Proud Big Sister: Downtown Chicago, IL

Many of you know that my husband and I grew up in the Chicagoland area and then moved away for college and jobs. We’ve been gone now for over 10 years but all of our family still lives in the same town so we go “home” several times a year to visit. This December we celebrated 10 years of marriage so while we were home for Christmas my hubby surprised me with an overnight trip to downtown Chicago so we could enjoy a kid free date night! Such a genius idea!! Like literally! We had so much fun just having time to ourselves, something we rarely get to enjoy, all the while rediscovering the magical city of Chicago.

We took Metra, a commuter train system that runs from the city out to the suburbs in every direction. There’s tons of these trains. Think of it like the cartoon Busy Town!


Once we got to the station I had to get my obligatory hot chocolate from Dunkin’ Donuts. I’ve done this since I was a little girl, no sense in breaking tradition at 33!2 3

This post may contain affiliate links, which means I’ll receive a commission if you purchase through my link, at no extra cost to you. Please read full disclosure here.

Our first stop was to visit my little brother at his work. He’s 7.5 years younger than me so our lives are totally opposite of each other. Growing up my sister and I babied the heck out of him and bent over backwards for him. We were the ultimate big sisters! So seeing my brother at his beautiful work made me such a proud sister – and of course, I’ll take all of the credit for him doing well. lol 🙂

gathered in the kitchen: downtown chicago



I’m the oldest in our family of 3. With that comes a lot of responsibility. Being the oldest you are always told that your siblings are watching and learning from you. Beyond that you are to take your younger siblings under your wings and help show them the way. Inevitably you feel somewhat responsible for how they turn out in life. You worry about them and hope that they will turn out just like you (hahaha just kidding!) Something that only all of you oldest siblings will understand.  🙂

Anyway enough sappiness…He works in the financial district of Chicago.

Downtown Chicago, IL

The inside of his building is like a museum. It’s so gorgeous! This is definitely something I miss about living back up north.

Downtown Chicago, ILDowntown Chicago, ILDowntown Chicago, ILDowntown Chicago, IL Downtown Chicago, IL

Downtown Chicago, IL

Downtown Chicago, IL

Downtown Chicago, IL



We then walked to lunch at a delicious Greek restaurant around the block.

Downtown Chicago, IL

Check out those racks of lamb behind the counter, definitely not something you see down here in North Carolina! I ordered one of my favorite Greek dishes, Spanakopita.

Downtown Chicago, IL : Spanakopita

My brother introduced us to Greek Fries! They were so delicious and I don’t really like french fries!! Downtown Chicago, IL

Fries, feta cheese, oregano and lemons. Literally they were amazing!
Downtown Chicago, IL: Greek French Fries

Clayton got a loaded Gyro. Downtown Chicago, IL: Greek Gyro

It’s hard to see in this picture below but that pinkish-tan thing is actually the rail track for the L-Train, a train system that rides above ground level (see the cars below?) Downtown Chicago, IL

We had so much fun and I have to admit, I’m kind of jealous that my brother is living it up city style for a bit! But glad my widdle bitty brudder has done so well and has as cool place for his favorite big sister to come visit! 🙂

We then walked him back to work and headed to our next adventure!

Downtown Chicago, IL

See Part Two: Water Tower Place (and more) HERE!



Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.