Our umbrella is the Chicco Liteway. It's ~$120 a BRU, folds small, light, canopy, reclines, has a small "basket" and a cupholder for parents. It doesn't have a tray though. It was great when DS was younger, but he likes his tray, so we only use for short trips now.
I'm currently looking at the BJ Micro on albeebaby.com on sale for $99. Has the tray option, but I'm not sure how "small" it folds. My DH might flip out if I buy another stroller. LOL. I'll be curious to see other responses.
We use a Jeep lightweight stroller. I bought it at Walmart for around $50. I was suprised at how easy it was to assemble and how sturdy it actually is for the price. It has a full reclining seat, nice shade, and a drink holder for mommy or daddy as well as an under the seat basket area.