Happy Tails and Trails

A two-site operation west of the Loop, running daycare, overnight boarding, grooming and both private and group training.

Boarding requires daycare enrolment first. This is the single most important thing to know before you plan around it: the business does not take boarding-only bookings from dogs it has not already met through its daycare program. If you are looking for somewhere to board a dog for a trip next month, start the daycare process now, not the week before.

Two locations, and they are not interchangeable. The main site is on Walnut Street, with transport available to it. The second, at 1 W Superior Street in River North, takes dogs under 35 lbs only. Both are covered by this listing; confirm which one your dog would be at when you enquire, because the size rule decides it for you.

Also offered. Puppy socialisation classes, private and group training, and grooming and spa services.

Hours. Weekdays 7:00 AM to 7:00 PM, weekends 9:00 AM to 5:00 PM, closed on major holidays.

What is not published. Nightly rates, vaccination requirements and overnight staffing are not stated on the site.

Source: the business's own site, read 2026-09-25.