Earliest Baggage Checking Time

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You can check baggage at any station that offers checked baggage service up to 24 hours prior to departure. However, at Chicago if you have a roomette or bedroom, you can use the metropolitan lounge which has a day check luggage room.
 
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As Dave said, day check your bags with the Red Cap inside the Metro Lounge, they will let you know when to return to claim them before boarding time! A tip is customary, usually $2-$3!

If you want a ride on a cart to the platform with a Red Cap,and help with your bags boarding the train, let the desk person in the Lounge know, the staff led walk from the Lounge to your train can be long!
 
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