My Chicagoan friends tell me that this dog walking and cat care company is the city's best! With loyal and dedicated clientele and personnel, local doggies and kitties get to walk and play with animal lovers while their animal-loving people are busy. Chicago Urban Tails has two lengths of visits and walks (25 or 50 minutes), and even offers a tracking system to monitor exact times of exit and entry at your request. They only service one household at a time so your pets never have to worry about sharing affections, and they leave detailed notes afterwards of their stay with you.
However, my favorite perk is their Personal Concierge ($15 for 30 minutes). Unfortunately, pets in town are not allowed on mass transit so getting your big pals around can be difficult at best – with this service, they'll help you pick up dog supplies, drop samples at your vet, and even help pick up dry cleaning or wait for special deliveries, too.