Visit Chicago, IL

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

Meet Josie.11377250_10155762988125252_756707547866048298_n

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, 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 with nonstop talking, changing scenery, and loud rap music (because Josie and I are as gangster as they come). 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 they had a Valentines Day special going on that included a dessert to share. Who says you have to have a boyfriend on Valentines Day in order to get the good stuff?

Now, one of the main reasons for our trip was to go to a few 18 and up nightclubs, because dancing and hot boys, am I right?

How naïve of us, but you live and you learn.

Long story short, the nightclub that we went to the first night was SKETCH. We sat in the parking lot watching people go in for about 20 minutes before we decided that wasn’t where we needed to be. Thinking back, anyone 21 and older would most likely never be caught at an 18 and older club (and if so, red flag), so why Josie and I thought we would meet our soul mate at a place like this is beyond me. Only those in the awkward years of 18, 19, and 20 would be there, which was fine because that was us, too. But emphasis on the “awkward.” We just wanted to dance and have a good time with decent people we’ve never met before. And because Chicago is a bigger city, we thought the clubs would have more of a fighting chance to be “decent” versus any place in Kentucky. This first night proved us wrong, but since the temperature was in single digits, we didn’t complain too much as we drove back to our warm hotel room.

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.

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

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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After our feet were close to freezing off (16 degrees F isn’t the desired temperature to spend the day outside) we caught the train back to Naperville to get ready for our second attempt to get jiggy on a dance floor.

This night club, called Madusa’s (already sounds hopeful, doesn’t it?) was a good 20 minute drive west of Naperville. No big deal though because we were determined! There was a line out the door with a bouncer checking ID’s. Yes! Finally! Something legit!


Picture this –

You walk into a room with music so loud it’s rattling your insides; teenagers surrounding you who look too young to be here, wearing too little clothing and where are there parents right now?; in a room pitch dark and in between each strobe light you see girls twerking on stage with neon pink fur ugg boots that go up to their knees.

This was too much for our senses. Our last straw was when a guy at least 2 inches shorter than us tried to hit on Josie. We needed to high tail it out of there ASAP. And after flirting with the bouncer to try and persuade them into letting us into the 21 and up area, to no avail, we were on our way back to the hotel room once again.

Another full face of makeup gone to waste, but how could we protest when we had just had the comical night that we had? I know you’re saying “what did you expect?” and to that comment I completely oblige. But to be fair, I’m writing about this adventure and laughing as I type because it happened. Life is too short not to at least say you tried!

On Sunday morning, we grabbed breakfast (Corner Bakery – our new favorite restaurant) 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. 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.

Oh but the story isn’t over yet.

After getting back to everyday life, two months later a letter comes in the mail addressed by the state of Illinois with a bill of $278.

When you realize the fun is over and you have to pay the state of Illinois all you have in your bank account

Come to find out, you have to pay the tolls even if humans aren’t there to collect your money. (Face palm)

Josie and I had never driven through a toll before so we honestly had no idea we were doing anything wrong. We always followed the car in front of us, which seemed to always go through the EZ pass lane. Good thing our bank accounts had had a little time to recover from our shopping binge in Chicago. Now to cough up every single toll we missed times 20.

Definitely a dumb mistake, but we learned the hard way. This trip was filled with so many memories to look back on and laugh. Until next time, Chicago.



1 thought on “Visit Chicago, IL

  1. I’m dead at your toll story hahahaha!


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