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I've never been to New York but Chicago is one of my favorite cities.
O'Hare is always a huge pain in the ass though. They always overbook incoming flights so there's usually a congestion problem, meaning delays. It happened to me just 3 days ago and happens every time I fly through there.
In Chicago I always like going to Wrigley Field. Something about that place is just awesome. Such a great vibe.
Boat rides on Lake Michigan are fun, would probably feel great on a hot day.
The science Museum and Shedd Aquarium are pretty cool. The Aquarium is the biggest in the United States I believe.
Brookfield Zoo is great, IMO. I like it better then the famed San Diego zoo.
The Navy Pier may interest you. The Sears Tower.
I haven't been there since I turned 21, so I really don't know what else is worth checking out.
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