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I called them, they said their website is a 'Mis-print' and it's actually $40 a day. Thanks though!!
1) Any chance your family can bring their own bikes with them? That would solve most of the problem.
2) Have you checked in with the usual suspects: Working Bikes, the Recyclery, etc.? You may be able to buy four bikes cheaper than a $40/day/bike rental, and after your family leaves you could either keep them as "spare bikes" for other occasions or just redonate them back to where they came from.
3) Do you have a Plan B? Your family might not want to bike if it's pouring rain. If they aren't hardcore urban cyclistas, and haven't biked in years, it may just turn out that four or five miles may be their upper limit. Four all-day CTA passes and a well-planned route--heck, you could go on every single L line plus a whole bunch of bus rides for just a few bucks, getting off to walk Hyde Park, Andersonville, Roscoe Village, wherever, and your family may appreciate the ease of travelling by CTA more than they'd be able to sightsee while watching for potholes and trying not to get doored. Not to rain on your parade. It's really nice you'd like your family to see the city just as you do. Just an alternative cheaper strategy.
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