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Well, yes it is, but given day (like cubs or sox game) public transportation could be congested, it's something to consider. You could probably get downtown, but in my opinion just see a few things, and not have a time to really enjoy it.

I'll be there May 28th, it doesn't look like there are any games that day. I definitely understand your point about not enjoying it, but I just don't want to sit at the airport for 7 hours either.

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That's plenty of time to go out and do something. You could jump on the blue line right out of O'Hare and it'll take you directly downtown. I'd allow for probably an hour and a half travel time on the way back though so you don't fuck yourself and miss the flight. Still though, you'd have 4+ hours to wander around the city. I'm not sure what time your layover is, but if it's in the afternoon, plenty of shit to do downtown. If it's at night, that limits your options a bit, as the loop tends to die around 6 PM.

Or, there are plenty of strip clubs nearby!

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O'Hare is the end of the line in that direction, so it doesn't really matter what train you get on to go downtown, but it'll either say "54/Cermak" or "Forest Park." The tracks split in two direction, but not until after you pass numerous downtown stops.

On the flip, there's only one train and all it says is "O'Hare." Ask any CTA worker or person on the street and they'll tell you. It's pretty obvious, though.

If you make it to the Reckless at the Damen stop, ask for me because I usually work on Wednesdays.

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