My Perfect Chicago Itinerary

This post has been sponsored by Diet Dr Pepper and Jewel-Osco. As always, all thoughts and opinions are my own. Thanks for supporting the brands that make Charmingly Styled possible!I LOVE weekends, like big hearts, #1 fan, can we have weekends all the time love. It’s not just because I don’t have to go into work but because I’m able to get to explore new neighborhoods in Chicago, and continue to refine my list of favorite places to explore. And believe me, even after living in Chicago for almost 5 years, there’s still so much to explore.

So on a work-free Saturday, I like to spend the day hitting up a few of my favorite spots in the city, from my favorite coffee shops, streets for shopping and places to take in the prettiest views of the city. If I happened to have a full day free in Chicago, here’s the perfect way I’d spend my day off.

Morning Coffee In My Neighborhood: 

The best days start by sleeping in until 9 {or 10, or 11!} and hitting up my favorite coffee shops in Lincoln Park. There’s nothing more relaxing then easing into your day, and spending your morning sipping in a big latte or chai tea. Since I’m a self-described workaholic, I usually spend weekend mornings at coffee shops listening to music, treating myself to a croissant and getting things checked off my ever growing to-do list. But when you spend the morning in a coffee shop this beautiful, you really can’t be too mad, right?!Lunch with my Favorite Gals: 

Clearly I’m a very food motivated person, so after a few hours hanging at a coffee shop, I love to get together with a few girlfriends and grab lunch. Since not everyone else is as eager to spend the morning doing work, I always find it easier to do lunch or a super late brunch on the weekends so everyone can get up on their own terms. I love grabbing lunch in the West Loop neighborhood, which is known to have the most insanely delicious restaurants and hangouts – including one of my favorites, Chicken Shop in SoHo house! Shopping on Armitage Avenue: 

After a day full of productivity and hanging with my friends, I usually find myself on Armitage Avenue on a Saturday afternoon, swinging by all my favorite shops {including some local gems!}. The weekend’s never complete without treating yourself to a little something, but I still try to exert some self control when it comes to shopping. Did I maybe buy this new shirt on a recent weekend shopping adventure? Maybe…but I definitely don’t regret it 😉   Enjoying an afternoon Pick-Me-Up: 

After being coffee-free since my morning cup, I usually need a little pick-me-up before the 3PM crash hits. Rather than grabbing another cup of coffee, I usually opt for a Diet Dr. Pepper from my local Jewel-Osco {you can find your closest one here!}, which is the perfect sweet reward for a busy afternoon. I love that it’ it’s guilt-free {yay diet drinks!} and gives me a little caffeine kick that I need to keep moving throughout the rest of my afternoon and night. Even on work-days when I can’t hit the grocery store, I’ve been packing a smaller Diet Dr. Pepper with my in my purse with a few of my work essentials, and it’s definitely my new favorite way to keep me motivated on the toughest of long work days.  My Favorite Chicago View: 

While lots of Chicagoans feel like Cloud gate {aka, The Bean} has a lot of hype around it, I’m still a big fan of stopping by to take a few snaps whenever I have a few hours to myself. When I moved here years ago, it was like a magical symbol to me that I made it in the “big city”, and since then I must have taken at least 100 photos of it over the years. Sure, it’s a little excessive – but if you’ve ever seen The Bean up close, you’ll see why it’s one of my favorite spots in the city. Millennium Park is the perfect place to explore if you have a few spare hours, and I love ice skating in Maggie Daley Park {a smaller park withinMillennium Park} and then hitting up Chicago Athletic Club to take in the views of downtown Chicago. I mean, you can’t really beat that view! What’s your favorite way to spend a day off in your city? I’m always looking for new cities and neighborhoods to explore! xx

  • This is the perfect day to spend in the city! You make me want to take a long overdue weekend trip!

    • Please come visit soon! I would love to take you around my favorite Chicago spots 🙂

  • My family is coming to visit for the first time this weekend and one of our stops is going to be at Chicken Shop to celebrate my grandma’s birthday! (she requested chicken lol) It will be my first time and I can’t wait! p/s we’re jacket twins 🙂 Happy Wednesday, girlfriend!

    26 and Not Counting

  • This is a great weekend plan! I’m also the weekend’s #1 fan, it’s the best time of the week! 🙂

    xo, Sarah

    • Can we weekend all the time?! Excited to see you SOON!

  • Such perfect weekend plans and I need to get back to Cindy’s! Sad I’m missing you tonight 🙁