Welcome to Cleveland
I don't run into many people relocating to Cleveland -- usually relocating *from* from Cleveland. Aside from economic/employment opportunity, Cleveland is a much nicer place to live than most people (non-residents) think.
Though born and raised here, I also have one foot out the door. As soon as the house is sold, maybe sooner, I am taking my third child and leaving for the far West to meet up with the rest of the family.
Have been to Chicago a couple of times -- liked it very much.
Since you are relatively new to cycling, here is the best tip I can give you. Look up the Ohio City Bike Co-op. For a nominal fee which includes membership, you can take a series of four bike repair classes (designed for beginners) that will save you a lot of money in bike repairs/adjustments you will learn to do yourself (not to mention the confidence boost). There are also members around all the time who will be glad to help you. A membership here is waaay worth it. I think it's still $80 for classes and membership, $40 for membership alone. It is located in The Flats, so if you're in an outlying suburb, maybe the drive is prohibitive.
Here is the liink to their website:
Talk to Jim or Pete. They will have the details on all the great work they do if you're interested.
Again, welcome to Cleveland. I'd be happy to answer any questions. I'm guessing you'll like it here.