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Jet Set: Chicago

Jet Set: Chicago

Welcome to a new series we'll be doing all about summer travel! We'll be giving you tips all about what to wear and see at destinations all over the world. So grab your phone, some sunscreen, and comfortable shoes because here we go!

First on our stop we're going somewhere near by, but far enough to feel like you're in a whole new world. If you haven't guessed it, you didn't read the title. It's Chicago!
Chicago is only a 5 hour drive or a quick plane ride up north. Whether you're roadtripping it or not, it's always good to keep a journal of all that happens.

We love this one. You can also snap pictures and post them in here for more of a scrapbook feeling!

 Winks Personal Journal ($16.50)

Now what should you fill your journal with? Oh yeah! Here are some places in Chicago we love:

Wrigley Field

Chicago Illustrated Art Print Rifle Paper Co. City Print: Chicago ($36)

Wrigley Field is a great spot to relax with some friends or family and catch a baseball game. Not to mention, it's one of the older buildings in Chicago, so there's tons of history there! 

What to Wear

Summertime is probably the best season to go to Chicago- because you can wear whatever you want! Tempuratures usually range from 79°-84°, making outdoor activites like baseball very popular.

This outfit is our idea of a homerun. The cold shoulder top is light and comfortable, which makes it perfect for a game. Pair it with a jean skirt to add some structure to your outfit and finish off the look with these comforatble flats. Never forget to accessorize, dolls. Add a pop of team and home spirit with this ball cap. Only locals will know what 'SDF' means, right? The color is all that matters, but it is a sneaky way to give homage to Louisville. Add this crossbody purse to carry goodies and your wallet in, but don't forget to add some sunglasses just in case you sit on the side where the sun is right in your face.  

All these goodies can be found here:

Striped Cold Shoulder Top- Ivory
Edgy Fray Demin Skirt
Silvia White & Silver Sandal
Genesis Quay Australia Sunglasses
Gold Chain Shoulder Bag- Black
SDF Aviate Hat- Red

Millennium Park

Millennium Park is this huge park in Chicago that is great for summertime exploring. It's right on Lake Michigan, so the breezes will be fabulous for a wind-swept Instagram-worthy picture in front of the bean. 

What to Wear


In Chicago, you'll do a fair share of walking, so sticking to a comfortable pair of shoes is a good idea. These sandals are a great comfortable and stylish solution to this requirement. We love this romper for summer! It's very light weight and breezy, which is perfect for the windy city. To tie the outfit together, we suggest some light jewelry. These earrings add some glamour to the ensamble, so of course we love them!

Find these pieces here:

Cadrian Romper
Abby White & Gold Sandals


When you're in Millennium Park hit stops like the bean, the beautiful gardens, and water fountains. Hopefully, the weather is perfect for a few hours exploring!

Some other tips for traveling in Chicago are:

  • Always carry an umberella! Even if it's not raining, umberellas provide instant shade on a hot day.
  • Consider packing a sweater or cardigan. Even though most days are warm, you never know when a storm will arise and bring in cold air.
  • Layers are key! Think about how adding a layer can create a whole new look. 

That's all for now, happy traveling!


Dress & Dwell

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