If you want to go to the hip neighborhood, Logan Square would be your pick. Longman and Eagle is a great restaurant. Revolution Brewery pub and Whistler are the good watering spots there. (CTA Blue Line California or Logan Square)

Violet Hours at Wicker Park is one of the finest cocktail bar in my book. Lines are formed as soon as it opens at 6PM. Big Star, a nice taco/whiskey joint, is right across the street, is always crowded because of the food. (CTA Blue Line Damen)

The hottest dining and night life scene would be the Randolph street at West Loop, between Halsted and Ashland. Tons of great restaurants and bars.  

Alternatively, you can always go to Wrigley Field area for typical sports bar scene, or Magnificent mile area (Michigan ave) for the typical tourist scene. The Viagra triangle (Rush and State and Oak) is adjacent to the magnificent mile, you would find high end restaurants with older crowds there (hence the nickname)

What's your mood and what are you looking for

John Hancock 95th bar. You can see the whole city for the cost of a drink

Chicago tours

f you have time in your schedule check out :
Openhousechicago.org
Offering free tours of Chicago landmarks  
This weekend all over town.  Enjoy

If you want a laugh. Go to Old Town and sww a 2nd City show. Home of John Belushi, Chris Farley, Joan Rivers (WAIT A MINUTE) they're all dead. Acrually worth the effort but get tickets in advance, they sell out. Nice area to bar hop also.