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Chicago Trip Recap

If you had asked me at the end of my last trip (out to Boston earlier this Spring) where the next one would be, I would have said “Well, I don’t know…I don’t have anything else planned!”. Somehow for me these trips always come up last minute or sort of spur of the moment. Even going to Italy in March wasn’t planned out more than a couple of months in advance! It just goes to show that you never really know what lies ahead. I had no plans to visit Chicago this year until a photographer friend, Libby, messaged me about an incredible deal on plane tickets that just seemed too good to pass up. Visiting Chicago together was fitting since we’d essentially met outside of it at a lakehouse photographer’s retreat called Turning Tides nearly two years ago!

I had no idea what to expect, but I do love food, so of course, lots of eating was on the agenda. We were only in Chicago for a few days, but managed to have a wonderful time! I am somewhat bummed though that I didn’t realize Lollapalooza was the weekend after we headed home because I’m dying to go to a music festival and that would have been so perfect! Dang it. Maybe next time! I took a mixture of dslr and iPhone photos while in Chicago. I wish I had taken more, but I’m glad I at least have a few! Just…don’t be prepared to see the world’s best photos as you continue through this post, but hopefully what this post lacks in prettiness, it will make up for in entertainment value and Chicago details 😉

The first night we met up with another friend, Laurie, who took us to Bridge House Tavern right on the river for dinner. I know this might sound ridiculous, but I honestly had no idea that Chicago had so much water surrounding it! Which, is kind of ironic to me since one of the biggest things it’s famous for is having been burned to the ground in a fire.

I really liked the ambiance at Bridge House Tavern AND the cocktails, but I can’t say that the food was all that great, though I did have a pork belly BLT, which you would think would be basically the most amazing sandwich of all time. It was good…just very plain tasting. But hey, if you like plain food, you might love this place!

The next morning we walked to the Doughnut Vault and then had breakfast at a random cafe nearby. I cannot say that I was super impressed by Doughnut Vault and I think it’s because we are SO spoiled here in Virginia with amazing donut options. Sugar Shack and Duck Donuts are pretty unbeatable in my opinion and Doughnut Vault doesn’t come close. BUT, it’s still way better than Dunkin, so if you’re in town and looking for a donut, totally check it out.

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After spending some time in the hotel room charging our phones we headed out to Millennium Park where we visited the famous Bean and walked around for a bit. We also decided to rent bikes (awesome decision) and ride them over to Navy Pier (meh). Riding bikes around the lake was so much fun! I really enjoyed it and wished we had explored more on our bikes. Navy Pier is very much like every other huge commercialized tourist trap in every other big city I’ve ever been to. I remember saying “Oh. I’ve been here before. In Baltimore. It’s called the Inner Harbor there”. Not really worth a visit in my opinion, unless you are into that sort of thing. Although, we did get Garrett’s Popcorn, which I hear is a thing, and it was pretty damn delicious. I recommend the mix of the caramel corn and the cheese corn. Legit.

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Before we left Navy Pier we decided to do the Architecture Boat Tour. A few people had suggested it and though I get seasick on almost any kind of boat (I get carsick sometimes even if I drive!) I popped a dramamine and went for it. This was SUCH a fun experience despite the heat feeling unbearable. There’s a bar and you can sit and day drink and enjoy the beautiful buildings and learn a little too. I would definitely do this again, but maybe at night.

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For dinner we met up with another friend, Lauren, and had dinner and drinks at RM Champagne Salon. The food was good and the drinks were wonderful! I had mussels, a zucchini and asparagus side with tzatziki sauce and a rose champagne (and then a champagne gin cocktail that was so good). This place was adorable and is definitely worth a visit if you love bubbles.

The next morning we went to breakfast out in Wicker Park at the Bongo Room. First, that neighborhood was the cutest neighborhood besides Old Town, where Second City is. Second, I had a sandwich there that was almost as big as my head! Holy cow it was so good!! Definite yes in my book. I love breakfast foods, so this meal made me really happy.

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We walked over to another donut spot after breakfast, Glazed and Infused. I only got about a bite of my donut in before leaving it in Nicole’s car, so while I say that I liked it better than Doughnut Vault, I can’t give it much more of a review since I basically didn’t eat much of it. But, if you are thinking about doing a donut crawl of the city, this would be a great place to visit since there’s another donut shop literally right across the street. Regrettably, there are no photographs of this since I left my donut in a car all day.

After this, we rode around town a little bit and then went to the beach. It’s not exactly like the beach that we have here, but it was still very cool to see. That was my first time visiting a Great Lake! We walked along the beach and then went to this kind of dive-y, cheesy, but still fun place called Castaways and had frozen drinks. It was really hot, you guys. These drinks were so necessary! Again no photos. It was hot and my phone was about to die.

Once we finished up there we drove over to the Second City for their walking tour. I was so excited about this because many of the comedians that I really love started their careers at Second City. I’ve read about it in a few people’s autobiographies, so it was fun to actually see it in person! The tour itself was really enjoyable and a nice way to spend the afternoon.

For dinner Wednesday night we were treated to the most amazing meal at the Purple Pig. One of our friends from the Turning Tides Retreat, Angelica’s brother is actually the chef there! The food is tapas style and it is seriously the most legit food I had the entire time we were there and is probably one of the very best meals I’ve had in my life. I loved everything I ate, even things I normally am just not all that in love with, like calamari. I also tried duck for the first time! I try new things every time I’m with these girls…at the retreat I tried swimming for the first time, and this year I tried a whole new animal. What are they going to get me into next??? Ha!!!

Seriously though, this was such a highlight of the trip for me! We walked back to our hotel after dinner and enjoyed the beautiful city skyline one last time before heading home the next morning. Such a perfect way to end the trip!

I can’t end this post without talking about our hotel, theWit Doubletree. We looked into doing AirbnB, but thanks to shooting weddings all over multiple weekends out of the year, I’m a Hilton Honors member, so it was more convenient to stay in a hotel, AND I could earn points towards future stays with them. I am REALLY glad we did this because the hotel was so close to everything. The train was literally right outside of our door. Being so central since we were visiting for a short time was wonderful!

All in all, I’m so glad I went! It was fun to get out of town for a few days and explore another city a bit. I liked Chicago a lot and I’m sure I will be back one day soon! Til then I’m looking forward to our last three trips of the year…Atlantic City, Florida, AND we saved the best for last….HAWAII!

Be sure to head back here tomorrow for a Baltimore wedding!

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