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Mass transit vs motorcycling in downtown Chicago

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We are planning a trip to Ilinois and Wisconsin in mid May. We will be traveling by motorcycle and pulling a small trailer to carry our clothes and camping gear. We plan to camp most of the trip. We would like to spend a few days in Chicago in a hotel near the central loop district or mag mile area but are concerned about safety, cost, and availability of parking the bike and trailer in the City. We are considering taking the train from Milwaukee, which would mean backtracking to get home, or from a Metra station outside of Chicago. We were looking at the Manhattan station. I realize there will be cost and other issues to be considered by leaving the bike and trailer in another location. What are the pros and cons of this idea? Any advice or suggestions would be appreciated..

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