I take Amtrak enough but getting to the station via public transit is too time consuming, is it ok/wise to leave one's bike locked up around union station? Maybe this isn't even an issue but since I take my bike inside at home as well as at work I don't know. Downtown seems pretty dead on the weekends and I'm always hearing of bike thieves with angle grinders that steal just about anything. My bikes are fairly non-descript and seemingly not theft-worthy but so were my wife's two bikes that were also taken from near our apartment. Thanks!

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Train stations are a pretty popular spot for bike thefts. Ravenswood Brown Line and Ravenswood Metra stops, Clybourn Metra, Madison Metra, Ogilvie Station and Union Station are locations which seem to account for higher than average thefts as reported to the Chicago Stolen Bike Registry. When a bike is locked at one of these locations, the thieves can safely assume that they have roughly until 5:00 pm to steal that bike. "Dead on the weekend" makes it easier to steal the bike without being detected, though there are still frequent thefts of bikes on "busy streets in front of an open business." I'd be reluctant to lock my bike at one of these commuter stations, even if it meant locking up a few blocks away and walking. There are bike racks at some CTA stations in the Loop which are "behind the turnstiles." I haven't seen a bike show up on the registry from one of these locations, though it would require you to pay the CTA admission fee to lock your bike there.
I work at union station and I would never lock a bike up outside. Suck it up and take public transportation. I you lock it to any of the railings along the river or in the station It will be removed by the building. It is considered private property and they do have the right to cut your lock.
Thanks for the replies. This is all pretty much what I'd figured but was somewhat hopeful that I was being paranoid. This is also remarkably irritating. I get along just fine year-round with a bicycle. I like painted lanes but am just as comfortable without. I appreciate that CTA has options for bikes on busses and trains. I'm just amazed that instead of leaving 20 minutes before boarding a train I have to leave an hour and a half simply because the odds are against my bike being there (or at least being rideable) when I return 36-48 hours later. Talks of turning the old post office into a shopping mall are replete with demands for adequate (cheap) parking because it would be foolish to expect patrons if it's too inconvenient. This is really where I wish the city would put it's efforts, into working with businesses to integrate bikes into "normal"/routine parts of people's lives. If i'm not allowed to take my bike with me, secure bike parking is the next step. What would happen if every time someone parked their car overnight they could reasonably expect it to have smashed windows and slashed tires if it were not just stolen whole?
But then I suppose everyone here has their own pet peeve regarding cyclist marginalization in the city. Well, there's my soapbox.

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