Chicago, Illinois

Warning: this post is going to contain a lot of food descriptions. You will get hungry.

After many long hours of driving and sooooo many miles logged into our trip total, we finally pulled up to the home of one of Eli’s coworkers, Pete. He and his wife, Rachel, graciously invited us into their home and hosted us for our next grand adventure:

Chicago, Illinois

Chicago Skyline

I must say, this city has been my favorite so far. Seattle is definitely a strong contender but we have had such an amazing time in Chicago that I have to admit to the fact that it has stolen my heart. It’s possible that the winters there might actually kill me with the freezing temperatures and wind but these past few days have been filled with cool, breezy weather so walking all day among the skyscrapers has been relatively pleasant.

Since we have been on the road, we have faced the issue of receiving mail that we need and the only solution that we have come across was having things mailed to friend’s and family’s houses, which is what we did this week. Eli took advantage of Amazon’s Prime Day and ordered us a cool little gadget that would allow us to heat up leftovers and even cook in the van without consuming too much power. It’s a neat little device that looks like a lunch box that you plug in, throw all your food in, and zip up. It takes hours for it to cook things thoroughly but if you can plan ahead and get your dinner started in the morning, you’ll have dinner hot and ready for you by the evening, much like a crock pot. He also ordered a food product that he has been coveting for ages. If you’ve spoken to him in the past two months, I’m sure you’ve heard about his obsession with Soylent, a complete meal powder packed with all the nutrients your body needs. It’s like a protein powder on steroids and the company claims that their products are vegan so I’m almost convinced that this is only a nod at Soylent Green and isn’t secretly made with people. We tried it and it tastes like plain oatmeal and isn’t at all palatable unless you mix Ovalteen in it, but it is very filling so it works well as the meal replacement that it is intended to be. So, that was exciting.

Friday was our first full day in the area and it was mostly spent working. We did catch a minute for a lunch break, though, and Pete recommended we take a stroll down to Kauffmans, the closest that Illinois gets to an authentic New York bagel. Now, to be honest, I don’t think I’ve ever had a New York bagel so I can’t give an accurate comparison but I will say, it was quite delicious. We ended up also getting dessert there on Sunday and it was phenomenal. The theme of the weekend had been family style sharing so we decided on four desserts to split; a lemon bar, a caramel apple tart, a caramel brownie, and a strawberry cheesecake square. Normally, I would rank the desserts by flavor and eat from least favorite to favorite but in this situation they were all so good that I couldn’t decide.

We had been very strategic in our planning and got ourselves out of dull stretch of nothing in between Mount Rushmore and the city just in time to celebrate one whole year as a couple in Chicago. In between bagel runs and work, I planned out the night for us so that we could have a fun date night in the city. That evening we embarked on the train and headed to our first stop, Buckingham Fountain. From there, we walked along Lake Michigan, making our way towards the next destination, only taking one short detour to see and photograph The Bean, one of Chicago’s biggest attractions.


After about two long hours of wandering and waiting, we finally got to our dinner destination (which I had been ranting and raving about all day), Eataly Chicago. For those of you that don’t know, Eataly is a widely popular Italian restaurant/ grocery/ cooking accessory store in New York City and, as of recently, Chicago. My plan was to take Eli there when we eventually got to Manhattan and was pleasantly surprised to find one much closer to our current location, especially on our anniversary. This location was a slightly smaller than the senior of the two but it still had all of the food-porn goodness; beautiful, crusty breads, colorful vegetables, house made pastas of every shape, and cheese as far as the eye could see. We arrived an hour before our reservation and it was a painful experience being around so much incredible food when we were already so hungry. It proved to be too difficult for us. We caved and bought a cookie which, of course, was ridiculously good. After being seated, we decided on two different types of ravioli, mine being a traditional cheese and spinach with red sauce, and Eli’s being a bit more unique with purple pasta filled with pork shoulder, truffles, and the most incredible cream sauce ever. It was everything that I wanted Eli’s Eataly experience to be and even though I couldn’t try his pasta, he graciously gave me a bunch of his truffles, which I inhaled. I had never tried truffles before but now I am convinced that they are the best food in the world.

After our incredible dinner, we burned off all of the pasta on our two mile trek to iO Theater where I had gotten us tickets to see The Improvised Shakespeare Company. We had been intending on finding an improv show to go to for a while so we decided that this would be the perfect opportunity, especially after reading the awesome reviews. And those reviews were not lying. Each show is completely unique with no planning involved so, as they said, we got to see the first and last showing of this particular performance. The story is based off of a suggestion from the audience, so for this one in particular, we got to hear the rousing tale of “Mom Jeans” told in a modernized Shakespeare prose. At first, I was a little worried that it was going to be a sub-par but I was immediately proven wrong. The actors were so clever and hilarious, I don’t think I stopped laughing once the entire time. We left at the end of the night with sore cheeks. It was so impressive too, seeing them create an entire story out of a two word suggestion, keep the audience laughing nonstop, coming up with rhyming lines, and maintain running gags throughout the whole show. Improv is no easy task, it’s basically a superpower.

The whole night was amazing. The food was perfect, the show was incredible, and I shared it with my favorite person. It was all very romantic and it really made me stop and appreciate just how fortunate I am to be able to have all of these new and amazing experiences. I know I wouldn’t be doing this if it wasn’t for Eli and I am so thankful to have him in my life to share these adventures with.

Anyway, enough with the cutesy romance stuff. Day two we got to enjoy with our wonderful hosts. They took us all over the city, keeping us walking for a good seven and a half miles. It all started in my new favorite restaurant, Monteverde. If you go to Chicago, GO TO THIS RESTAURANT. It’s Italian “family style” dishes (and I say family style very loosely) that are pretty small but meant for sharing. The waitress told us that it is best to order seven plates between four people and share them but we opted for five dishes with a dessert and it was the perfect amount of food. Everyone was able to get a small serving from each plate. Our complete list consisted of fried tomato rice balls, fried egg with polenta and broccoli, gnocchetti with pesto, scrambled egg fonduta with avocado toast, spaghetti pomodoro, and butterscotch creme brule. Every time we tried something the general consensus was “Oh my god.” Everything was the best thing I have ever tasted; the seasonings were impeccable, the flavor combinations were spot on, and it was all prepared perfectly. I always thought the super fancy restaurants with overpriced small portions were a waste of money but after this experience, I am singing a different tune. We got the perfect amount of each food and were excited for each new thing they brought out to us. In all seriousness, I think I want to be buried in their gnocchi, it was that good. I highly recommend it if you have the chance to go, just be prepared to spend a pretty penny.

From there we walked to Navy Pier to ride the new Ferris Wheel, which was great but we did have to share our little pod with some strangers, since they seat eight and we only had four. We got some great pictures of the Chicago skyline and then went on to walk through the rest of the area and then on to the John Hancock building. One of the most popular (and most highly Instagrammed) spots in Chicago is the Skydeck in Sears Tower, where you get to stand in a plexiglass box with thirty strangers over 103 stories for the small fortune of $35 a person. We opted for the next best thing, 360 Chicago and Tilt. After paying $20, we went up 94 stories to the John Hancock building observatory, where you get amazing 360 views of the city. We ended up getting there at sunset and it was so exciting to be able to get that kind of bird’s eye view. They offered all kinds of cocktails and snacks and such so you could relax and enjoy the view but we were there for one thing and one thing only, to do Tilt. So, instead of standing in that plexiglass box over the city, Tilt consists of standing on a hydraulic, steel framed platform that slowly leans you outwards about fifty inches so that you are leaning out over the side of the building. You have the option of holding on to hand rails as you are lowered to certain doom, or for those of us who don’t feel fear or mortality (Eli), you can lay directly on the glass and hope that you don’t experience the first technical error to occur on this attraction.

Walking up to the platform, I was shaking. I think I was about two seconds away from chickening out, which is a very alien feeling for me, I feel like I’m pretty brave most of the time. Looking down to the ant sized cars driving below us just gave me an incredible sense of dizzying dread, but I did it. The operators lean you out and back in a total of three times, and I am proud to say, during the second one I laid on the glass, much to the dismay of my sweaty palms and quivering knees. Go me. So brave. I will admit, once you are actually leaning out and staring death in the face, it’s not as scary. You begin to rationalize the fact that if you do end up catching Tilt on a rather unlucky day, at least you would die instantly upon hitting the ground. Have I sold it for you yet? Honestly, it’s very thrilling and you get some mad bragging rights and a huge sense of accomplishment if you actually do it. I may have been terrified but I definitely think it was worth it and I’m glad I got to experience it.

Chicago Tilt

Chicago Tilt. Picture credit to A Dangerous Business Travel Blog.

So, after narrowly avoiding sh!tting our collective pants, our gracious hosts took us to another famous Chicago attraction, Giordano’s Pizza. I had told them earlier that I had a small list of things that I really wanted to experience while we were visiting and the biggest one was traditional Chicago pizza (I’m a foodie and I’m proud). So, once we ordered, we endured the painful, hour long wait for our pizza to be made. Why did it take so long, you ask? Well, partially because it’s a very popular place so it gets a bit busy, but it’s mostly because their famous pizzas are about four inches of double layered goodness and take a while to cook. That’s right, it’s a pizza with another pizza on top. Typically, a normal person will eat two to three slices of regular pizza but here it is close to impossible, no matter how badly you want to grab seconds. My tip would be to only go here if you have nothing to do afterwards though because you will go into a food coma. There’s no avoiding it but it’s so worth it.

So, we went back to Pete’s house and crashed hard that night and woke up super late the next morning with the intention of going out to experience more of the Windy City but seriously lacked the motivation. Instead, we lounged for a day. Eli got to play video games with Pete and Rachel and I blogged while binging some Food Network shows and cuddling their precious dog, Charlie. It was a well deserved relaxing ending to the weekend after the ten or so miles that we ended up walking in those two days. We are now fully rested, back to work, and continuing on our journey as we enjoy the pleasant weather of Michigan from a local cafe. So, as always, everything is good, everything is wonderful, everything is fine.


2 thoughts on “Chicago, Illinois

  1. You mentioned you wouldn’t be doing this if it wasn’t for Eli and that you are thankful to have him in your life. As his mom I feel I can say with certainty that he wouldn’t be doing this either if it wasn’t for you and that I am thankful for you being in his life. All mushiness aside, I think I will return to Chicago to sample more deliciousness!


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