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Use dog sitters vs daycare and it’s a lot more flex and comparable in price.
Pro
I dogsit occasionally, let me know if you need any help!
I’ve found most don’t have late pickup but if you are really planning to use it often, I would recommend building a relationship with the owner or manager and talking about your travel frequency and preferences. I’ve noticed that many places are single location / small business owners and so they make exceptions for repeat customers. We only board my dog for vacation since my wife is here when I travel but they have become more personal with my requests over the last few years and I can tell that people who use them for everyday daycare can do a lot more.
Tucker pups in west loop is great but hard to get in. They often have wait lists. I’ve also tried wag for walks and found a great walker.
Um, let me dog sit. My pup needs a friend.