Hi! Well, I am not living the condo life anymore but I was up until my daughter was 18 months so I am happy to share my experiences and opinions. We were living in the South Loop right on Michigan Ave, and it was a fabulous location - we loved it! And still miss it to some extent. However, what I have found is that while condo life can be doable, it is definitely a short-term option with children.
In our case, we had only a 2 bedroom/2 bath with 1 balcony, so we felt cramped for space as soon as my daughter started walking. For you, having the extra bedroom and family room will give your child a play area (which you will find you'll need more and more as your daughter gets older) so that helps. However, once you add to your brood, I think you'll find that you miss your house and yard. There was a young family who lived in our building - they actually lived next door to us. They had 3 kids, oldest was about 8, and lived in a 3 bedroom with a family room as well. I will tell you that those kids were ALWAYS playing in the hallway. Having a child myself, I was a bit more understanding, but having a soccer ball kicked against your door every afternoon gets to be a bit annoying. Many times we would see them riding bikes or playing hockey in the building's garage. Not only was this frustrating as a driver, but it is so unsafe! Often, they could also be found running around the lobby chasing each other. It was aggrevating but honestly, where else were they supposed to go? I can remember thinking to myself, I wish these people would move and buy their children a house that they could play in! I felt terrible for them that they were confined to a condo building.
Honestly, this is one of the main reasons we decided to move -not because they were a bother, but because we saw how important it is for kids to have space to play. It was like seeing the future. It was harder to realize it when our daughter was just an infant, but the older she got the more we could tell - she needed a home. Even with parks just a few blocks away and a pool in your building, we have a lot of bad weather in Chicago. Not just winter days, but rainy spring and summer days too. Let's not forget, you need to escort your child to go and play in a park - something you won't really choose to do when the weather is not great (even if you think you will). And let's face it, you won't want to go as often as they'll want to! We now have a 4 bedroom house with a full finished basement and a yard - I can send my daughter (now over 2 years old) outside to play in the back while I watch her from the kitchen as I do dishes. Rainy days are no problem - she has a full play area in the basement. And when it snows, we can play outside in it but then come back in right away as soon as we are done - no need to walk to and fro, which can be no fun in the snow.
All this being said, I completely understand your desire to eliminate your commute. My husband's job is downtown - moving to the burbs would mean a long commute and less time with our family. For this reason, we chose the Bridgeport neighborhood for our home. So now, I am just going to throw this out there incase you have not considered the area already. This is none of my business, I know, but I just came from the neighborhood you're considering and I know what the condos there are going for, especially the size and location you are considering. You could get a FANTASTIC house in Bridgeport for that money and still eliminate your commuting issue. We are literally 6 minutes from our old condo. We still have easy access to everything downtown. We are close to public transportation. And just a quick 4 minute drive to the lakefront. I go to the same supermarket, salon, and doctors' offices. True, these things are not at our doorstep like they once were, but that is life with a child - we had to make some of those sacrifices, but honestly not that many. We still have most of the amenities we love about the city. It was a win-win for all of us.
I know Bridgeport does not have a glamourous reputation - we are yuppies who were a bit turned off by it's blue collar-ness, if you will. But there are so many young families like ours moving here it is unbelievable. The houses that are being built here would astonish you. And Bridgeport is slated to be the next big development area after the South Loop. This is where developers are coming now that the SL market has become saturated. Main street retail areas are planned for major renovations and there are a number of tear-down/rebuilds being done on most blocks. We've been told that over the next 7-10 years, we can expect our home value to increase between 25-50% (if this housing market ever turns back around!!).
Anyway, I am not meaning for this to turn into a sales pitch for Bridgeport! I just wanted to give you some insight into our situation because I think it is very similar to yours. We were looking for many of the same things you are, and we found the answers here, right next door to the South Loop. Either way, I hope this will be helpful as you consider your all of your choices. The city has tons of great options, that's for sure. Whatever you decide, I wish you happy house hunting! : )