There's definitely a chance of severe weather like this past weekend (heck in 2004 there was even a freak end of May blizzard) but the chances are slim. CLE is a great connecting airport and CO is usually generous with its reacommodations in the event of weather. Go for it and enjoy CO.

Keep in mind, Commutair's Dash-8's fly both routes. Lots of people here will moan about getting stuck on one, but I think they're fun little planes.