How to: Chicago

Please enjoy this tutorial of how to take on the city (and suburbs) of Chicago.

Before you go: Plan a trip to celebrate the end of your internship (and the official end of college for you) by having a final visit with one of your best friends before she moves across the country.  Spend weeks anticipating the weekend, and then forget an important stack of clothes on your bed.  Nobody needs underwear, right?  Right.

Step 1: Accidentally drive THROUGH Chicago during rush-hour.
Bonus: Only have one anxiety attack.
Step 2: Arrive, and immediately be offered a glass of wine, eat the most delicious pizza with REAL, ENTIRE STRIPS OF BACON ON IT, and then sit outside by the fire pit with friend and her incredibly hospitable parents.

How To: Chicago | Candidly Kelsey

Step 3: Take the commuter train into the city the next morning.
Bonus: Ride the train for free because the conductor forgets to check/sell tickets.
Step 4: Take stereotypical tourist pictures.

How To: Chicago | Candidly Kelsey

Optional: Take somewhat confusing tourist picture. (It’s the Leaning Tower of Pisa Pose. Get it? Eh? Ehh?)

How To: Chicago | Candidly Kelsey

Step 5: Stop into Water Tower Place (mall?) when your feet begin to hurt, accidentally stumble upon a wine bar while looking for a coffee shop.  Oops?

How To: Chicago | Candidly Kelsey

Step 6: Return to place you are staying that evening, proceed to get ready for the Party Trolley.
Step 7: Party on said trolley, cruising the city while drinking vodka lemonades and yelling at pedestrians on street.  Don’t forget to stop and take a gorgeous picture of the skyline.

How To: Chicago | Candidly Kelsey

Optional: Pick up a pedestrian who just happens to be wearing a shirt that proved he went to your college.  Don’t ask any questions when he jumps on the back of the trolley.  Just roll with it.  It’s fine.
Step 8: Exit trolley.

How To: Chicago | Candidly Kelsey

Step 9: Let’s not talk about it.
Step 10: Leave city the next morning, return to suburbs.
Bonus: Leave your wallet, your favorite make up brush, and your dignity somewhere within the city.  Ask no questions, except “How do I cancel my credit cards?” and “What are the odds someone is going to steal my identity?”
Step 11: Enjoy final moments with one of your best friends before she moves many many hours away to start her big girl job.  Feel too broken from loss of pride (and license) to cry about missing her.
Step 12: Accept money from your friend’s amazingly gracious parents to help you get home.  Stop in NW Indiana to visit ex-roommate/other best friend for one day.
Step 13: Watch the Bachelorette Finale from her hot tub, and then sit around fire until 2am.  Try not to cry that college is officially over, summer is almost over, and real life is actually happening as friend discusses moving to law school.  Ignore the fact that you have no idea what you are doing with your life.
Step 14: Wake up entirely too early, and drive the last three hours home, still without wallet.
Bonus: Accidentally order $12.00 worth of fried chicken at a rest stop with precious, precious gas money.
Step 15: Shower off the last shred of embarrassment (and the chicken smell), and muster up the courage to go to a job interview.

How To: Chicago | Candidly Kelsey

Step 14: Rejoice. You are now gainfully employed as a waitress.
Step 15: Use your college diploma to soak up your tears while you go shop for black pants and non-stick shoes.  Tomorrow is the first day of training.

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