You probably already know this is one of my favorite cities. Although it is windy it is beautiful especially during the winter holidays. I did a girl’s trip in December and enjoyed seeing the holiday displays and way too much shopping.
A great day in my shoes is filled with brunch, shopping, dinner and bar hopping! So please prepare to dress in layers, yes wear the cute fluffy hat and sensible shoes. My Booties are my go-to for all trips, spoiler I own them in black, white and tan. With that know that I spend September – March in a pair of these. They are comfortable, stylish and universal. Which fits my time capsule style to a tee!
Brunch is a must at Santa Monica Summerhouse, its bright with a glass roof and filled with greenery. The bakeshop when you walk in has the best sweet treats and you can taste something new.
The magnificent mile is well…magnificent you can easily see how it earned the name. I would say any store you need is within walking distance. I am typically a big on-line shopper, but the downside is that you don’t get to see what is being styled and all of the options like you do in the physical store. When in Chicago it is a must go shopping move. Hint Hint…every store carries different items.
Time Out Market is like a classy food court. I fully support these markets, there is also one in Boston, check out my post on it! These have rotating chefs and restaurants so every time you go there are different options to choose from!
Once you leave here stop in to Blind Barber which is a speakeasy that I found on another trip to Chicago and I find it to be so cute and quiet inside. Speakeasies to me are hit or miss for me, sometimes they are over dramatized and others are just really not that cool. This is not one of those.
It is officially the fun fun part now, Federals for tequila shots! Or not, but this place is known for them because they are served in ice shot glass’s which you then get to throw at the large bell. It is quite the experience in itself and worth suffering through or enjoying the tequila!
Chicago is just a great weekend away, with many options for dining, shopping and site seeing.
