Dog Walking
A Full Day of Outdoor Exploration, Enrichment, and Friendship
Dogs were made to move, sniff, explore, play, and experience the world around them. Adventure Days give dogs the opportunity to leave the city routine behind and spend several enriching hours outdoors with a familiar pack.
Small Packs and Personal Attention
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Experiences Built Around the Dogs
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Regular Photo and Video Updates
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Patient, Individualized Care
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Convenient Transportation
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Small Packs and Personal Attention • Experiences Built Around the Dogs • Regular Photo and Video Updates • Patient, Individualized Care • Convenient Transportation •
GIVE YOUR DOG A BIGGER DAY
What Is an Adventure Day?
Dogs were made to move, sniff, explore, play, and experience the world around them. Yet even well-loved city dogs can spend long stretches indoors and follow the same neighborhood route day after day. An Adventure Day gives your dog the chance to leave that routine behind and spend several hours exploring dog-friendly destinations throughout Chicagoland.
This is not a quick walk, a crowded daycare room, or a simple trip to the nearest dog park. It is a complete day designed around movement, curiosity, fresh air, appropriate social connection, and the natural behaviors that help dogs feel fulfilled. Depending on the weather, season, destination, and dogs attending, the pack may hike wooded trails, explore open prairie, splash at a beach, swim, run, investigate new scents, play together, or settle into a quieter walk and rest in the shade.
Every outing is planned around the actual dogs attending that day. Age, health, energy level, confidence, play style, friendships, and comfort in different environments all matter. The goal is not to exhaust dogs at any cost. The goal is to give each dog a safe, satisfying experience that leaves them physically exercised, mentally engaged, socially connected, and ready for a well-earned nap at home.
Why Choose Chicago Adventure Pack
ADVENTURE DAYS
Our signature service - much more than daycare—a full day outdoors. Dogs leave the city routine behind to hike, run, swim, sniff, socialize, and relax in nature with a familiar pack. Pickup and drop-off are included.
PERSONALIZED, SAFE DOG WALKS
Thirty, 60, and 90-minute walks tailored to your dog’s pace, routine, energy level, personality, and goals from stimulating sniff walks to substantial exercise.
Every walk is an adventure
STRUCTURED ENRICHING, SAFE OVERNIGHT CARE
Personalized care that maintains your dog’s familiar routine while providing tons of exercise, enrichment, companionship, walks, meals, medication when needed, and regular photo and video updates
Our Services
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30-minute walks
Give your dog more than another walk around the block. Chicago Adventure Pack provides all-day outdoor adventures, personalized dog walks, and thoughtful overnight care designed around your dog’s personality, energy level, and needs.
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60-minute walks
Give your dog more than another walk around the block. Chicago Adventure Pack provides all-day outdoor adventures, personalized dog walks, and thoughtful overnight care designed around your dog’s personality, energy level, and needs.
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90-minute walks
Give your dog more than another walk around the block. Chicago Adventure Pack provides all-day outdoor adventures, personalized dog walks, and thoughtful overnight care designed around your dog’s personality, energy level, and needs.
THE PACK LEADER
A Lifelong Dog Advocate and Trusted Adventure Leader
Jared Hocking is the founder of Chicago Adventure Pack. For more than 15 years, I have cared for dogs of different breeds, sizes, ages, personalities, and backgrounds.
My experience in animal rescue shaped the way I approach every dog—with patience, compassion, structure, and respect. I take time to understand each dog’s routines, favorite activities, fears, friendships, and unique quirks.
The Process Is Easy
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Meet & Greet
We will meet you and your dog to learn about their personality, routine, needs, and adventure goals.
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First Walk
A personalized introductory walk helps Jared build trust and understand your dog's pace, behavior, and communication style.
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Adventure Day
Your dog joins a thoughtfully matched pack for a full day of outdoor exploration, exercise, enrichment, and fun.
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Follow Up
Afterward, we will discuss how your dog did, share observations, and recommend the best plan for future adventures.
Loved by Chicago Dogs and Their People
Families trust Chicago Adventure Pack for dependable, personal care and meaningful outdoor experiences. Clients consistently tell us their dogs return home happy, fulfilled, and ready for a well-earned nap.
Frequently Asked Questions
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We offer All-Day Adventure Days, 30-, 60-, and 90-minute dog walks, puppy visits, enrichment visits, medication administration, and customized exercise plans. Recommendations are tailored to each dog’s age, energy, temperament, and routine.
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Use the contact form to tell us about your dog, their routine, temperament, energy level, and the support you need. Jared will follow up to confirm your service area, discuss fit, and plan the right first walk, visit, or Adventure Day.
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Adventure Days happen outdoors rather than in a crowded indoor facility. Dogs travel in a small, carefully matched pack for fresh air, movement, social time, sniffing, hiking, swimming, and exploration. Destinations and activities are selected around the weather and the dogs in attendance.
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Our primary service area includes Lincoln Park, Lakeview, Old Town, Gold Coast, River North, Streeterville, the Near North Side, and Downtown Chicago. Nearby neighborhoods may be available depending on routing and scheduling.
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Safety guides every decision. We evaluate weather daily, keep groups small, match dogs by temperament and play style, provide constant supervision, and transport dogs in a professionally equipped vehicle. Each dog receives individual attention throughout the day.
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Yes. You’ll receive regular photo and video updates so you can follow the adventure and see how your dog is spending their day.
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Dog Walks
30 minutes — $30
60 minutes — $40
90 minutes — $55
Adventure Days
Single Adventure Day — $60
10 Adventure Days — $550
Overnight Sitting
Standard night — $75
Each additional dog — $10 per night
Holiday night — $85
Each additional dog on holidays — $15 per night
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Yes. We offer discounts for dogs adopted from registered rescue organizations or shelters, as well as for clients who work in animal welfare or veterinary care. Please inquire about available discounts.
Proudly Serving Chicago Dogs
Chicago Adventure Pack primarily serves Lincoln Park, Lakeview, Old Town, Gold Coast, River North, Streeterville, the Near North Side, and select surrounding neighborhoods. Availability depends on the service, schedule, and pickup route.
ALL-DAY DOG ADVENTURES IN CHICAGO
Every Day Is an Adventure
Give your dog more than another walk around the block. Chicago Adventure Pack provides all-day outdoor adventures, personalized dog walks, and thoughtful overnight care designed around your dog’s personality, energy level, and needs.