While in Chicago my sister kindly went to the effort to borrow a bicycle for me to tool around the city. It’s a beaut, with leather handles and seat and nice wheel guards. But we both have gotten to the point of hating it, mainly because it keeps getting flat tires in the REAR wheel. The wheel that has internal gear, making it almost impossible for us to take the wheel off to fix flat tires. Instead, we just pop the tire off the rim, pull out the tube, and find the puncture, all with the tire and tube remaining around the axle. This is probably why it keeps getting flats, we aren’t getting the tube properly positioned in the tire, causing it to be crimped, causing more flats.
It is a really cruisy bike though, which I like. I’m not a fan of road bikes where you are hunched over the handlebars, feeling like I could be thrown off headfirst at any point. The 3 gears have been pretty ok in Chicago too, since it is flat as a pancake here.
I’m still ready to get my utilitarian (with fancy wicker baskets) bike back that has puncture-resistant tires and not so wide handlebars. those wide handlebars wear my arms out!

I haven’t been here, but apparently you can get decent used bikes here for cheap:
http://workingbikes.org/sales
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