Road Trip: Chicago

Chicago is one of my favorite city’s in the great US of A! In high school I worked for the trade association my Dad was CEO for (where I work in membership now) as a intern in their meetings department, the first onsite meeting I ever got to work was in Chicago. From that trip on I have loved this city and with family in Milwaukee, plus later career endeavors I have been back a few times and always loved it! In fact pre- Danny I was pretty sure I would move to Chicago after college. That of course did not happen- so instead I am always itching for a chance to visit.

Chicago July 2017

In 2012 my brother had just moved to Chi-town and was working for a hotel. A few times that year we tried to make a trip work – Dan even wrapped up a travel book for Christmas! But with health issues or the bills from health issues, it never worked out. Chicago was tossed in the pile of trips we just weren’t meant to make. So getting back there this summer was not only really exciting for a visit, but it again represented our new life: we aren’t just dreamers anymore we are doers.

Chicago July 2017

Over my many different visits to Chicago in the past it was often centered around the traditional attractions. We visited the Navy pier, we ate at Billy Goat Tavern, and we visited the Sears Tower. Or I was blessed enough to be on the Flaherty Family tour where I saw where my grandpa went to school and the house he lived in. These trips were always a lot of fun and gave me a great sense of this Midwest city: a place full of laid-back, friendly people who appreciate a good meal, a fun shop, or an exciting exhibit – but without some of the intensity to be chic as DC or New York. I really love this about Chicago and hoped Danny would experience that vibe too.

Chicago July 2017
Chicago July 2017
Chicago July 2017

So this stop we had just a few goals: stay in a fun hotel, visit some of the parks, take the architectural boat tour, and enjoy a nice dinner. Mostly we hoped to just sort of be absorbed into the city…. and that is exactly what we did…

Chicago July 2017

First stop The Palmer House Hilton. This beautiful, historic property has so much charm from the moment you walk through the door. Dan let me pick our place to stay for the night- Chicago has some awesome hotels- and even though I have stayed at The Palmer House before, it is so unique I reallly wanted Danny to experience it too. Plus I never felt like I had spent enough time taking in all the details. So we read all the plaques, drifted back in time with the traditional 1900 touches, and marveled at the incredibly beautiful murals….. which are best viewed (we think) from a stool at the bar – with Margarita in hand!

Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017

Our first night we took to the magnificent mile and just started walking. It was a little different than I had remembered and since shopping wasn’t on the agenda- both Dan and I felt a little frustrated to feel like we were just in Tysons Corner mall. So we hopped off the main drive and started to walk around the side streets …. and as luck would have it we stumbled across a cute Italian spot with the smell of fresh bread and rich spices wafting out onto the street. We grabbed a table…. welcomed the option of a big pour of Cab and ate until our hearts’ content. That dinner left me ready to crawl into bed…. but for Danny it was the opposite: he was energized. Once the check was signed we took to the street and just started walking….With each new beautiful church or postcard view we just became more and more excited to keep going and that night Danny fell a little in love with Chicago too!

Chicago July 2017

The next day we actually started out early with coffee in hand to hit the parks. We walked our way all over from the one side of Millenial Park to the other side by the river. Taking in both the famous sights, like the bean, to the locals spots like a few cute dog parks. It was the perfect way to experience the city – and what summer might feel like without the D.C. Heat!

Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017….Anyone spot the Chicago City Shiba Inu???

After walking so much, we enjoyed a boozy brunch and made our way to the thing I was most excited for: the Archtectural Boat Tour. I had taken this tour about 15 years ago and still remembered how awesome it was… so I talked Dan into it! It truly is the best way to get a feel for the city, learn some history, see some impressive buildings, and we LOVE any kind of boat. The one thing I had not recalled was the open bar…. probably cause it didn’t apply then 🙂 ….. but it certainly did this time and we loved it.

Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017
Chicago July 2017

I knew I would love our Chicago stop and I was pretty sure Danny would too. But as we drove, I was a little nervous that he might hit a wall and crash. When we arrived he did need a nap and I thought, well we have limited time but this will be fine! I can take a long shower, get a coffee, and blog! By the time I had unpacked a little and showered Dan was up and ready to roll. For a second I was almost frustrated…. “but, but I was gonna relax” I thought. That is what we normally do…. and then I remembered this is what we had been waiting for – Dan to not need a break and with that we took to the city streets. As we walked I was just walking truly overwhelmed with emotion. Here is my favorite date, with his go go go attitude that I had not really seen since our early years dating. With every new site we saw he became more animated …. pulling up maps of more places to go or heading to Google to learn a little history …. and for what trivia he couldn’t find out, he would just make it up- another favorite trait of mine, good stories with a side of dimples! We have come so very far and what if this is truly our new normal???

Chicago was a ball…. and we already have a list of things we plan to do next time! I am so tickled that Danny came to love this city as much as I did and that we both have admitted to pulling up Zillow just to look since visiting. In fact Danny liked it so much he opted to visit again when passing through alone for the end of the trip…stay tuned for a little Wrigley field action!

Thank you so much for reading and remember to make it a great day!
Jackie


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