Windy City Kaitlin

Windy City Kaitlin chicagoland mom sharing lifestyle content and all my favorite things, like books, theatre, disney, and shopping. (fka wishuponastarrynight)

Wish Upon a Starry Night is a lifestyle blog written by Kaitlin Olivero. Featuring all things Disney, art, fashion, and life.

it is a special week in chicago, celebrating the opening of (wish I was going!) and has a special limited edition Barr...
06/18/2026

it is a special week in chicago, celebrating the opening of (wish I was going!) and has a special limited edition Barry Bouquet inspired by 44 himself 💐

the flowers are the lush stems and tones of his official portrait, with airy jasmine vine, presidential blue agapanthus, peach garden roses, white house mums 😍😍😍😍 a thoughtful, joyful bouquet to inspire us dreamers 🫶🏼

only available in Chicagoland from June 15-June 21, so orders yours asap 🙌🏼

i may be slowing down but summer fun is in full swing 😅 also celebrating quite a bit this last week, feeling grateful fo...
06/03/2026

i may be slowing down but summer fun is in full swing 😅 also celebrating quite a bit this last week, feeling grateful for our family and our little life 🫶🏼

ended May with the dreamiest peonies 😍 🌸 outdid themselves yet again, do not sleep on their special events, folks 🫡June ...
06/01/2026

ended May with the dreamiest peonies 😍 🌸 outdid themselves yet again, do not sleep on their special events, folks 🫡
June is a big month for us, with fun stuff on the calendar and the clocking ticking down on our time as a family of four 🥹🤯 wishing you all a month if joy, happiness, and good health 💛

05/28/2026

calling all dino lovers!! 🦕✨🦖
has brought back 25 life sized dinos to make your summer zoo visit even more rawr-tastic! 🦖 you’ll find them throughout the zoo, along with fun photo-ops, and special activities… all included with your daily zoo admission or membership 🙌🏼
so plan a family day (or three) at Brookfield Zoo Chicago this summer to see your animal favs and the DINOS! 🦕✨

05/18/2026

One of my biggest cravings right now? Savory, bold flavored snacks… Thank goodness Hampton Farms at has got me covered! 💚😋

AD just launched their Garlic & Sea Salt Pistachio Kernels 👏🏼 They are roasted to perfection, no shells, and have the perfect kick of garlic 🧄 😌 Natural and satisfying, the best combo! Plus they have 6g of protein per serving 👏🏼
Find these delish pistachios at your midwest Costco today! 💚😋

05/18/2026

we had a very summery weekend in chicago! ☀️ but here is one of my new fav spring outfits that I’ve worn recently 🥰 thank goodness for those buttons on the overalls, giving me a custom fit from week to week 😅

oh and can we appreciate my hair!! freshened up my color and cut… i say this after every appt for the last 10+ years but… she works magic! 🤩

a quieter week around the house, last full week of preschool before a little summer break (ahead of camp!) ☀️also got a ...
05/16/2026

a quieter week around the house, last full week of preschool before a little summer break (ahead of camp!) ☀️
also got a new — the Journey! 😍 it is SO good, very luxe while still being affordable and will grow with our fam (comes with bassinet for baby 3!) 🫶🏼 love this and our twin! use the link in my bio for a discount btw ✨

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806 W. Dundee Rd.
Arlington Heights, IL
60004

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