O'Hare Airport
#2
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I'm not sure it's the fastest but there is a shuttle bus service right by baggage claim that will take you to most major hotels. The quickness will depend on how many stops it has to make before your hotel. You can also take the rapid rail system-there is a site where you can put in where you want to go and it will tell you which stop to use or where to transfer. Sorry but I can't remember how I found it, but I'm sure if you do a search for Chicago you can find it.
#3
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You're in luck. The fastest way is also the least expensive. Take the Blue Line 'el' train. $1.50 a person, about 40 minutes. You can change to the red line downtown to go north and walk three blocks over on Chicago Ave. or take a cab from a blue line station, probably Washington. E-mail me if you need any other info on Chicago.
#5
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Kelly-I've done this run many times. I would take the L during the day if I had no luggage. The airport vans run to nearly all of the downtown hotels and are much more convenient, i.e. they'll drop you right at the door. You can buy a one way or round trip ticket as well as reserving a pick up time. I believe the round trip cost is about $25 per person. I think a cab would be closer to $30 each way.
Enjoy the Westin. A nice hotel in a good location.
Enjoy the Westin. A nice hotel in a good location.