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Union Station Chicago is ENORMOUS. Allow plenty of time to know where you are going and when you need to be there. Amtrak arrives and departs around the clock to and from every direction. If you travel with kids and lots of luggage, a taxi is your best bet for getting to your hotel and taxis to most downtown hotels can run anywhere from about $8 to $18, depending on the size of your party, distance to hotel and amount of luggage. The bus is a cheaper alternative after a weekend of cab fares. The 156 bus stops right in front of Union Station. Arrive at the station an hour before departure, and be at the gate 30 - 45 minutes early. Reserved seat does not mean assigned seat (and the Amtrak Hiawatha trains from Chicago to Milwaukee and back are unreserved seating), so board early if you want to sit with your companions. If you are travelling with kids, be at the gate when the attendant calls so you can board early (elderly, disabled, and small children can board first.... it is a long walk out the platform to the trains.)
First class (sleeper) passengers can use the Metropolitan Lounge. This is a free private waiting room at the far east end of the station just north of the main Amtrak lounge. Luggage can be stored for free and there are soft chairs and sofas for your use. There are a few large screen TVs. Coffee, soft drinks, and snacks are served free.
On the second floor of the station is a large food mall.
Another good place to wait for your train is the Great Hall, a large, open area with benches (seen in "My Best Friend's Wedding) to wait and electronic boards showing arrival/departure times. During busy evenings where people are waiting for several different trains at once, the Great Hall is often a less "cramped" place for a longer wait than the waiting rooms.
Amtrak trains are often dry, so it is a good idea to purchase some additional drinks/water to take on-board unless you are traveling First Class where there will be coffee, juice and water available. Two newsstands (one by the Great Hall) are good places to pick up last minute magazines/snacks to bring on-board.