If you do decide to drive, use spothero to find parking rates. Depending on what you plan to do, parking in one of the Millenium Park garages might work best. Plan to drive in probably after 9:30 or so, afternoon rush hour will start by 4, or even earlier, so you may want to plan accordingly.

If you stay in Skokie or Evanston, use the combination of CTA yellow and red line trains to get downton. Do not drive your car into the city unless you budget $50 per day parking costs. Staying in a suburb to save $ is a false economy and means commuting to your vacation. Be sure the suburban hotel you chose has easy access to a train into,the city. OR don't bring a car at all and use your savings to get a nice hotel downtown

It's good to plan your days in advance. Certain destinations will be better driving, others work well with the Yellow/Red Line trains (and kids do love them).

In addition to the Dempster station, there is a second Skokie Yellow Line station at near Oakton and Skokie Blvd. Both have a good supply of inexpensive parking. One of the benefits of taking the train is that you can wander about and not have to backtrack to the car.

There is almost no way to avoid our heavy traffic. Best bet on a weekday is to leave around 10 AM and stay downtown until after the evening rush, around 7 PM. On weekends, you can leave earlier in the A.M.

And if you stay in skokie, pick a hotel near old orchard mall or the marriott in wilmette..... you might wanna also consider looking in evanston (check prices) as CTA and METRA trains are more accessible and do not require a drive to the train station.....

Thank you so much for all the helpful suggestions. Really appreciate!