About a month ago, I took a trip back home to Chi-Town. For those of you who don’t know, I was born and raised in the Chicago Suburbs (in a town called Naperville). It has been years since I went home and this time, I decided to take someone special with me.
A few realizations I made along the way:
- Driving into Naperville, I didn’t recognize a single thing until we were less than 2 miles from my home. Uhh.. Not sure if I was one of the least-observant children ever or if it has really changed that much?? But I was shocked at how little I remembered.
- It SNOWED our first day in Naperville. I was beyond excited! Our trip was 1 week after one of the worst Blizzards in Chicago history and there was only a 10% chance of snow the entire time we were there… Timing = perfection.
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Downtown Naperville Riverwalk
- I had my first ever drink of alcohol in Naperville (at the age of 24). Yes, I was one of those kids in high school. I was actually quite proud when Shawn pointed this out to me.
First drink = beer. Bar = Jimmy's. No brainer.- The museums are not nearly as entertaining as I remember. With that said, the dolphins, whales and sea lions (Aquarium) are still adorable and that will never change.
- The Billy Goat Tavern is one of the most entertaining restaurants... especially if there is a newbie in your group. (Look up the SNL skit)
- I have conquered a big fear of mine. After a few encouraging words (Read: big push), I did this:
This is the top of the Sears (Willis) Tower. Sherry and Shawn were not nearly as frightful.

- Portillos is still amazing. Italian beef sandwich, mmmm
- Shawn’s family = so much fun. Shawn’s mom Sherry, her boyfriend Jim, his cousin Erin and her husband Sean all came to Chicago with us. Traveling in a group can be one of the best experiences. We had an amazing few days with his family.
- Sherry, Erin and I pic:
- Boot shopping is stressful. Erin and I ended up with the same pair after a frustrating few hours on Michigan Ave. We decided there should be a way to ‘window shop’ from people’s outfits. Seriously, where do they all shop? Upside: good company :)
- We found a bar by Wrigley field, Sluggers, that has batting cages and arcade games. I would be in trouble if all bars were this fun.
- I no longer have my northern accent. Not sure how I feel about this. Especially since I don’t think I have a southern one either. Not sure where that puts me…
- I am much happier in cold weather. Yes, I realize I live in Houston and thus live in outrageous heat about 10 months of the year.
- My boyfriend is truly special. This trip was my birthday gift from him AND he gave me diamond earrings for V-day on our last night in Chicago! More importantly, I think how you travel with someone says a lot about a relationship...
and Shawn was the perfect travel buddy.
In summary, this vacation was the best. I highly recommend Chicago to anyone looking for a get-a-way.
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