Visit Chicago, Illinois

Valentines Weekend brought about two single girls, not a care in the world, and memories to tell for a lifetime.

Meet Josie.

Josie and I by the river

We met during Sunday School ten years ago with the common interest of doughnuts. From that moment on I’ve learned she’s always the life of the party and the funniest person you’ll ever meet. She has a heart of gold and goes out of her way for those she loves. Our minds think so much alike we finish each others sentences. She’s my travel partner, encourager, and someone I never fail to have a good time with. All in all, she’s my person.

Which is why she’s always the person I go to first when I say, “I need to travel this weekend. Are you coming?”

We booked a hotel in Naperville, IL Valentines Weekend of 2015, about a month in advance. I wanted to make sure we weren’t going to change our minds, so I was fully aware of the No Cancellation Policy when I clicked “book”. (Dumb move, for reasons described later) We chose Naperville, a little less than an hour out of Chicago. We chose this city so our parents wouldn’t freak out too much about our planned adventure, because it is notably one of the safest places to live in the country. Here’s proof.

The week leading up to that weekend showed snow continuously, but thankfully stopping a few days before we embarked on this adventure. Come to find out, Chicago had just lived through a blizzard that brought along EIGHTEEN INCHES of snow. But our hotel had a no cancellation policy so you better believe the snow wasn’t stopping us. We left by 6am Friday morning, skipping classes and driving six hours. Nonstop talking, changing scenery, and loud rap music (because Josie and I are as gangster as they come) helped time pass. The drive really wasn’t bad and we got to Naperville with plenty of time left in the day to explore the small city. We stopped at Target and spent no less than an hour stuck in traffic, trying to find a place to eat dinner. California Pizza Kitchen was somewhere neither of us had eaten before, and bonus points because they had a Valentines Day special going on. Included in this special was a dessert to share. Who says you have to have a boyfriend on Valentines Day in order to get the good stuff?


Day two we planned to drive to Chicago, until the desk clerk at the hotel gave the recommendation of taking the train instead. No need to find and pay outrageous prices for parking when the train was so convenient. BNSF Railway to Aurora if you ever need it.

Bucket List: ✔Ride a train

Josie and I's first train ride
Josie and I’s first train ride

Once we got into the city, we caught a cab and walked the Magnificent Mile. The Magnificent Mile is literally a mile of retail therapy, restaurants, attractions, and so much more. You can easily spend a full day here because there’s so much to see. Click here for more details and to see what events are going on right now!

Surrounded by skyscrapers
Surrounded by skyscrapers
How excited we were about our first cab ride
How excited we were about our first cab ride

Bucket List: ✔Hail a cab

After we had both drained our bank accounts and got full makeovers at Bloomingdale’s, we grabbed another cab to Millennium Park to see the Chicago Bean.

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Bucket List: ✔See the Chicago Bean


On Sunday morning, we grabbed breakfast (Corner Bakery – highly recommend) and went shopping at an outlet mall as a last ditch opportunity to spend every cent we had. It’s safe to say our shopping in Chicago was a giant success. Our last stop was Giordano’s, the ultimate Chicago Style Pizza.

Bucket List: ✔Eat Chicago-style pizza

We got two pizza’s to go and ate it on our way back to Kentucky, completely content with life and the lack of money in our bank accounts.

Until next time, Chicago.



Bucket List with Kait


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