Sunny Times in Chicago


After making the move to New York, things are still a little hectic. Between not having an official place of my own, commuting to the city, immersing myself in awesome projects, and being separated from my little red mixer, I kind of don’t know how to deal. Its really tragic. Obviously the best thing to calm my nerves is escaping on adventures.

This time it took me to Chicago, a city I had never been to, and it was absolutely awesome. I’m not sure if you’ve caught on yet, but I’m currently dating this guy who is a little more than awesome. Unofficially, we’ve been together for 3 years, which is pretty cool. I can’t even make up my mind about what ice cream to have, so sticking with one guy really should be applauded. We aren’t exactly sure when our actual first date is, so we ball park it. It works. Lets just go with it. We like eating meat, so we went to Chicago to eat delicious meat, among other things. Overall an amazing way to spend the last official weekend of summer.


Architecture is unreal. I never get sick of it.

I had always heard such great things about Chicago but never made it the top of my list. Dear God, why not? Chicago is totally kickass. Delicious food (and not just deep dish pizza), sunny days, boats, buildings. Chicago has seriously got it going on. I’m pretty much a city-phile, so tall buildings and too many people always feels like home. The architecture is seriously redonk. I couldn’t stop looking up. Gorgeous buildings everywhere.

We were lucky to spend a few days with friends who lived in an awesome area and took us around Chicago (bike tour anyone) and introduced us to delicious food. I didn’t look up reviews once. At all. Oh except for chocolate cake. Essential. We had a Chicago experience from locals and then a little time to ourselves, which was absolutely perfect. I was pleasantly surprised by Chicago and I will definitely be back. Except only in the 4-month-long summer. I don’t like winter in New York, there is absolutely no way I can handle it in Chicago.


Beach, lake, and more buildings.

If you head to Chicago…DO THIS

  • We frequented awesome sports bars, a few lounges with delicious drinks, and were welcomed with a fantastic chorizo-benedict brunch by our foodie friends our first morning there. I am a huge fan of chorizo and Chi-Town. Here are a few specifics that I will definitely do again:
  • Wrigley Field – Got off the plane, went to a cubs game. Obviously. Cubs lost, and it was hot, but beer fixes that. And we sat near the greatest group of guys. Hecklers to everyone, especially the nearly-naked girls, opposing team fans, and just anyone in the vicinity.
  • The Peasantry – Awesome restaurant with the most interesting combination of flavors. Sweet potato pancakes with pineapple glaze. Trust me. Its amazing  And the best Bloody Mary I have ever had. And I hate Bloody Marys.
  • Lou Malnatis – When you think of Chicago you think of pizza and when you think of pizza, this is what you should be thinking. This was delicious AND they place a layer of meat on top of all the cheese. An entire layer. Yes, it’s incredible.
  • Portillos – This was the surprise of the weekend. The best chocolate cake (it’s known for it) that is not from a swanky restaurant. This is a hot dog-to-go kind of place and they cake was perfect. Just chocolatey and delicious. Nicely played, Chicago.
  • Bike Tour – If you want a nice overview of the city, this is the way to do it. Chicago is beautiful and each area has a different view of the city center. And riding along the water is cool too. We rented the Divvy Bikes and cruised our way around the city. Through Lincoln Park, Navy Pier, and over to Millenium Park to see Clouds Gate (The Bean) and Buckingham Fountain.
  • Chicago Riverwalk –  Underneath the main streets there is litterally a walk along the river. Its so peaceful and plenty of stops along the way to grab a snack or a drink. On a hot day you can even convince two non-wine drinking guys to polish off white wine.
  • Hancock Building – Of all the impressive buildings in Chicago, The Hancock is uberimpressive. Its huge and black and very ominous looking. And charges $18 to go to the observation deck. Don’t do that, instead pay $15 for a girly drink (or $10 for a gin & tonic) at the Signature Lounge on the 96th floor. We waited in line for about 5-10 minutes had a drink and enjoyed killer views. Seriously. This is a must for any trip to Chicago.





1 thought on “Sunny Times in Chicago

  1. If you keep writing these wonderful essays about Cape Cod, New York, Chicago, California Wine Country, the Rangers, the Cubs, etc., some magazine or TV show is going to start PAYING you to travel around and write for them!! Watch out. People are reading! Chocolate cake around the world!

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