I've said this a million times but after watching at least 3 different people have their umbrellas flip out on them (literally) during yesterdays monsoon while I sauntered along just fine I feel like I have to share the secret to my dry + problem-free success: Gap makes the cutest, affordable + durable umbrellas around.
I've had two Gap umbrellas over the past 6 years or so + if they can last that long in the Windy City they must be pretty damn good. The only reason I had to buy a new one recently was because my hand (with said umbrella clenched in it) was trying to stop a CTA door from closing + my only options were to drop the umbrella + slip my hand out or get pulled to my death by a moving train. I was pretty sad to see if go but I knew exactly where to get a new one.
There doesn't seem to be any on their website, but you should be able to find a couple cute options in the store for $30 or so. It's totally worth the special trip/few extra dollars.