HomeFAMILY TRAVELA Winter Escape to Chicago: Family, Fun, and Fresh Blowouts

A Winter Escape to Chicago: Family, Fun, and Fresh Blowouts

My daughter and I just got back from a whirlwind trip to Chicago, and let me tell you—I am so glad we left right before the snowstorm hit! The city is beautiful this time of year, but the cold is no joke. People often ask how I can stand living in Seattle with all the rain, but honestly? I’ll take drizzles and gray skies over freezing temps and piles of snow any day. I’m a complete wimp when it comes to the cold, and Chicago reminded me of that real quick.

Still, the trip was absolutely worth it. We packed in a full week of fun with family, and I loved every moment of watching my daughter get quality time with her cousins. Since we don’t get to see them often, these visits feel extra special.


Family First

Trips like these remind me why I’ll happily brave a little travel chaos and, yes, even the cold. Watching my daughter bond with her cousins brought me so much joy. They played, laughed, and probably drove us all a little crazy at times—but that’s what family time is all about, isn’t it? Growing up, my cousins were some of my best friends, and I love that she’s starting to make those same kinds of memories.

We spent hours just hanging out in my sister’s house—snacking, chatting, and catching up on life. There’s something about being in your sibling’s home that feels grounding, like you slip right back into old rhythms even if you don’t see each other every week.


A Little Pampering

One of the highlights of the trip was a stop at Blowout Junkie, a blow-dry bar in Chicago. Sometimes you just need a little beauty boost, and this was the perfect treat for both me and my daughter.

I went for their “Signature” style—classic big curls. When they first finished, my curls were tight and super bouncy (as in, maybe a little too much volume). But after a couple of hours, my hair settled into these gorgeous, soft waves that framed my face perfectly. It gave me that effortless, put-together look that we all wish we could wake up with every day.

My daughter chose the “Junkie Wave,” which gave her loose, beachy curls. It was such a fun style for her—youthful and playful while still polished. Honestly, I think she loved the experience of getting pampered just as much as the hairstyle itself. Sometimes mother-daughter outings like these are just as special as the big family gatherings.


City Vibes (and Cold Realities)

Chicago is such a vibrant city, and even in the winter chill, you can feel its energy. The food scene alone is worth the trip (deep dish pizza, anyone?), and there’s always something happening. But every time I’m there in the colder months, I’m reminded of how much I value my mild Seattle winters.

Walking around the city bundled up in layers, I found myself constantly thinking, How do people do this every day? Hats off (well, not literally, because it was way too cold for that) to the locals who brave the freezing winds and snowstorms with such ease.


Making the Most of Every Visit

Traveling to see family always feels like a balance—trying to fit in as much fun as possible while also giving yourself space to just be. This trip was a good reminder that you don’t always need a packed itinerary to make it memorable. For us, the highlights were simple:

  • Cousin time full of giggles and games.
  • Sister catch-ups over coffee while the kids ran wild.
  • A little beauty treat that made us feel fabulous.
  • Escaping before the snow trapped us inside!

Sometimes, the best vacations aren’t about the sights you see but the people you’re with.


Back to the Rain (Happily)

Now that we’re home, I find myself grateful for Seattle’s mild drizzle. Rain might not be everyone’s favorite, but after spending a week bundled in coats, scarves, and boots, stepping outside into cool but not freezing air feels like such a luxury. Give me my umbrella and a cozy sweater any day.

Chicago gave us memories, laughter, and curls that lasted just long enough to make the photos extra fun. It also gave me a renewed appreciation for family time—the kind that fills your heart even as your fingers and toes are still thawing out.

Until next time, Chicago. Next visit, though? Maybe we’ll plan for spring.

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