Top 10 Ice Skating Rinks for Kids and Families

When the temperature drops and the snowflakes start falling, we all start looking for those magical winter activities in Chicago to keep the kids entertained and burn off some of that holiday cookie energy. And what better way to embrace the season than ice skating? It’s fun, festive, and the perfect excuse to bundle up in something fabulous while holding hands with your little ones as they wobble across the ice.

Let’s glide right into our favorite ice skating rinks in Chicago that offer something for everyone—from adorable beginner-friendly spots to grand destinations that make you feel like you’re skating in a winter wonderland.

Best Ice Skating Rinks in Chicago

From iconic downtown spots to hidden neighborhood gems, Chicago offers skating destinations perfect for families. Let’s lace up our skates and dive into the most magical places to glide this winter.

1. Maggie Daley Park Skating Ribbon

When it comes to Chicago skating spots, Maggie Daley Park’s Skating Ribbon is practically iconic. This winding path offers a unique twist on the traditional rink, making it feel more like a magical winter trail. Plus, it’s surrounded by twinkling lights and the jaw-dropping Chicago skyline.

Why You’ll Love It:

• Free admission (you’ll just need to rent skates if you don’t have your own).
• Perfect for both beginners and seasoned skaters, thanks to its spacious layout.
• Cozy refreshment areas for warming up with hot chocolate.

Pro Tip: The lines can get long, so try booking a reservation online. And while you’re there, outfit your little skaters in the cutest, warmest gear from Lola and the Boys. Our Rainbow Star Winter Puffer Jacket is the perfect blend of style and comfort for chilly adventures.

2. Millennium Park Ice Rink

Right next to the famous Bean (yes, it’s called Cloud Gate, but let’s be real, it’s the Bean), this rink is a must-visit. Skating here feels like you’re part of a Hallmark movie, complete with holiday lights and a lively downtown vibe.

Why You’ll Love It:

• Located in the heart of downtown, so you can easily turn it into a full-day outing.
• Admission is free, and the rink also provides complimentary "Learn to Skate" lessons. Skate rentals are included at no cost for those participating in the lessons.
• Perfect Instagram-worthy setting with the Bean in the background.

Pair this magical experience with the Emoji Beanie will keep your kiddos warm and oh-so-cute while they show off their moves.

3. Gallagher Way Rink

Tucked next to Wrigley Field, this cozy skating spot screams charm. It’s a smaller rink, which means less intimidating for beginners (and fewer “I’m going to fall” moments for us moms).

Why You’ll Love It:

• Family-friendly atmosphere with a focus on making skating fun for all ages.
• Plenty of nearby restaurants and cafes for a post-skate treat.

Gallagher Way also hosts a Winterland celebration with festive vibes to keep the holiday spirit alive. Dress the family in Lola and the Boys’ Tie-Dye Joggers for a cozy and stylish look before hitting the ice.

4. McCormick Tribune Ice Rink

Located in Millennium Park and offering a traditional oval rink, the McCormick Tribune Ice Rink provides a classic skating experience. It’s a top pick for tourists and locals alike who want to enjoy winter activities in Chicago with a dash of holiday spirit.

Why You’ll Love It:

• Free skating admission; just rent your skates and go!
• Close proximity to other downtown attractions, like the Art Institute of Chicago.
• Group lessons are available for kiddos (or moms!) who need a little extra help.

Pro tip: Pair your adventure with warm winter layers. The Teddy Velour Set will keep your kids snug while looking picture-perfect for all the family photos you’ll take.

5. Fifth Third Bank Winter Wonderfest at Navy Pier

If you want something more than skating, head over to Navy Pier for their Winter Wonderfest. It’s like stepping into Santa’s workshop, complete with holiday rides, indoor snow activities, and of course, a fantastic ice rink.

Why You’ll Love It:

• It’s indoors, which means no freezing toes!
• Tons of extra winter activities to keep the whole family entertained.

Style Tip: While the rink might be indoors, you’ll still want to dress the kids in cozy layers. The Sparkly Rainbow Sweatshirt is ideal for staying comfy and chic.

Tips for Preparing to Go Ice Skating with Kids

Ice skating is a fun and memorable activity for the whole family, but a little preparation can make the experience smoother and more enjoyable. Whether it’s your first time or you’re seasoned skaters, these tips will help you get ready for a great day on the ice:

1. Dress for Warmth and Comfort

Even if the rink is indoors, it can get chilly, so be sure to layer up!

• Opt for insulated jackets, gloves, and warm socks to keep everyone cozy.
• Avoid overly bulky clothing, which can make it harder to move freely.
• Don’t forget hats or headbands that cover ears—cold ears can quickly ruin the fun!

2. Choose the Right Skates

• If you have your own skates, check that they fit well and are in good condition.
• Renting? Arrive early to ensure you get the right sizes for everyone. Most rinks have staff to help you pick out properly fitted skates.
• Double-check that the laces are tight and provide adequate ankle support, especially for little ones learning to skate.

3. Safety First

• Make helmets a priority for younger kids. A lightweight bike helmet works perfectly!
• Gloves aren’t just for warmth—they’ll protect little hands if they fall.
• Go over basic safety rules, like keeping a safe distance from others and learning how to fall and get back up safely.

4. Pack Essentials

A well-packed bag can save the day! Be sure to bring:

• Extra socks: Wet feet are no fun!
• Snacks and water: Ice skating can be tiring, so refuel as needed.
• Small first aid kit: Just in case of minor scrapes or blisters.

5. Prepare Kids in Advance

• If it’s their first time, explain what to expect, like how slippery the ice will feel and the importance of holding onto the railing at first.
• Encourage them to bend their knees and take small steps—gliding comes with practice!
• Remind them that falling is part of the fun and nothing to worry about.

6. Arrive Early and Take Breaks

• Skating rinks can get crowded, so arriving early ensures you’ll have time to settle in and get comfortable.
• Don’t push kids to stay on the ice too long; short breaks will help keep their energy up and avoid frustration.

7. Make It Fun!

• Turn it into a game, like practicing balance challenges or seeing who can glide the farthest.
• Cheer on their efforts, whether it’s their first time standing up on skates or mastering a smooth glide.

With a little planning, your ice skating adventure can become a cherished family memory full of laughter and joy!

Trendy Clothes for Your Ice Adventures

Before your family heads out to explore all the fabulous ice skating rinks in Chicago and check out the best Chicago skating spots, make sure you’re dressed to impress. At Lola and the Boys, we’ve got everything you need to stay warm, comfortable, and stylish this season. From adorable winter puffers to cozy beanies and playful sweaters, our collection is designed with moms and kids in mind. Shop now and get ready to hit the ice in style!