parking at downtown is VERY EXPENSIVE

if you have a car, you may want to stay at outskirt areas and take public transportation to town. Chicago has excellent public transportation system. suggest you go to the city's public transportation site to check for the options.

Chicago is perfect for bidding hotels on Priceline as it has many areas you can do "free bid".

Be prepared to pay $30+ a day for parking if you stay in downtown area.

We have visited Chicago a few times as we like it very much in Summer time. The first time we had a car (no choice). We ditched our car at Rosemont Convention Center for 5 days and just took Blue Line to town every day. Subsequent visits we flew to Chicago and only took a rental car when we left Chicago going to Toronto and back.