cut on the river.
The Purple Pig is a great spot off of Michigan
Chicago Q for BBQ
Big fan of Gilt bar for drinks as well as Public House for people watching
Graham Elliot for the slightly strange but famous chef experience
GT fish for atmosphere and seafood
Sunda for sushi
All the good italian places IMO arent located near there. I can give you some more info on that. If it looks like I have way too many suggestions its because I do. I eat out 3-5 nights a week and I am the go to guy for everyone I know to ask about places in particular areas. So once it gets closer I can help you narrow down choices. Sorry for the long post.
Great stuff, thanks!