Need advice on a good year round commuter bike for Chicago

Hello!

I am fairly new to the cycling scene and want to buy a road bike that I can ride year round in the city. I am interested in buying a cyclocross. I've done a little research on winter biking including the pros and cons of internal gear hubs vs external gears, single speed vs multi speed and narrow tires vs thicker tires. I currently own a KHS Flite 900 Team Issues 25 mm tires on Campy vennto G3 wheels and campy group set. This bike was gifted to me and I'm well aware I don't fully appreciate it because I just don't fully understand bike parts - yet. I was told this is a racing bike and am not sure if I should use it as a year round commuter. If I buy a cyclocross what should I look for in regards to group sets frame (I want something light) and price. My price range is $300-$650 currently shopping Craigslist for potential bikes. Suggestions thoughts advice on what I should do is welcomed and incredibly appreciated.

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 The nice folks at The Recyclery, Working Bikes, or West Town Bikes should be able to help you get a solid commuter for a good price.

 And don't forget to add on some fenders in addition to a rack, crate, or panniers.

Do you use the current bike to race?

If not, then why bother buying another bike?
Just buy a new set of wheels specifically for commuting, add fenders and a rear rack, and replace the tri-bar.

What size tires would you recommend? I currently have a 25 on the back wheel and 22 or 23 on the front.

I have one bike which I use both for commuting and club rides on the weekend, and switch wheel sets for each purpose.  However, I have a steel frame bike which can handle carrying a fair amount of weight, and i do not have high end drive train components like you probably do on your KHS. 

For commuting you need a bike which can have a rack mounted and handle the weight put onto it.  Also you should get fenders to protect the bike from dirty, salty, gasoline infused water spray when you ride on wet roads.

I am concerned that a carbon fibre frame racing bike could hold up under the stress of carrying stuff on racks.  It is just not what it was made for.

If you do decide to only get new wheels, then get the biggest ones which will fit along with a fender.  My commuter wheels have 40mm tires, and I *rarely* get flats.  When i rode on my 26mm Compass tires I frequently got flats.

Honestly, even for racing and fast club rides, many people are switching over to 25mm tires.  As your 23mm tire wears out, I'd recommend considering just replacing it with a 25.

That said, just from the small profile pic, I'd bet you'll have issues getting anything larger than a 28mm tire on your current setup (if that size even) given the bike's fork and seat-stay clearance, and even then you very likely won't have room for full fenders.   It would be worth talking to a local bike shop about what will fit. 

For commuting, I personally wouldn't run anything smaller than 28mm, and I think something around 32mm (which is what I ride) or above would be even better. 

Honestly, if you have the room and funds, I'd recommend keeping the nice bike set up for long rides on 25mm tires, and grab a solid commuter bike that you can ride with larger tires (32mm or above), a rear rack, and fenders.  You could potentially spend so much in converting your current bike (new handlebar, new shiffters, new wheelset, etc.) that it likely would come out i the wash anyway.  I'm admittedly a big fan of having multiple bikes rather than trying to get one bike to do everything, however.    

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