A First-Timer’s Guide to Chicago!

Happy happy Wednesday! It seems a little funny to be sharing my travel guide to Chicago while I am currently in New York- but such is my crazy life this week! 

Earlier this month I took my first-ever trip to Chicago (eek!!) and I must say, it didn’t disappoint in the slightest! I had always heard that I would love it, but I had not idea what to expect. It is such a pretty and clean “big city” (and if you know New York then you know this is a pretty novel concept) and there is so much to do/see/eat/explore- I don’t know how you could ever get bored! I’m lucky that one of my gal pals, Stephanie, lives there so I was able to stay with her & her sweet family and galavant around the city to my heart’s content!

So for any of you Chicago first-timer’s- today’s post is for you! And if you’re a seasoned visitor then tell me your “must sees” and “must do’s” – I’m already planning my next trip back! 🙂


I mean, is it really a trip to Chicago if you don’t stop by and see the famous Bean statue in Millennium Park? I’m going to say no 😉 Of course I dragged Steph with me to this touristy destination- and it was just as fun (and reflective!) as I had hoped! TIP: Make this one of your first stops of the day to avoid the major crowds in the afternoon. We got there around 10:00 am and were able to get right on up and take our pic!


Even though it was a rainy and drizzly day, we were still able to take in the gorgeous Lake Michigan views! The little sailboats looked so picturesque and like a painting come to life! When the weather was nicer it would definitely be on my list to run here! TIP: For everything you do in the city- wear comfortable shoes! Trust me, you don’t want to mess this up 😉 #BlistersAreNoFun


Another item on my wish list was shopping the famous Magnificent Mile. I mean how can a shopaholic blogger resist?! 🙂 It’s much as I dreamed it would be, shop after shop after shop of fabulous stores and cute items! I managed to walk away with only 2 items- but that’s only because my carry-on was already packed to the max! TIP: Magnificent Mile packs in a ton of your mainstream stores, so if you’re looking for those unique boutiques make sure to research those ahead of time (I plan on seeking those out next time).

Spotted on our walk… Steph explained to me how big of a deal it was that the Cubs are so close to the World Series and they had these fun scarecrows all over the block to commemorate this fun time in sport’s history!


The other big item on my wish list was visiting the famous “Rose all Day” sign at Hampton Social & I was one happy girl to cross this one off my list! The rose is just as good as you’d think it would be, and their flatbread pizza was a perfect pick-me-up app after all our walking and shopping! TIP: Go in the early afternoon to avoid the bustling nighttime crows (and to get the perfect Instagram shot)!


Steph booked us reservations here ahead of time as it is one of the new “hot” restaurants in town and it didn’t disappoint in the slightest! Most of the food is southern-cousine with a twist and I pretty much wanted to try everything on the menu! I ended up going with a Banana Slammer Cocktail and a Pimento Cheese Burger for dinner and they were both to.die.for. We also enjoyed fried pickles for an appetizer and they were some of the best I’ve ever had! TIP: Go hungry… you’re going to want to enjoy all the restaurant has to offer!


Since Saturday ended up being very rainy and we had planned to hang with Eden all day (Steph’s 15 mo daughter) the aquarium seemed like the perfect day activity! We decided to just buy the entry-level tickets (since 15 month olds have short attention spans) but it was the perfect amount of exhibits to investigate and explore before Eden needed a nap 🙂 TIP: There is a much shorter entrance underground for families with strollers!


After dinner at Nosh and Booze we wanted to get our dancing on… and since some of my Florida gal pals happened to be in town this same weekend (#GreatCoincidence) we met up at The Fremont for drinks and booty-shaking! I am not kidding when I say that the DJ there was the best I’ve ever heard! Think early 2000’s hip hop mixed with today’s hots- it was amazing and I couldn’t stop shimmying and shaking my groove thing! 😉

My girl gang- these ladies are the best!


Sunday morning we took Eden to a fall festival at the zoo and it was just the perfect way to ring in fall! There was a serious chill in the air and pumpkins everywhere- this girl was in heaven! There are also lots of sweet animals to see 🙂

Bonus: there are also amazing views of the city from the zoo!

Whew! If you made it to the end of this post- BRAVO! I hope I gave you some insight into the amazing city of Chicago and guidance for your next (or first trip)! I loved my time in the city & if you have any questions at all, please ask!



  1. October 26, 2016 / 12:43 pm

    You had a great trip to Chicago! The Bean and Magnificent Mile are two musts in my book as well. I love, love, love Chicago but I haven't been since college… I need to get back up there soon!

  2. October 30, 2016 / 6:19 am

    looks like you had such a great trip! would've loved to visit the Rose place ( just for the sign)! 🙂

    Metallic Paws

  3. October 31, 2016 / 10:56 am

    Such an amazing recap girl!! This makes me want to visit chicago again and soon!! I love that Rose place – I want to visit for a picture there LOL! xo, Biana –BlovedBoston

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