Dog Vacation Boarding
in Chicago, IL Near You
Planning a family getaway or finally taking that bucket-list trip? Your vacation shouldn’t come with a side of guilt about where your dog is staying.
At Happy Tails & Trails, our Dog Vacation Boarding Chicago experience is designed so you can actually relax—knowing your pup is safe, loved, and having their own little vacation while you’re away.
For 24 years, Chicago families have trusted us as their dog’s home away from home whenever they travel.
Why choose Happy Tails & Trails for dog vacation boarding in Chicago, IL
Happy Tails & Trails was founded in 2001 by Angelica “Angie” Iga, a former veterinary assistant who saw how stressful traditional kennels could be for both dogs and their humans. She envisioned something better:
A place where dogs are cared for like family and truly thrive physically and emotionally—even when their people are out of town.
Today, we’re:
- Family-owned and operated for 24 years
- BBB Accredited with an A+ rating
- Home to two fully equipped, climate-controlled facilities in Chicago
- Known for our philosophy:
“We’re more than just dog care providers — we’re your pet’s second family.”
When you choose our Vacation Dog Boarding Chicago services, your dog isn’t just being boarded; they’re staying somewhere they already know and love, with people who know them right back.
Vacation dog boarding in Chicago, IL for real Chicago travelers
Whether you’re catching an early flight out of O’Hare, heading to a beach for a week, or joining back-to-back conferences, our locations make dog boarding while on vacation Chicago simple and convenient.
We serve busy families and professionals from:
- West Loop & Fulton Market – close to our Walnut St. facility
- Streeterville & River North – near our Superior St. location
- South Loop & Lincoln Park – easy access to both sites
With two Chicago locations, pre-vacation drop-off and post-vacation pickup fit naturally into your travel days, not as extra stress on top of them.
Clients often tell us things like:
“I travel extensively for work and have said many times that I don’t know how I could have a dog if I didn’t have Angie.”
That’s the level of trust and peace of mind we aim for with every vacation stay.
Two dog vacation boarding options
for every Chicago, IL pup
Our Dog Vacation Boarding Chicago services are available exclusively to existing daycare clients. That means your dog already knows our staff, spaces, and daily flow before their first overnight. No “stranger kennel” vibes—just a familiar place with familiar faces.
We offer two vacation boarding options:
Facility dog vacation boarding in Chicago
At our 1613 W. Walnut St. location, dogs enjoy:
- Climate-controlled indoor spaces year-round
- Comfortable sleeping areas designed for longer stays
- Daily enrichment and group play with daycare friends
- Rest and recovery periods to avoid overstimulation
- 24/7 nighttime handler onsite so dogs are never left alone
Rates:
- $80/night for 1 dog
- $145/night for 2 dogs from the same household
This option is perfect for social dogs who love the routine of daycare and enjoy hanging out with their friends while you’re away.
“Boarding at Angie’s house” – premium vacation dog boarding in Chicago, IL
For dogs who would thrive in an even more home-style setting, we offer “Boarding at Angie’s house”:
- Located on a 3-acre private property—a mini countryside escape for city dogs
- Personalized, home-style care with plenty of supervised outdoor time
- Quiet, cozy sleeping arrangements ideal for seniors and sensitive pups
- Limited availability for a boutique, low-volume experience
Rate:
- $150/night
This is our premium vacation dog boarding option, often chosen for special trips, longer vacations, or dogs who need a softer, quieter environment.
Why dog boarding while on vacation Chicago feels different here
Extended stays come with their own challenges—and we’re set up for them.
Our Vacation Dog Boarding Chicago program is built around:
- Extended-stay expertise – we regularly host dogs for week-long and multi-week vacations
- Boarding exclusivity – only daycare dogs board here, so there’s no shock of a brand-new environment
- Routine continuity – same facility, same staff, same friends, similar schedule
- Daily socialization and exercise – no “all-day kennel” boredom
- Comfortable sleeping arrangements – climate-controlled, purpose-built spaces for rest
- Free bath with 4+ nights – your dog comes home clean and fresh after their stay
You can travel knowing your dog’s physical, emotional, and social needs are all being met—not just the bare minimum.
A day in the life of vacation dog boarding in Chicago, IL
During a vacation boarding stay, your dog’s day might look like:
- Morning: Breakfast, a bathroom break, and easing into group play with daycare friends
- Late morning/afternoon: Structured group play, enrichment games, and mental stimulation tailored to their age and temperament
- Midday: Rest and nap time in climate-controlled, calm spaces
- Afternoon: More play, enrichment, and one-on-one attention as needed
- Evening: Dinner, relaxing activities, and winding down for the night
- Overnight: Comfortable sleep with a 24/7 handler onsite, so someone is always there if a dog needs reassurance
Throughout your trip, you’ll receive photo updates and transparent communication, so you never have to wonder how your pup is doing.
If you’d like, you can also schedule grooming during their stay—and if they’re with us for 4+ nights, they’ll go home with a free bath.
Real Chicago, IL families, real vacation peace of mind
Our long-term clients use our Vacation Dog Boarding Chicago services year after year, for both business and leisure travel.
Dogs come home happy, settled, and pleasantly tired, not wired or shut down—and that makes the post-vacation transition easier for everyone.
How to book dog vacation boarding in Chicago, IL
Because we only board existing daycare clients, the first step is:
Once your dog is in daycare, booking dog boarding while on vacation Chicago is easy:
Customer Reviews
They take the best care of our Milli. She can be an anxious and shy dog but they've been so good to her over the years that she's really come out of her shell. Happy tails is very accommodating and easy to work with, I recommend them very …
Thank you so much for sharing this. Milli has come such a long way and we absolutely adore her. We’re grateful for your trust over the years and we’re so glad she feels safe and comfortable with us.
via 
Angela and the team are terrific! Max enjoys his days there and we find them to be very accommodating.
Thank you for the wonderful review. Max is a joy — gentle, social, and always happy to be here. We appreciate your trust and your recommendation.
via
My dog runs to the front door and can’t wait to get in. He really likes it there! Easy parking for pick up and drop off. Very friendly and accommodating staff. Highly recommended!
Thank you for the wonderful review. It means a lot to hear that your pup enjoys coming in and that our team has made things easy and welcoming for you. We appreciate you recommending us.
via
This place is like family to us. Tinkoo is so happy each time he comes here. His tail looks like it’s about to fall off from wagging anytime he sees Angie lol. You can tell she loves what she does and it shows
Thank you so much for this! Tinkoo is truly part of our Happy Tails family. His whole‑body wiggles always make our day, and we love seeing how excited he gets when he sees us. We appreciate you trusting us with him.
via
Louie had a great day at his new daycare! Everyone I came in contact with was very attentive and helpful. Based on my experience I would recommend their daycare services!
“Thank you so much for bringing Louie to spend the day with us! We’re thrilled to hear he had a great first visit. Our team loved having him, and we appreciate your kind words about their care and attentiveness. We look forward to seeing Louie again and being part of his daycare routine.”
via
I have been bringing my dog here since 2018, the staff has always been exceptional. They take care of my dog like she was one of theirs.
“Thank you so much for sharing this. Layla has been part of our family since 2018, and we adore every moment we get with her. She brings such a sweet energy to our days, and caring for her like one of our own has always come naturally to us.”
Angie
via
We are SO grateful for Happy Tails and Trails 2.0! Polee LOVES playing with his friends, and Brady & Luis are so good to him. He literally drags me there and is so excited to get there every day!!
"This absolutely makes our day! Polee is such a joy to have here, and we love seeing how excited he is to come play. Brady and Luis adore him, and it means so much to know he feels at home with us. Thank you for trusting Happy Tails & Trails 2.0 with your pup — we’re so grateful to be part of his daily happiness!"
via
Our dog had a great time, the employees were very helpful and caring for the dogs. Great value, service, and care
Thank you so much for your kind words! Sundance was absolutely wonderful—he had a great time playing and relaxing with the other pups, and was truly a pleasure to have with us. We’re so glad you felt supported by our team and appreciated the care we provide. Looking forward to seeing Sundance again soon for more tail-wagging fun!
Angie
via
Ready to plan your
dog’s vacation while you enjoy yours?
If you want your next trip to feel lighter—knowing your dog is safe, known, and genuinely cared for—our Dog Vacation Boarding Chicago services are here for you.
Next steps:
📞 Call: (312) 388-9077
📧 Email: happytails2@comcast.net
Go enjoy your vacation. We’ll take care of the tail-wagging part back home. 🐶✨
