36 Hours in Chicago

The story of how this trip came about follows the itinerary. I understand that most people come to my blog for travel tips and the itinerary for ideas to recreate, not for my personal development stories that initiated these trips.

Sometimes the best memories are created on a whim, created in a short time frame, and with little expectations. Life happens whether or not we are ready, so why not be a part of it, instead of being a bystander?  Not in just traveling, but in all we do. 2019 is about being present in the moment, appreciating it while it’s happening and not taking it for granted, and to give back because nothing is worth while if we aren’t sharing.

Transportation To/From:

Car. Living in Ann Arbor Michigan this drive is really quite easy, 3/12 hours on I-94 to Chicago. This car trip is especially good if you have a good audio book in cue, podcast, or someone awesome to share stories with and talk to.

Transportation Costs Roundtrip:

Gas: $80

Tolls (if taking the express route): $25

Parking: Used the Spot Hero app: $60 for the weekend Friday-Sunday


Warwick Allerton 

Cost: $85/night

This hotel is a classic beauty. It’s an older building from the outside that has underwent a massive uplift inside. You walk into the doors and gave the vibe of money and ritz. Everything in gold and white, everyone greeting and opening doors with a smile, and assistant to the elevator that led to my anxiety; as if the welcome at the door didn’t do that enough. All in all the hotel was clean, the staff was hospital, and the location to downtown was perfect; if plays and the Magnificent Mile is the purpose of your trip.

screen shot 2019-01-14 at 8.26.21 pm

Day 1:  

  • Drive after work to Chicago (Arrive Around 10pm)
  • Checked in to Warwick Allerton 
  • Walked toward Broadway Downtown Chicago
  • Walked in search of clam chowder, stopped in at Fisk & Co


Day 2: 

  • Walked to the Lincoln Park Zoo (free admission)
  • Went to The Diag Bar to watch the Michigan football game (arrive VERY early for a seat)
  • Get ready for a play at The Allerton
  • Walk to the CIBC Theatre to see Hamilton
    • Cost for a Saturday show $170

Hamilton ChicagoDay 3: 

This trip to Chicago was a complete surprise… well kind of. I will share.

Disclamer: Before sharing, my blog site is like Planet Fitness, a judgement-free zone. It is my story, intended for to share my experiences for personal documentation too.

The end of September I asked the universe to listen to and help provide me guidance on my journey. I was at a point where everything seemed to be aligning perfectly. Work was becoming natural, my traveling had been on an all time high, family relationships were being resealed, my commitment with friends had never been better and I was at peace with my personal goals and development. The only thing missing was a genuine long-lasting connection, a relationship.

I signed up for Bumble.

Quite quickly my prayers were answered. I matched with someone and was well on my way on my first date with someone on the dating app. After a couple dates with him, this trip was suggested and quickly planned. Surprisingly, this is the first trip, ever, that I was planned 100% not.by. me. Our natural connection surely paved the path for some stops on this trip that were not planned… the zoo, Fisk & Co, and Grand Lux Cafe… but each cementing something meaningful and unlike anything I’ve felt before. This trip proved to me to trust my gut, trust my heart… but most importantly to have faith and ask for guidance when needed.




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