A dog-friendly bar party, a morning 5K, a Ravenswood market and two Halloween parades: five plans for Chicago and nearby Lisle.
There’s more than one way to spend Halloween with a dog. Some will happily work a costume parade; others would rather keep moving and let the outfit stay home. For the next two weeks, Chicago and nearby Lisle offer both kinds of outing, with a bar party in Northalsted, a run or walk at Dan Ryan Woods, a dog-centered market in Ravenswood and two very different celebrations on Halloween morning. The trick is choosing the setting before choosing the costume. Here are five plans worth considering, with the costs, entry details and small practical catches that can make the difference between a good idea and a good day out.
Five quick picks
| Outing | Date | Area | Cost | Dog setup |
|---|---|---|---|---|
| Dog Day Saturday: Halloween Edition | Saturday, October 24 · 1–5 p.m.; costume activities around 3 p.m. | Northalsted, Chicago | No cover; humans 21+ with ID | Dogs invited; check event-specific dog rules |
| Howl-o-ween 5k – Dan Ryan Woods | Sunday, October 25 · 9 a.m. | Dan Ryan Woods, Chicago | $45 + processing through Oct 24 | Leashed pets welcome; no separate dog registration |
| 5th Annual Wag-O-Ween at Bosly’s Backyard | Sunday, October 25 · noon–4 p.m. | Ravenswood, Chicago | $15/person listed; checkout fees unconfirmed | Dogs welcome; event-specific rules need checking |
| 39th Annual Streeterville Dog Halloween Party | Saturday, October 31 · 9–11 a.m.; parade at 9:30 a.m. | Streeterville, Chicago | Free admission | Leashes required; bring a dog toy |
| Howl-o-Ween at The Morton Arboretum | Saturday, October 31 · 9 a.m.–noon; dogs may stay until sunset | Lisle | $7/dog ($6 member) + human admission | Dog ticket required; attended, leashed dogs only |
This week: October 19–25
Give Saturday a social start at Sidetrack
Dog Day Saturday: Halloween Edition
Saturday, October 24 · 1–5 p.m.; costume activities around 3 p.m.
3349 N. Halsted St., Chicago, IL 60657
Sidetrack’s Halloween edition of Dog Day brings pups into the afternoon plans, with canine treats and swag and a costume parade, games and contest around 3 p.m. It’s a straightforward choice if your ideal outing involves meeting friends as well as dressing the dog.
This is a bar event for adults, so leave the family-day-out expectations at home. Choose it for a dog comfortable in a lively social setting; a quieter walk may be a better fit for one who needs more space.
No cover. Human guests must be 21 or older and bring ID; drinks are extra. The listing doesn’t specify event-specific leash or vaccination rules. Check with Sidetrack before bringing your dog, and bring your own ID.
Start with a walk at Dan Ryan Woods
Howl-o-ween 5k – Dan Ryan Woods
Sunday, October 25 · 9 a.m.
Central Picnic Grove #5, 2231 W. 83rd St., Chicago, IL 60620
If your dog would rather sniff a trail than pose for a portrait, this timed 5K run/walk is the most movement-minded pick. Leashed pets can join without a separate registration, and the event benefits K9s for Veterans NFP. Finisher items and treats give the morning its Halloween flourish; you can choose a walking pace instead of treating it as a race.
Choose this one if your dog is already comfortable covering 5K around other people and dogs. The organizer warns of uneven ground when discussing strollers, so this isn’t the outing to choose for a reliably smooth surface.
$45 race entry through October 24, plus processing; the listing currently shows a $3.99 fee, which may vary. Race-day entry rises to $50, plus processing. Packet pickup starts at 8 a.m. Parking is available, and the organizer recommends carpooling. Register before race morning rather than relying on the posted cutoff, which falls after the 9 a.m. start.
Make an afternoon of Wag-O-Ween
5th Annual Wag-O-Ween at Bosly’s Backyard
Sunday, October 25 · noon–4 p.m.
4011 N. Ravenswood Ave., Chicago, IL 60613
Bosly’s gives the afternoon over to more than 20 local businesses, trick-or-treating, a costume contest and pet-photo opportunities. It’s the pick for someone who wants to browse as well as give the dog a Halloween outing. The $15 listed admission includes a tote bag and costume entry, though you shouldn’t assume every portrait or vendor service is included.
A market asks a different kind of patience from a dog than a walk does. Pick it for a dog comfortable around other dogs and shoppers. Humans can also attend without a dog, a useful option if yours would find the bustle too much.
$15 per person as listed by the organizer; final checkout fees have not been confirmed. Admission includes a tote bag and costume-contest entry. Advance tickets are recommended; walk-ins depend on space. Check directly with Bosly’s for event-specific leash and vaccination requirements before bringing your dog.
Wag-O-Ween details and tickets
Next week: October 26–November 1
Join Streeterville’s Halloween morning parade
39th Annual Streeterville Dog Halloween Party
Saturday, October 31 · 9–11 a.m.; parade at 9:30 a.m.
Anne & John Kern Terrace Garden / MCA Sculpture Garden, 220 E. Chicago Ave., Chicago, IL 60611
For a short, city-centered Halloween plan, head to the MCA’s outdoor garden. The Streeterville party welcomes dogs and cats, with a costume parade at 9:30 a.m. and prizes. Arriving before the parade gives you a chance to settle in rather than trying to join halfway through.
This suits a dog comfortable near costumed animals and people. A costume is only worth the photograph if your dog tolerates wearing it; leave room to move and see clearly.
Free admission. The official event page links to an RSVP and donation page. Use the rear gate bordering Lake Shore Park rather than the regular museum entrance. Keep your dog leashed, and bring a dog toy so each dog receives a prize, as the organizer requests. Follow the official page’s RSVP link when planning your visit.
Streeterville party details and RSVP
Take Halloween into the trees in Lisle
Howl-o-Ween at The Morton Arboretum
Saturday, October 31 · 9 a.m.–noon; dogs may stay until sunset
4100 Illinois Route 53, Lisle, IL 60532
The Morton Arboretum pairs a Halloween morning with the option of a longer walk afterward. Parades are scheduled for 10 a.m. and 11:15 a.m., with a costume contest around 10:30, plus trick-or-treating, vendors, pup cups and photos. The organized festivities end at noon, but dog admission continues until sunset.
This is the pick if you want to make more of the day than a single parade. Keep the restrictions in mind: dogs must stay on marked trails, and several gardens and buildings are off-limits, including the Visitor Center and the Children’s and Maze gardens.
$7 per guest dog or $6 per member dog. Nonmember human admission is additional; check the current price when booking. Member humans use their membership. Buy a ticket for each dog as well as any required human admission. Dogs must remain attended and leashed, with vaccinations and registrations up to date. Human portable toilets are available. Check the organizer’s full dog rules before setting off.
Howl-o-Ween tickets and dog rules
Which event fits your dog?
For a dog who likes to keep moving, start with the Dan Ryan Woods 5K, provided that distance is already comfortable. For a sociable dog and an adults-only afternoon, consider Sidetrack. Bosly’s is the browsing-and-costumes option; Streeterville is the shorter Halloween-morning plan. Morton offers the most scope to extend the outing into a walk, within its dog-access rules. These are editorial suggestions based on the settings, rather than guarantees about crowds or how any dog will respond.
Rather skip the costumes?
Horner Dog Friendly Area · 2741 W. Montrose Ave., Chicago. A North Side alternative if you’d rather skip the organized Halloween program.
Montrose Beach Dog Friendly Area · 601 W. Montrose Ave., Chicago. Choose the designated dog area at the north end of Montrose Beach, rather than the ordinary beach or neighboring natural areas.
Both require a current Chicago Park District DFA permit and tag, available through participating veterinarians for $10 per dog for the calendar year. Dogs must be healthy, vaccinated and licensed; puppies under four months and dogs in heat aren’t allowed. Leash your dog before entering and after leaving, supervise throughout, clean up and keep food outside. These are separate outing options, not promises of a walkable stop next to an event. Read our Chicago DFA permit and rules guide.
Before you go
Recheck the organizer’s page before leaving for changes, weather arrangements and ticket availability. Pack water, a leash and cleanup bags. Make a simple exit plan if your dog is overwhelmed, and keep any costume comfortable and easy to remove. All times in this guide are local to Chicago. Listed prices can change; ticket inventory has not been confirmed.
Last reviewed October 17, 2026. Unpublished editorial review draft.
