My family and I go to Chicago at least once a year for either a long weekend or a week. We originally thought it would be a cheap alternative compared to WDW vacations but found that it could quickly cost as much if not more. It can be very expensive, especially staying downtown. What we do is stay out by O'Hare. There are a number of nice hotels, some with free parking, that are within a block of the CTA blue line and we can usually get a good rate of about $100-$150 a night. It is about a 30-40 minute train ride to downtown but my kids (age 2 and 8 when we started doing this) loved the train. The trains don't get you to Navy Pier so you have to switch to a bus but all felt safe and we had a lot of fun. The only time we were a little concerned was when we took the train to the museum of science and industry. You have to go through some more unsavory neighborhoods to get there. So if that is a destination for you, then I would drive to it.
If you plan on going to a lot of the museums downtown then look into the City Pass. It can save you a lot of money and is often a different line than walk up purchases and is typically shorter for entering the museum.
Staying out by O'Hare also puts you within 20 minutes of Woodfield mall where there is a Legoland Discovery Center and Rainforest Cafe (also a Rainforest Cafe downtown). If your kids are in to legos they would enjoy this option. It is not a whole day thing, just a couple of hours would suffice.
I would be happy to offer other suggestions as well just PM me. My wife and I used to live in the suburbs of Chicago and so we find ourselves back often visiting friends or taking our kids downtown.
Have Fun!
If you plan on going to a lot of the museums downtown then look into the City Pass. It can save you a lot of money and is often a different line than walk up purchases and is typically shorter for entering the museum.
Staying out by O'Hare also puts you within 20 minutes of Woodfield mall where there is a Legoland Discovery Center and Rainforest Cafe (also a Rainforest Cafe downtown). If your kids are in to legos they would enjoy this option. It is not a whole day thing, just a couple of hours would suffice.
I would be happy to offer other suggestions as well just PM me. My wife and I used to live in the suburbs of Chicago and so we find ourselves back often visiting friends or taking our kids downtown.
Have Fun!