Why Your Family Needs to Visit Winterland at the Park

One of the things I love the most about the holidays is all of the fun events we Chicagoans can attend, from light shows to breakfasts with Santa. The only problem is that all of these holiday “to-do’s” take a TON of time and effort. I mean, with little ones in tow, you can really only squeeze in one family holiday activity a day when you are dealing with naptime and other family obligations. This year I have found the solution to the holiday craziness helps me check off tons of my Christmas in Chicago Bucket List  in one fell swoop. Where is this magical place? Winterland at the Park at Wrigley!  Yes, that’s right, the gorgeous Park at Wrigley where you go to enjoy sunshine, a game of catch, and maybe a drink or two has totally transformed this winter into the ultimate Winter Wonderland.

This post is sponsored by the Park at Wrigley. All opinions are my own.

Ice Skating

As someone who grew up ice skating competitively, I was so incredibly excited for the day when my boys were old enough to skate. Just a few weeks we had that experience at a different rink and it was pretty challenging. All of our skates were the wrong size, it was extremely crowded, and there wasn’t a ton of railing for fledgling skaters to hold on to. Our experience skating at the Park at Wrigley was the complete OPPOSITE and one that we can’t wait to repeat all winter long.

There were tons of skate sizes for both adults and children to choose from, and the boots were so comfortable and easy to take on and off that even my six year old could do it all by himself. Once we entered the rink, the staff pointed out areas where the ice was a little rocky and also highlighted where the skate hosts were skating around the ice in case of a problem. Clearly safety is the priority at the Rink at the Park, which is something that put this worried mom at ease.

We had such a fun time skating around the 8,000 square feet of ice, admiring both the twinkle lights and historic Wrigley Field towering in the background. And for the Instagram obsessed like me, the clear glass dasher boards were truly perfect for fun and unique photo ops.

Don’t forget that the Rink at the Park is open through February 25th, longer than the Christkindlmarket, and is free for kids 12 and younger. You are allowed to bring your own skates as well, but a skate admission fee still applies for those 13 years and over. There are also Learn to Skate and Curling classes available.


One of our favorite Christmas in Chicago traditions is to head over to the Christkindlmarket for Gluhwein and some European treats. The only problem is that it isn’t just one of OUR favorite things to do…because practically all of Chicagoland is there as well. The crowds can be unbearable, especially when you have kids with you, so take it from me and head to the open and airy Christkindlmarket at Winterland at the Park.

There are fewer vendors at the Park at Wrigley, but trust me, they are fantastic. Whether you are indulging in hot cocoa from Bob’s Belgian Hot Chocolate or digging into a sweet or savory chimney cake from The Stackery, your taste buds will be thrilled. It is the perfect place to indulge in a holiday drink (don’t forget your collectible mug!) or find a delicious sweet treat to fill your family’s stockings.

If you are on the hunt for a unique ornament, there are tons of different handmade options to choose from. Commemorate your trip to Winterland at the Park by picking out a European ornament, or with one of the gorgeous holiday nesting dolls. No matter what you chose, you are guaranteed to find something unique created by the many talented artisans at the Christkindlmarket through December 31st.

Holiday Photo Opps

No trip to Winterland at the Park is complete without some holiday photos in front of the gorgeous lit tree or the beautiful menorah. Standing all bundled up in front of the twinkling lights and authentic European stands sets the perfect backdrop for a holiday card, too.

And if you want to cross one more thing off of your holiday “to do” list, visit Santa at his workshop throughout the weekends until Christmas Eve. When we went to visit the jolly big guy, there was no line at all and we had lots of time to chat with one of the kindest Santas in Chicagoland…and his helpful elves, too!

Park at Wrigley Restaurants and Retailers

Lastly, if Mother Nature rears her ugly head during your visit to the Park at Wrigley, duck into some of the wonderful restaurants and retailers to warm up, enjoy a meal, and finish crossing everything off your shopping list. P.S. The kids’ meals at the Budweiser Brickhouse Tavern are FANTASTIC!

Hope your family has a blast celebrating all that winter has to offer at Winterland at the Park!

Happy Holidays!
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  1. Jeanette says

    I have not been up there in years but it looks like I need to go! It has changed a lot since I have been there last. I would love to go on the ice-skating ring.

    • Amanda says

      Yes, it looks so much different than in years past. And it has been transformed into a winter wonderland…it’s gorgeous!

    • Amanda says

      The Rink at Wrigley is the perfect spot for first timers. Comfortable boots and a rink that isn’t too crowded. Perfection!!!

  2. Emily says

    This looks like so much fun! I have not taken my kids ice skating yet, but it seems like such a fun activity, I need to do it for sure. That Belgian hot chocolate looks amazing!

    • Amanda says

      I swear, I have never had such delicious hot chocolate! I stole a few sips from my kiddos before indulging in my spiced wine!

    • Amanda says

      I love that I don’t have to schlep all over town and that the Park at Wrigley has everything my family needs to celebrate the most magical time of year!

  3. Rach Ferrucci says

    Yes I do need to visit Winterland Park!!! I love everything about this! It’s so festive and has everything you need to have a great time- activities, food, shopping….. what else is there!

  4. Amanda says

    I highly recommend the rink at the park. The skates are great, easy to put on, and the rink isn’t crowded and is well managed. Best skating experience in Chicago!

  5. Amanda says

    And I love that we can cross off so many things off our holiday to do list at once! Santa? Check! Ice Skating? Check! Holiday Shopping? Check!

  6. Sarah Benson says

    We are planning on having a family day in the city on Saturday the 23rd. We have a 13 month old. He will be in a stroller. Do you recommend this over Christkindl? Not sure which would be less crowded. Or maybe we are crazy to attempt either so close to xmas! By the way, I live close to you! I love your blog. 🙂

    • Amanda says

      Hi! When we went on a busy Saturday there was tons of room for strollers during the day. If you are anxious about it, you can always baby wear. Having experienced the markets at both Daley Center and the Park at Wrigley, I would pick the Wrigley location hands down. SO much more family friendly!!! Have a great day in the city! 😉

  7. Elizabeth O says

    Ice skating is so much fun. and it seems that you really had a great time there. I bet that my niece will love to go there after seeing this post. He really wants to play in the snow.

    • Amanda says

      The German market, ice skating, and Santa workshop makes it the perfect spot for Chicagoland families to celebrate the holidays!

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