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South metro Chicago car rental location by public transportation

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We want to fly into Chicago, take the train into the city from the airport for a couple days visit, and then take some sort of public transportation (train maybe?) to a southerly location where we can pick up a rental car. We want a southerly car pickup location because we need to drive down a couple hours into Indiana for a day. Then, we want to reverse the process and drive back up to the southern Chicago metro area, drop off the rental car and then take some sort of public transportation to the airport. We can use either Midway or O'Hare as an airport.

Is this idea even feasible? I'd be okay with the idea of an airport rental, but my husband dosn't want to get tied up in Chicago traffic, and that is why we thought maybe we could get to the southern outskirts by train before picking up a rental car. Or, if we did just do the airport rental location, how long would it take to drive from either Midway or O'Hare to northern Indiana if it were rush hour? We'll be taking 65 into Indiana. Thanks.

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