2017 Chicago Pride
Planes, Trains, no Rental Cars and two Megabuses: How to escape Chicago during Pride Weekend Part One


This is a three part tale about how Chicago loves me and didn’t want me to leave her in 2017. My plan was to fly out of Cleveland, transfer in Detroit, arrive in Chicago, pick up a rental car and a former roommate and drive back home. Several things went wrong with that plan and, as usual, I learned some things about myself.

  1. My flight from Cleveland was delayed.
  2. My flight from Detroit was delayed.
  3. I arrived in Chicago expecting to drive away.
  4. My rental car reservation experienced a complete snafu beginning and ending with my misunderstanding of some rules and poor communication from the staff. 
  5. I was now stuck in the Chicago airport and needed to be on the road.

So, what’s a smart traveler to do? I called my former roommate for advice. I was told to take the Blue Line from the airport to someplace near her friend’s house then Uber to the apartment. We were going to take a Megabus to our next stop and pick up a new rental car because I HAD to leave Chicago. And this is where the next series of events went wrong.

I hadn’t seen her friend in a year so we sat and caught up. Then more friends came to the apartment and I got to know them. And my former roommate met the new friends. Then I noticed the time and thought we should get going. So we did.

BUT it was the Sunday of the Chicago Annual Pride Parade. 

So we hustled out of the apartment, down the street, to the train station and towards Canal Street. 

With two carryons and a back pack. 

With crowds of parade participants. Big crowds that flooded the train car and platforms and made it difficult to change trains. 

Then we had to load our CTA card, again.

At the final train exit, we realized we’d have to run to make the bus so we start running the few blocks to the bus stop. BUT I hadn’t run in over a year due to my plantar fasciitis and I had been self medicating with ice cream to address my grief. I was not in ANY shape to run especially with luggage. 

So, my former roommate ran ahead and around the corner to let the bus know we were coming and to delay it so I could hop on. I arrived several minutes later to see her look towards me and give me the thumbs down. 

We’d literally missed the bus. The Megabus.

Read what happened next in Part Two.