Take the Orange Line from Midway to Clark and Lake. Transfer to the Blue Line and take it to O'hare. It'll cost you $2.25 and take about an hour and a half. Taking a bus or taxi will usually take just as much time due to traffic.
It's Coach USA. They do hourly service between each airport. The cost is $24 which is kinda pricy in my opinion for such a short trip. Each trip requires a transfer though, so I bet taking the train is about the same time.
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