Rally the corgi has sniffed out the Christmas events for kids in Oswego for 2026, both from the Oswegoland Park District. Kids ride the Oswego Holiday Express in their pajamas to meet Mrs. Claus and Santa at South Point on December 11, 12 and 13, and Santa phones registered children at home on Tuesday, December 15. We check every date on the host’s own website and link straight there. For the rest of the state, see our Illinois Christmas events for kids guide.
What Rally found in Oswego
- 2 Christmas events for kids in Oswego
- Oswego Holiday Express: December 11, 12 and 13, sessions from 2 to 7:30 pm
- Santa on the Line: Tuesday, December 15, calls from 6 to 8 pm
- Both need registration with the Oswegoland Park District
- Every date checked on the park district registration site on Nov 11
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Rally’s Christmas research
Rally the corgi has 1 more Oswego event researched for you.
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Ticketed and paid Christmas events for kids in Oswego
Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.
Event hosts: free events are listed first. The #1 spot puts your event at the top of this page.Inquire about the #1 spotAdd your event for free
Pajama trip to see Santa
Oswego Holiday Express
- When: Friday, December 11, 2026 (4:30 and 6 pm sessions), and Saturday and Sunday, December 12 and 13, 2026 (2, 4 and 6 pm sessions). Each session lasts 90 minutes.
- Where: South Point, 810 Preston Ln., Oswego, IL 60543 (opens in maps)
- Cost: $25 residents, $35 nonresidents; $10 off for children 2 and under
- Ages: All ages
Expand to see the parent tip
Kids board a holiday shuttle at South Point in their coziest pajamas for a pretend trip to the top of the world, where Mrs. Claus welcomes them and Santa waits to say hello.
Hot cocoa from the Village Grind is part of the visit, and shuttles leave every 20 minutes during each 90-minute session, so the wait stays short.
Parent tip: Everyone needs a ticket, from grandparents to babies. Refunds end December 1, and wheelchair-accessible shuttles run on the Friday evening sessions only.
- Host
- Oswegoland Park District (opens in a new tab)
- Address
- South Point, 810 Preston Ln., Oswego, IL 60543 (opens in maps)
- Confirmed
- On the host’s page, checked
New Oswego events every week
Rally researches Christmas events in Oswego daily and updates this page with new events. Enter your email to get a weekly update with new events in Oswego.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Oswego event researched for you.
- New events every week We research new events daily and send you one email a week with the new ones we find in Oswego.
- Exclusive access to free events Find the free Christmas events in Oswego before they fill up.
- Unlock the filters Find Santa visits, free events and weekend plans in one tap.
- Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
- One-tap add to calendar Save any event to your Google, Apple or Outlook calendar so you never miss it.
Coming up on this page
- 2 Santa
Enter your email to get new Christmas events in Oswego every week.
Phone call from Santa
Santa on the Line
- When: Tuesday, December 15, 2026, Santa calls between 6 and 8 pm; register by December 10
- Where: Phone call to your home, Oswego, IL 60543 (opens in maps)
- Cost: $7 residents, $10 nonresidents, per child
- Ages: All ages
Expand to see the parent tip
Santa sets aside an evening to phone children around the Oswegoland area, asking how their year went and what is on their Christmas lists.
After you register, the park district emails a short survey so Santa knows your child’s name and a few details before he calls.
Parent tip: Registration closes December 10, the survey arrives December 11, and it must be returned by December 13 or the call will not happen. Register each child who wants to talk to Santa.
- Host
- Oswegoland Park District (opens in a new tab)
- Address
- Phone call to your home, Oswego, IL 60543 (opens in maps)
- Confirmed
- On the host’s page, checked
New Oswego events every week
Rally researches Christmas events in Oswego daily and updates this page with new events. Enter your email to get a weekly update with new events in Oswego.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Illinois Christmas train rides page.
See every event on a December calendar
Plan your December
When each Oswego Christmas event for kids happens
Pick a Holiday Express session early, since tickets are per person and refunds end December 1. Sign up for Santa on the Line by December 10 and watch your inbox for the survey.
- Oswego Holiday ExpressOswego · Dec 11 to Dec 13
- Santa on the LineOswego · Dec 15
Looking further afield? Our Illinois Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Aurora, Naperville, Romeoville and Shorewood. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.
Buy on AmazonKeep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Illinois city.
Oswego Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Oswego this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Oswego for 2026, both from the Oswegoland Park District: the Oswego Holiday Express on December 11 to 13 and Santa on the Line on December 15.
When is the Oswego Holiday Express in 2026?
Friday, December 11 (4:30 and 6 pm), and Saturday and Sunday, December 12 and 13 (2, 4 and 6 pm), at South Point, 810 Preston Ln. Each session runs 90 minutes.
How much is the Oswego Holiday Express?
$25 for residents and $35 for nonresidents per person, with $10 off for children 2 and under. Everyone attending needs a ticket.
How does Santa on the Line work?
Register each child by December 10 for $7 (residents) or $10 (nonresidents), fill out the survey emailed on December 11 by December 13, and Santa calls between 6 and 8 pm on Tuesday, December 15.
Who do I contact about Oswego holiday events?
The Oswegoland Park District at info@oswegolandpd.org or 630-554-1010.
Are there Christmas train rides for kids in Illinois?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Illinois Christmas train rides page.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked Oswego on November 11, 2026. Rally is also contacting each organizer to confirm details like parking, restrooms and bad-weather plans.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.