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Overwhelmed planning a trip to Chicago

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My wife and I along with our son who will be just over one year old will be traveling to Cleveland this August for the football hall of fame's induction weekend. I asked my wife if we could extend our vacation by then traveling to Chicago for a few days. She asked me to do some research before we commit to this. I was looking for a hotel in the city but I haven't been able to find a hotel for under $200 a night which would be way over budget. I started looking at some suburbs and found a reasonably priced hotel in Oakbrook Terrace about 20 miles out of the city. I'm getting nervous about doing this though because all I have read about the traffic getting in and out of the city as well as the high prices for parking around the city. I'm also quite overwhelmed about organizing what to do on what days while visiting. There seems like there is So much to do! Some things I would like to see/do include the zoo, aquarium, Willis tower, navy pier, children's museum, millennium park , cubs game, boat tour, field museum... (We would be in town 4/5 days.) We would pretty much just want to maximize our time in town.

Any help in getting my thoughts/plans organized would be appreciated so very much!

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