My wife and I are thinking about heading down to Chicago from Milwaukee and would like some input into where to slip for the night. Should we try going up the river being a newbie to the Chicago waters? We would like to head out into the city for a great dinner and some night life. Also any input on how long the trip would be if we are cruising at about 55-60. since this will be my first time with my boat on Lake Michigan any watch outs or other advise would be most welcome.

Take a look at the post below called "Info???" some good info there about going to Chicago.
I would say if you want to be close to alot of action in your boat slip then Diversey Harbor is your best bet. Its walking distance to alot of night life in the area right down Diversey ave. If you want to be more downtown in the city then Monroe or Dusable harbor would be the way to go. Dusable has docks and locked gates so geting on and off the boat is easier then Monroe that you need to get a ride from the boat shuttle to and from your boat.
Monroe/Dusable is almost right next to Navy Pier. And a little walking around you can get to a few nice places in the area as well. All realy depends on what you have in mind to do or see.
Ging into the rive is a snap...just pay attention to what everyone else is doing in the locks...you'll figure it out easy enough. It can look intimidating the first time through but its no big deal........just DONT tie the ropes on the side walls to your cleats!!!!!
Going down the river is cool if you have never been or seen the city from the river....gives you a whole new look at things Other then that theres not much else to do on the river.

I'd say it will take you about an hour and a half +/-15min to get down depending on how the water kicks up.....about the only thing to watch out for on the way down from Milwaukee is if your gonna be following the showeline close.......around Racine theres a lighthouse just to the north that has some HUGE boulders under the water so if you stay a good 1/4-1/2 mile off you should have no problems and then again at the entrance to Racine its self theres a very shallow area betwen the entrance and the small lighthouse/marker island thats out in the water. Just stay to the outside of that and you should have no problems. I think if you have GPS coord. then you just mae a bee-line for the city and avoid it all God luck, have fun and ask any questions you want....we are here to help