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Chicago in the Summer of 2020

This past August, I headed downtown Chicago with one thought in mind- adventure! Having parked before behind “The Bean” in Millennium Park before with the family, I was happy to remember where it was again. Chicago is a bit much for me to drive, even with all of my experience across the U.S., big cities still make me nervous. So when I can remember something from before and get to it and be done, I am one happy gal!


Now, I just wanted to wander and enjoy- no plans, no schedule, just go. So once again with mask in hand, sanitizer a plenty in my bag, I began around the Park. The “Bean” had strict entrances and exits, no dogs allowed, and the infamous pics you get in front of the “Bean” are a good 20 feet out now, due to fencing and Covid.  Maybe with a REALLY good selfie stick you can get a good pic, but otherwise it was a game of “Where’s Waldo?”


My stomach was talking and I figured I would just eat wherever the day took me, and it took me across the street to a Panera. LOL Yeah, real exciting, but it was familiar, open, and had seating available. Maybe it’s the Disney kid in me, but I am so used to scouting out a table every time I want to eat, that now I do it everywhere, especially now with Covid cutting the availability in half or more.  With my half salad and half soup, I enjoyed my Chicago view as I nestled into my booth with a smile of excitement for what was to come.


With a full belly I headed to a Souvenir shop where I bought my “Save Ferris” shirt because I had done the Ferris tour around Illinois and it just seemed fitting to celebrate it with the Tee. Happy I could shove it in my Loungefly, I skipped hands free to my next destination. I had read that the starting point for “Route 66” was around the block- amazing!! So a selfie done, check and check, and it was time to walk through the Loop area, the Riverwalk, and them some light shopping on Michigan Avenue.


The day was a beautiful 70 degrees, zero humidity with the sun shining above. My skin was warm to the touch, my smile huge with magic. I felt the City was made for me that day, and if I had a hat, I would have tossed it in the air in celebration. Even with some areas boarded up, police out in large numbers, I felt safe and made the best out of it.  Yes, the World wasn’t what I would like it at the time, but you have to get up every day and plaster that smile on your face, whether you like it or not.



I was looking for the Disney Store, as I had had THE most amazing moment there the last time I had visited.  We had one a spot to meet Jessie, or Joan Cusack, as she was having a meet and greet selling a new cowgirl doll. My youngest daughter, Emily, had taken her Jessie doll to every surgery during her Cancer treatments, so she was a big deal in our household. So when we got to meet her and she said “Emily” to our daughter (JUST LIKE IN TOY STORY!) it made us all cry. We even made the news that day- it was great!  (Check out the amazing moment on YouTube) Anyways, walking through those doors again of such a special Disney Store to me and my family, it was almost overwhelming since I was there alone. I enjoyed the Store, I enjoyed the shopping, but I missed my family dearly and could almost see our ghosts meeting Joan as I walked around. It was sad and magical all at the same time. But not sad enough that I didn’t buy something- got the Jungle Cruise Pop and the Chicago Disney shirt. I will be making a seperate post of Disney Store pics – keep an eye out for that!


After lots of walking up and down Michigan, checking out the Ducks, the architecture, the old Churches, exploring Macys, and historical buildings, I was once again famished!  Saw a sign for “Billy Goat Tavern” and thought “Heck, why not?”  I needed to have an official Chicago dog anyways and this sounded interesting. Walking below Michigan was really cool, a whole other city down below. Thankfully the Tavern was open and I ordered up my Chicago dog and enjoyed a quiet sit while I looked around at all of their history and memorabilia- even got a free hat on the way out. See all my pictures and the story behind this amazing place coming up this week.


It was an amazing day, the crowds were small, everyone wore their masks and it was a wonderful adventure- enjoy all the pictures!


Thanks for your support!

Going from “What If? to “Why Not” is my life motto and I work hard at living that every day. I share everything from moving to Florida to live near Disney World to road trips across the States. I love the cool, quirky, and crazy stuff that I can find on my Adventures, and every dollar you donate helps support my efforts and hard work. Thank you to ALL who support me!

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