Windy City Weekend!

Way back when I started working for my current company and found out they have a big office in Wisconsin, I had hoped to parlay a visit to that office with a side trip to see Anastasia. For being so close, and such a major city, it’s really expensive to fly to Chicago, and I haven’t been there much since she moved.

So, earlier this year when we began planning our work trip to Madison, I asked if I could fly home from Chicago and my company said yes! Woo hoo! I had been excited about this past weekend for months!

Last Friday afternoon, following a half day of work training and general team bonding, two of my coworkers and I drove our rental car to Chicago! The trip was a little bit of a never ending journey with traffic, rest stops, drink stops (my coworkers really like a good drink- I drove, so no drinks for me) and terrible construction around O’Hare. After almost 4 hours we finally made it to the Windy City.

From the airport, I hopped on the Blue Line, and Anastasia picked me up and drove me to her adorable apartment in Old Town. I wish I had taken more pictures, but the weather wasn’t really cooperating. The stop where I got off the “L” was Damen which was like a little Brooklyn. Seriously, while waiting for Anastasia, I was next to two hip, artisanal donut shops. Two! Anastasia and Justin’s apartment is adorable too. It’s a cute little brownstone with ivy growing all up the front steps and railings.

I was so excited to see my friend, and we spent the night eating pasta takeout, drinking wine and catching up. The best part of the night was when Anastasia asked me to be her matron of honor!! Of course I would!! She’s been my best friend since we met during our freshman year, and she made my wedding so special. I can’t wait to do the same for her.

Saturday morning, we were up on the early side and immediately headed to Starbucks for a little caffeine. From there, we ventured to the farmer’s market for some breakfast. I wish we could have hung out a bit, but it was raining pretty hard so we grabbed our food (savory crepes and croissants) and headed home to eat. We needed to fuel up for a big day of wedding dress shopping!!

After breakfast, we took the bus to Michigan Avenue where Anastasia had an appointment with J Crew bridal.the appointment was a little frustrating because many of the dresses Anastasia had requested to try on wee out of stock, which we didn’t find out until after she tried them. She tried on 4 or 5 really pretty dresses, and we both totally fell in love with one.


I’m not gonna go and and show the dress!

She really liked some dresses she’d seen online from BHLDN, but wasn’t able to get an appointment at their store while I was in town. We had some extra time and decided to walk in and see if they would take us. We lucked out big time because even though they were busy, they were able to squeeze us in between appointments. She tried on two dresses, but it was hard to get a great feel for them since the floor samples were in really rough shape. all their dresses are so interesting and beautiful, but I think she was leaning more towards J Crew after we left.


This whole day was so fun for me. I had never been to a bridal salon before my own wedding, and I gotta say, watching someone else try on dresses is definitely more fun!

After all that shopping, we were hungry again, so we headed back to Old Town, grabbed Justin and ventured to a local bar for some nachos and beer! They were so delicious. We shared a huge plate between the three of us and watched Rutgers get whomped by Ohio State. Ouch.

After our mini lunch we walked back to the apartment for some down time. Justin napped while Anastasia and I chatted and caught up some more. There’s nothing more relaxing than talking with old friends. We covered everything!

After some debate, we opted for Greek food for dinner and ventured over to The Athenian Room for steaks and drinks. It was really excellent.


After dinner, we walked home again. I can’t tell you how much I’ve missed city life. Walking everywhere, a million food options and tons of people everywhere. It was so fun to be in the heart of things again.

The next day we grabbed some bagels and coffee and just hung out before I had to head back to the airport. It was bittersweet coming home. I missed Chris and the pets a lot. I had been gone since Wednesday and was eager to get home, but I was sad to leave my friend. We had such a nice weekend exploring the city and wedding planning. I can’t wait to see both Anastasia and Justin soon!


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