Striped Shirt (exact sold out, but I love this classic one and this fun one too!) // Hudson Jeans // Tassel Flats (love these ones too!)  // Vera Bradley Gallatin Satchel

Chicago has always been a special place to me – ever since I was a little girl growing up in Madison, Wisconsin. In the Midwest, Chicago is the “Big City”, the place you’d go to for special occasions (birthdays, vacations, milestones, you name it), and it was always my big girl dream to live there one day. There are still mornings I wake up, 5 years later, and have little pinch me moments. I’m still in awe when I drive back into the city and see the skyline, or find myself on a rooftop taking in the view of the city. And while I love it all year long (maybe love is a strong word in the middle of winter…), fall is definitely one of my favorite times of the year to be in Chicago.  Besides the weather being beautiful, there are so many amazing things to do in the city that make me appreciate the season and Chicago even more. While I’ve honestly not been able to cross too many things off my fall bucket list this year – there have been a few highlights that you should do if you’re in the city too!

Visit a Farmer’s Market: Farmer’s markets in the city are awesome in the summer, but they’re still worth a trip in the fall. I love the Logan Square farmer’s market (especially this time of year) and always stock up on apples, cider and everything your little fall-loving heart could possibly want. I’ve also been picking up eucalyptus to add a little greenery to my apartment when swapping out flowers is too tough (and expensive too!)

Swing by a Festival: Chicago has at least a few festivals every weekend – and the fall ones are pretty awesome too. I made it to Apple Fest and Octoberfest this fall, and both were entertaining in their own ways 🙂

Enjoy some Chicago sports: Tom and I made it to both a Cubs game (he called it a Brewer’s game as a true Wisconsinite!), and a Black Hawks game this fall, both of which were so much fun. We scored some pretty epic Blackhawks tickets and ended up in the third row (it was CRAZY!), but any seat in the stadium is just as fun. While I’m not usually very sporty (….at all…), going to a few games a season is the perfect amount of entertaining for me!

Visit an Apple Orchard (And/Or Pumpkin Patch): Luckily there are a ton of apple orchards or pumpkin patches just a little outside the city, so getting out of town isn’t too tough to accomplish. Based on how quickly the weeks have gone by, I haven’t been able to make it to one quite yet – but I’m hoping to plan a super fall fun day with friends next year that includes an epic trip to an orchard, a winery tour and anything else that makes you feel like it’s fall, ya’ll 😉

Eat ALL the Pumpkin Donuts: the eternal question in the fall is if you’re a pumpkin donut person, or an apple cider donut person. While both are delicious in their own right, I personally have a pro-pumpkin donut agenda (pumpkin spice everything, right?). I’m open to taste testing other options, but I have to have at least a few pumpkin donuts every fall to celebrate right!

Also Eat ALL the Pumpkin Spice Things: I may or may not have gone to Trader Joe’s at the beginning of the season to buy ALL their pumpkin spice goodies – and I have zero regrets about having a pumpkin spice version of most products in my fridge and pantry. My love for pumpkin spice everything is very, very real (except to a PSL from Starbucks, that drink is bananas – I can only muster up the ability to have one every season!)  My love of fall also extends to my wardrobe, since it’s one of my favorite seasons to dress for.  Summer is fun when you can wear sundresses, but I’m a jeans lover at heart – which makes me a little meh about ever feeling cute in shorts. Whenever I can bust out jeans and a long sleeve striped t-shirt, I always feel in my element.

I love this Vera Bradley Gallatin Satchel for fall, especially the rich red leather that I love. Red is always one of my favorite colors, and I’ve found that a red purse is just as versatile in my wardrobe as a neutral brown or black bag (and it adds a much needed pop of color too!) It’s big enough to fit all me essentials in (phone, wallet, iPad even)  – and you can wear it as a cross-body bag to hold it by the handles for a different look. It’s a super fun purse for fall (especially paired with a red striped shirt!), but I’m sure I’ll be rocking it every other season too!Even though I’m singing Chicago’s praises when it comes to fall, I’m a little bit of a hypocrite since I’m actually in Barcelona right now! We’re getting adjusted to the time change, but trying to fit as much adventure in as we’re getting acclimated. Hopefully I’ll be sharing some fun Instagram stories, so follow along to get a peek at our trip around the city! xx