I’m heading to the incredible city of Chicago next weekend and couldn’t be more excited. Our four day trip is jam packed things to do like chowing down on some delicious grub, catching up with friends, rooting on the Chicago Cubs, sightseeing, and rocking out at the Lollapalooza Music Festival. As usual, I’ll be overpacking – you never know what scenario you might find yourself in on vacation!

I’m most excited for our first night out in the windy city. We’ll be dining out at one of the most sought after new restaurants, Monteverde – praised for its mouth-watering Italian dishes and noteworthy wines from around the globe. The stylish interior calls for a stylish and smart outfit. A simple midi dress and heels paired with a colorful Chloe bag and layered jewels are perfect for the occasion.

We’ll have a much more casual Friday afternoon cheering on our favorite Chicago baseball team and day drinking around Wrigleyville. I’m currently loving the athleisure trend, so what better time to dress sporty chic than at a sports game? Adidas also just re-released the Gazelles, so now’s the time to pick up a pair and show them off.

Saturday is all about brunching, sightseeing, and shopping. Something cute and comfortable will get the job done, so I’m packing up this colorful number from Alicia & Olivia paired with simple denim and sandals.

My boyfriend and I are all over Lollapalooza on Sunday. I’m super stoked to see Local Natives, Ellie Goulding, and LCD Soundsystem just to name a few. I’m especially looking forward to this festival since we’re only going one day. We’ll feel a little less burnt out after our trip while still getting to enjoy music from some of our favorite artists. To wear, I’m packing one of the labels I’m absolutely obsessing over lately, Tularosa. Rompers are so easy and this lightweight one-piece is perfect for festival-going.

Chicago is such a beautiful city, and I cannot wait to get back there next week! If you have any recommendations for our trip, we’d love to hear them!

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