I don't have much in the way of gym or hotel recommendations, but here are some restaurant recommendations.In and Around Boystown:
For great Italian, I'd go with Leona's http://www.leonas.com/
Also, in Boystown, Halsted's is pretty great. The BEST tater tots EVER! http://www.halstedschicago.com/
. They also have a video juke box there which is kind of fun.
If you're interested in deep dish pizza, I would highly recommend Giordano's http://www.giordanos.com/
for eating in (also has locations downtown) and Edwardo's Natural Pizza www.edwardos.com/
My favorite place for Mexican is Mayan Palace www.themayanpalace.com
. On Tuesdays and Thursdays they have half price pitchers, and the service and food there can't be beat! Many people might try to direct you towards Las Mananitas in boystown, but it's only good for margaritas- NOT FOR FOOD!
Good for any meal of the day, is Nookie's Tree http://www.nookiesrestaurants.net/
although I would recommend them for breakfast/brunch. If you go on a Sunday, be sure to get the cream of chicken and rice soup.
Although it's already been mentioned, GO TO ANN SATHER! You will not regret it!Downtown:
is my new favorite place to go on Michigan Avenue.
For sushi, I love Ra Sushi www.rasushi.com/
. Check out their happy hour specials!
I'm also a huge fan on Carmine's http://www.rosebudrestaurants.com/rest2.php
. I love the Ahi Tuna Salad there!
If you like Brazilian Steak Houses, I can't get enough of Brazzaz brazzaz.com
! TONS of food, but a little pricey.
If you just want some fancy drinks, you will love Martini Park www.martinipark.com/
. Tons of martinis to choose from and a great appetizer/food list as well. Also- although not located downtown or in boystown, if you like beer, you MUST visit Hopeleaf http://www.hopleaf.com/
, filled with tons of beer that taste great and many that you've probably never heard of before. They also have some food as well as a pretty nice wine list.
I noticed that Big Bowl and The Cheesecake Facotry were mentioned before. Truthfully, I wouldn't suggest Big Bowl- I think there are so many REAL asian restaurants here that you don't need some big corporations view on it. The Cheesecake Factory, although good, is a huge tourist destination, which is funny because they're EVERYWHERE in the country.
Hope the suggestions help! Happy eating!