Mike Egner's "Vintage Pennant Price Guide" pictures both and dates the Bears pennant to the 1940's and the Cubs pennant to the 1950's.
I believe Mike has said he has an update for the guide in the works which ads a great many pennants absent from the first one, but I would still recommend picking it up in the meantime. It has a simple, straightforward layout: pennants are arranged by team and each one pictured (b/w photo) with date (or date range), size, rarity, and value range given for each. Pretty quick and easy to look up most any baseball or football pennant you run across just by flipping to the team and scanning through the photos.
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