If you're in Chicago you're going to need more light to stand out from all the background light. I'm a big fan of having multiple lights, and the lights cycocommute are hard to beat for the money. If you put on of those on the handlebars and get a higher quality light for your helmet you'll have a backup and will probably find the benefits of the extra visibility that comes with a helmet light. I use an older version of one of these lights, on high on my helmet and the bar light on low at night. With both winter and more economic changes coming with the escalating trade wars it would be good to buy something sooner instead of later.