What to Pack for a Weekend Getaway

From left to right starting from top left: chambray tunic | stripe shirt | stripe tee | cropped leggings | white chinos | boyfriend jeans | black blazer | field jacket | graphic tee (similar) | slip-on sneakers | metallic sandals | print scarf | running shoes (updated version) | fitness top | fitness bottoms

My weekend starts today as our family of five packs into our swagger wagon and heads west for a long weekend in Chicago. We go there every year, mainly for leisure but also to get my hair done (will elaborate on this someday soon). I love Chicago because it has all the bells and whistles of a cosmopolitan city but somehow it’s more manageable than NYC. Although I spent over 10 years of my life in NYC, I think suburban life in Michigan has tamed me somewhat.

Chicago has, over the years, turned into the mecca for gastronomic adventures, which is what I live for. Unfortunately, because of the kiddos, I don’t get to try as many restaurants as I’d like to when I’m there. Our time will be spent mostly enjoying kid-friendly activities, eating at kid-friendly restaurants and spending most of our expendable cash at the American Girl store. Alas, I digress.

Well, guess what my job always is when it comes to family getaways? Yes, you guessed it, packing. Packing for myself and everyone else. I hear this weekend, out of all weekends, the temps will be going down to the upper sixties in Chicago. It’s that tricky temperature range that’s hard to pack for. Instead of shorts and tees, I’ll have to pack mostly long pants, long-sleeve shirts and a light jacket since I’m extra sensitive to cooler temperatures.

When it comes to quick getaways, I like to pack light (relatively) and keep my wardrobe neutral and interchangeable. I pare it down to essentials and throw in a couple of impractical items “just in case.” Yes, just in case my husband decides to surprise me with a romantic dinner and show for two while he’s also arranged for a trustworthy and competent babysitter to watch the kids for the night. The chance of this happening…in the negatives, but you never know. I digress again.

Sometimes neutral can mean an ensemble of functional but boring solids and that’s why I like to mix in a lot of stripes. Stripes are an easy way to add a little interest to a neutral wardrobe. I also try to throw in a bit of color via accessories. Comfortable shoes are a must, although I like to bring another dressier pair “just in case.” And lastly, I always bring a set of workout clothes and running shoes “just in case” I decide to go for a run. Now this one has a better chance of happening.

If I’m not debilitated by my girls’ incessant whining, I’ll try to take some pictures and share them on Instagram.

Have a great weekend!

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8 thoughts on “What to Pack for a Weekend Getaway

  1. It’s funny, I absolutely HATE packing…it’s the worst part of traveling for me! And yet for some weird reason I enjoy packing posts? Maybe seeing everything laid out in this fashion on a blog makes packing seem more organized and manageable than it is for me in real life. I can tel you will be looking just as stylish as always in Chicago, and I hope your family has a great time!
    Gina – On the Daily Express

  2. I voted! And good luck to you! I don’t know how you mommies do it all. Great plan for a weekend away! I’m starting to decide what to pack for a week in Portland and along the Oregon coast. Wanna come pack for me? 😉
    Looking forward to pics from your trip!
    Dawn Lucy

  3. This is a FABULOUS packing list! I always really struggle with what to take on any trip and try to pare it down to just the basics that I can pair up differently. I’m saving this for future reference! Enjoy Chicago and eat some good stuff for me. 😉

  4. I’m the worst packer EVER. I honestly need to fill a huge suitcase on just a weekend away.. I know..but I always bring to much shoes.
    I LOVE the clothes over here;)

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