Weekend in Chicago

My first time to the Windy City and it did not disappoint! Chas and I went to visit his brother, Luke and wife, Ruthie. We had so much fun taking selfies at the Bean, eating Lou Malnati’s deep dish pizza, walking down Michigan Avenue and staying up late playing multiple rounds of Spades.

Explore Chicago | Miss Madeline Rose Lincoln Park in Chicago | Miss Madeline Rose

Lincoln Park is full of the most charming historic homes. This one on the right kind of reminded me of The Parent Trap.

The Signature Room at the 95th | Miss Madeline Rose

If you’re in the Chicago and want a gorgeous (+ free) view of the city I would highly recommend making a stop by the Signature Room at the 95th. Luke told us that he had heard that the ladies restroom has the best views on the 96th floor. He was right! From the beautiful turquoise lake the Navy Pier sits on, to the stunning skyline, it was breathtaking!

What to do in Chicago | Miss Madeline RoseChicago Bean | Miss Madeline Rose

Bernardo Footwear Paige Rain Boot | Miss Madeline Rose

Ruthie took me to one of the largest Anthropologie’s I’ve ever been in downtown. This tile was definitely giving me inspiration. My pink booties are actually rain boots – with the sweetest bows on the back – and were so comfortable and perfect for a long day of walking (just make sure you wear ankle socks!) They come in lots of colors and run a little large, I’m usually a 7.5 and got a 7.

You might have seen on my Insta Stories but this was probably one of the coolest parts of the trip (wink). I mentioned to Ruthie that Giuliana + Bill Rancic had a home in Chicago and we set off to find it! (Mind you it’s currently for sale for 6.8 million, anyone wanna go in together?!) Ruthie and I sat outside of it for a solid 15 minutes. Unfortunately Giuliana was at the Oscars last weekend, but it was still fun to see!

Chicago Style | Miss Madeline RoseGiuliana and Bill Rancic Chicago Home | Miss Madeline Rose

Things to do in Chicago | Miss Madeline Rose

Thankful for the sweetest weekend all together. Chicago was a dream and we can’t wait to go back!

Downtown Chicago | Miss Madeline Rose Bernardo Footwear Paige Rain Boot | Miss Madeline Rose


Look 1: White Tweed Blazer ℅ (fit: wearing a medium), Ruffle Blouse, Urban Outfitters Faux Fur Scarf, Banana Republic Hat, Bernardo Pink Booties (fit: I’m normally a 7.5 and the 7 was a perfect fit), Black Distressed Denim (similar linked), DIFF ‘Barry’ Sunglasses, White Backpack (similar linked)

Look 2: Zady Wool Coat (similar here), Wayf Mock Neck Sweater, Black Distressed Denim (similar linked), Banana Republic Hat, Bernardo Pink booties (fit: I’m normally a 7.5 and the 7 was a perfect fit), Rebecca Minkoff Jumbo Love Crossbody Bag

bloom & grow forever,
Madeline Rose