It sounds like a pretty severe infection at this point. I'd go to the vet. You don't want him to end up with kidney problems, IVs and all that stuff.
Cranberry juice or tablets may help but that's more of a preventive than a cure. What's he eating? Even if it's good stuff it might not be right for him and could be causing problems. Look at everything he eats, not just his main food.
None of my guys have had UTDs so I don't have much to offer.
As to your allergies, are you taking antihistamines every day? That's probably a must for you and whatever you're taking may not be strong enough for the situation. If the doc didn't prescribe one for you, you may need to go that route. You may occasionally need a decongestant as well. You can still get Psuedophedrine HCL but you have to get it from the druggist They keep it behind the counter and you have to show id and sign for it but no script is needed. Walgreens has a house brand that's way less expensive. I use their Wal-phed which is a combo antihistemine / decongestant that works well for me. Don't bother with the decongestant sold in the isles. It's not wort the box it's packaged in if you have strong allergies.
I just looked at your profile. If you're still feeding Royal Canine, it's time to switch to a grain free. The worst reaction I've ever seen to a dog food was to Royal Canine Bulldog. there are many better rated brands out there with similar prices to RC. You can look at the lists on this board and then go to either the manufacturer's page or your preferred pet store's page and read what's in them and compare.