A Surprise for 30

As promised from Monday’s post, we want to share more about my birthday weekend. Awhile back, Caitlin inquired about what I’d like to do for my birthday. I kind of brushed it off and said definitely not a party. She asked me a few more questions and left it alone. Some time passed and she asked if I could be booked for all day Saturday and Sunday. I checked my calendar and agreed, having no clue what the plan could be. Now try to keep up as you read this story from both of our point of views!

Caitlin

When you enter your late twenties planning a party is hard. And between Jenilee, Nick and I we are planners. And I don’t mean the actual planning is hard. I mean that we get so hyped up and excited about the people we love gathering around us. We look so forward to enjoying each others company. However, we have been burned by this excitement so many times in the past. I wasn’t willing to let people not showing up affect Jenilee’s big day. Cue the planning. With the dates locked in my mom and I began planning away.

Jenilee

Flash forward to Friday night. We had a great time at the Christmas Market, but made it an earlier night.  I was told I needed to be awake and ready by 7 a.m., so definitely need sleep! Luckily for me, Caitlin is super detail oriented.  While some would frantically be throwing everything they own in a bag to cover any eventualities,  I was able to avoid that! I received a picture of what she was wearing for the day, and then she told me yes or no when I sent her pictures of what I wanted to wear. I probably did a better job of packing than what I would do on my own!

Caitlin

We started first by deciding on Chicago to celebrate- so first things first, train tickets, check. We love taking the train to Chicago because you avoid any and all traffic and it is always on time. And you get to enjoy the entire ride relaxing. Our mom has stayed at the Kinzie Hotel previously with our dad and thought it would be a great choice for this weekend as well. We can confirm-she was right!  

Jenilee

We get in the car, and start heading towards Milwaukee. At this point I was imagining a fun day of walking around downtown. There is always lots to keep us occupied in our fair city! As we’re getting closer, my mom is asking if I need more coffee. I’m thinking – “heck yea – always!” and at the point we exited the freeway. My mom said, “ok I’ll grab the coffee and you park the car to Caitlin,” and I realized we were heading to the the Amtrak Station!

A that point, I didn’t want to make any assumptions, but my excitement was building. I asked where we were headed and they told me Chicago! My first reaction was disbelief and excitement. I love visiting Chicago, ever since our brother moved there. It’s been a city we haven’t explored much until recently, but now we can’t get enough of it. Plus, taking the train is the most ideal way to experience it! So we had a relaxing ride down there, enjoying our coffee and almond croissants.

Caitlin

I had discreetly tossed Jenilee’s bag in the car and we headed East toward this city. As we approached down-town my mom said well do you want to give her her first clue? Which is when she found out that we were hopping on the train! Our mom bee-lined it to Stone Creek Coffee, Jenilee got in line for the train (a must for my mom and I as we both get extremely motion sick and need to face forward), I parked the car and we all rendezvoused at the line. We enjoyed out coffee and pastries and sat back.

Once we got to the Union Station we grabbed a Lyft and headed to the hotel (which Jenilee still didn’t know about). Luckily our room was ready and we were able to check in early and unwind for a few minutes before we hit the ground running. So as you may have gathered by now I am a planner. Down to the minute usually, which can be a bit much sometimes. So we were choosy with what to pick for this trip in an effort to not overbook and then feel like we missed anything. So we played it at this point as if we were just going to do some shopping and kind of let the three of ourselves dictate the day. We maneuvered our way through toward the shops grabbed a fresh juice at Joe and the Juice and enjoyed our morning. Once I caught a glimpse at the time I said we needed to grab lunch and we picked the first place we saw called Wow Bao. It was a game time decision and delicious!

Jenilee

When we arrived in Chicago, I still didn’t know where we were headed for the day or anything! So we caught a Lyft from Union Station and made our way to the hotel, which was yet another exciting development for the day! We stayed at the Kinzie Hotel, which was a great spot and good walkability. So we were able to check in early and headed out right away to do some shopping! On our way we stopped for a quick juice to hold us over until lunch. I was feeling so grateful just to be down in Chicago for the day/night already, hanging with the women I love and having some leisurely girl time.

So we shopped for a couple of hours and found some great sale items. Then they wanted to grab lunch, and I’m always down for some food! We walked into the mall and grabbed some Orange Chicken Bowls to eat and they were eating pretty quickly so I figured something was up. We left the mall and my mom was basically running down the street back to our hotel so I was guessing we had plans of some sort!

Caitlin

At this point I silently started trucking it back to the hotel when Jenilee asked-are we in a rush? I said we’re not not in a rush and kept it moving. We dropped off our haul, grabbed a car and still kept her in the dark where we were going. We joked along the way that we were stopping at a fancy McDonald’s etc until we couldn’t lie anymore as the CIBC Theater lights flashed in our faces. I think this was the part my mom and I were most excited! We headed up, up, and up to our balcony seats and settled in. Hamilton was AMAZING. I highly recommend seeing this show if you have the chance. It blew us away how much they had to memorize between the singing and dancing. The theater is an amazing thing people.

Jenilee

We dropped off our bags at the hotel and grabbed another Lyft. As we’re riding in the Lyft, I had no clue where we could be headed. I was teasing my mom by looking at the address, even though it meant nothing to me. Once we turned on the street, I saw a sign up ahead and literally couldn’t not believe that it was where we were going. The CIBC Theater, and on the marquee said Hamilton. My mouth agape, I still was speechless when the Lyft driver confirmed that was where we were headed. I was out of my mind overjoyed and still basically speechless, but grinning at this point. We hopped in line and got in the theater and settled in our seats. This show is EVERYTHING people have hyped it up to be. I could not have enjoyed myself more and I am so thankful that my Mom and Caitlin wanted me to experience this masterpiece!

Caitlin

We took off after the show to get back to the Kinzie and enjoy their free happy hour! Yes, this did take part in choosing this hotel. We all grabbed a glass of wine, some snacks and enjoyed reminiscing on the show we just saw. We grabbed another glass and stopped back at our room to change into something a little more night friendly and told Jenilee we were going to grab burgers (one of her very favorite foods) at Au Cheval. I had been here with our brother and knew what we were in for so I was excited for them to try it. As expected there was a 3 hour wait so we put our name in and headed down the road.

Jenilee

We then headed back to the hotel, to partake in their happy hour. Free happy hour at a hotel is our love language with traveling and these two knew me so well. We were still high off the fabulous experience that was Hamilton, and enjoyed our wine and snacks. It was time to change and head to dinner, which they had told me was Au Cheval! I was super excited, because they know my burger loving heart.

This place has been on my list other times we’ve visited, and we knew there was going to be quite the wait. So we went and checked in, and with our three hour wait time settled, headed down the street. We knew of Bombobar through a blogging friend Lindsey, and their delectable looking confections were the perfect dessert before dinner! From there we bar hopped, because there were lots of fun options in the immediate vicinity. We hit up Lone Wolf, Punch Bowl Social, and The Emporium. They are all completely different bars but fun in their own ways!

We enjoyed our three hour wait, but were definitely ready for our burger. We walked in at 11 p.m. and ordered right away. This burger is all that it’s cracked up to be people! I loved and savored every bite I took. We rolled ourselves out of that restaurant and headed back to the hotel to sleep off our food comas. Wow, what an incredible first day!

Caitlin

One of our good blogging friend Lindsey runs the Instagram for a few restaurants in Chicago and has had us drooling over Bombobar for months so with our three hour wait in mind we decided we should probably get dessert first. It was delicious and I can’t wait to stop by again. From there we popped around a few bars: Lone Wolf, The Emporium and Punch Bowl Social. It was fun to again not really have a plan and just enjoy a new city. When my phone finally buzzed it was nearly 11 and we headed back to Au Cheval. At this point the burger was a lot to take down, but I am happy to say I did it. I overfilled myself and we all needed to promptly go to bed after dinner.

Jenilee

In the morning, we slept in a little bit and got packed up and checked out. We left our bags with the valet and headed to Wildberry for brunch. I’ve been here before and this is another spot that sees a lot of people come through, so get on their wait list. In the meantime, we strolled down the street and gazed at the Macy’s Christmas decorated windows.  It is totally worth the wait though, their food is fantastic across the board. We all ordered and shared our food with each other and they definitely don’t skimp on portion size either!

Caitlin

We were all movie a little bit slowly Sunday morning but got ourselves together and used Yelp to get in line at Wild Berry. We walked there and got to enjoy the Macy’s windows along the way which I have only done once before this so I loved it! We got to Wild Berry and of course as we waited we had to endure a family staring at us commenting on how tall we are. Sigh. Anyways we bounce back pretty easily from that and grabbed our table and promptly started drooling on the menu. Our mom and Jenilee split some omelettes and I can a Mexican skillet that was to die for and then I ordered the wild berry pancakes with it and they were equally as incredible. The food there was incredible and fed me for two days because the servings were so massive. I can’t wait to eat there again!

Jenilee

Feeling so full and thankful, we headed back out to finish off some more shopping. We perused Nordstrom Rack for shoes, which turned out to be great timing with the extra 30% off clearance. I found myself some black strappy sandals, that will be clutch for me in the summer and at $15, you can’t beat it! We were moving a little slower than we thought, so we took a Lyft over to , because Caitlin wanted to look at their winter gloves. After that, we were pretty much out of time, so we walked back to the hotel to make our way to the train.

After breakfast we needed to walk it off and did a little bit more shopping. We always spend much more time in stores than we intend to so the afternoon snuck up on us and we had to make our way back to the hotel to grab our bags and catch our train. We had another great train ride and once we got back we had to hit the ground running to make it to our basketball game.

Once we were settled on the train, it was such a relaxing trip back. Especially watching out the window, Chicago got hit with some snow, and I was super grateful none of us had to drive in that weather. We made it back in time for our basketball game by the skin of our necks and capped off a FREAKING AMAZING weekend with a win!

Caitlin

As one last perk our dad had come back earlier than usual from hunting due to the snowstorm we were anticipating so he picked up some pizza and we got to have dinner with our parents before going our separate ways for the weekend. All in all the weekend was a success! It is so hard for me to keep any surprises so I am so proud of myself for not ruining any of these ahead of time. It was so fun to watch the day unfold and spend this time with my sister and mom to celebrate Jenilee’s birthday. Our family has really converted into doing experiences as gifts rather than tangible items and we couldn’t love it more. Stay tuned for Nicks celebration (In March-hah!)

Jenilee

I can’t even believe they put all of that together for me, and I feel so utterly thankful, spoiled, and blessed. I felt so special and celebrated. It truly was the best birthday celebration I never could have planned for myself. I will never forget this weekend, so big big thank you to Caitlin and my Mom! I love you both!