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Those car seat sleeping bags are a must-have imo. Used ours for both our kids - you just throw them into their car seat in their jammies. Keep one blanket handy in case it's mighty cold (we live in SW Ontario, Canada).Unless you are going to be taking your baby hiking in the mountains, you'll never need one of those bunting suit things. They are bulky, hot, and make it difficult to fit them into carseats. Most people won't have their kids that young outside in the winter except for to and from a car. Here in VA, we just use blankets. We even bought one of those things that fit over carseats, but never use it. I do realize that Chicago in winter is literal hell on Earth so it is a bit different, but I wouldn't spend the money on something like that, you'll just end up regretting it and unable to unload it on craigslist a year from now.
Another thing we bought for our second kid was a DOUBLEWIDE diaper bag. First kid we had one of those regular sized ones, and that was okay. But we bought a bigass diaper bag for our new little one and it's waaaay more handy. It basically becomes your outside-the-house baby survival bag...filled with bottles, food, soothers, diapers, wipes, backup sleepers, bibs .... .. .. .. .. .
Edit: ... .. .. . blankets, washcloths, baby crackers, bowls, spoons ... .. .