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Chicago & Madison


June 3, 2016


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Recently, my boyfriend and I went on a trip to Madison, Wisconsin and Chicago. It was one of the best vacations I have been on. I had never been to the mid-west and now I want to go back. The cities were beautiful! Madison was adorable with old homes and lake views on both side of the city. I was in photo heaven. I took over 700 photos on just my phone in the first two and a half days of our vacation. We were there for six.

We arrived in Madison on Monday afternoon. We met up with one of Adam’s friends from back when he used to live there. We walked State Street and ended up having lunch at Parthenon’s and had the most delicious gyro I have ever had in my life and am still craving. After lunch we headed up State Street and walked around the State Capitol building. After the capitol we went to check into our bed and breakfast that was right on the lake. This building was adorable and so charming! Our room was wonderful with a private bathroom with a whirlpool tub and a private deck facing the lake. That night we met up with Adam’s family and we had fun wonderful dinner at a little Italian place that also faced the lake. We ended our first night in Madison with some wine on our private deck.

 Front steps of the Capitol Building

Front steps of the Capitol Building


The next day in Madison, we woke up early and hit the road to Devil’s Lake. It was a gray, rainy, and chilly day so when we arrived there was only one other car there. It was gorgeous. I had never been to a place that was so rocky yet so full of trees. The lake is in a bowl that is surrounded by glacier rock and tree lines. You can climb to the top of the rock and overlook the lake. I was pretty adamant about not climbing the slippery granite in the rain but Adam talked me into and I am so glad he did. It took us maybe 45 minutes to climb to the top and I feel like that is giving me some credit. We had to stop a couple times so the very in active one of us could catch her breath! When we finally made it to the top, the view was unbelievable. I couldn’t believe how high we were. The lake was gorgeous even though it was a gray day. This was one of my favorites from the whole vacation.

 Our last day in Madison, we packed up or things to check out of the bed and breakfast and headed down a few blocks to Monty’s Blue Plate Diner. This was and I kid you not the first time I had seen a diner like they have in the movies in real life and I was in love. Everything was blue and white the food was amazing and the ambience was like a dream come true for me. l wanted to have my own little photoshoot in there like I had always dreamed of doing! After Monty’s we walked up and down State some more stopping in some shops and into a store called The Jazz Man in which to my surprise Adam has known the owners for at least ten years. They caught up some while Phil and I shopped around some. After our shopping was done we headed to just outside of town to visit Phil’s client, Isabel. This woman was the sweetest lady I have come across. Isabel lives in an independent living center and had Phil come to keep her company and help her around the house with whatever she needed to get done. Isabel and Adam immediately clicked. Phil says it’s because they’re both Sagittarius and I believe it to be true. She was so sweet and showed us the handmade quilts that she had made and photos of her family that she had out. Isabel was so sweet. After we visited Isabel we hit the road again to dive up to Elkhorn where Adam’s dad and his wife, Connie live. We stayed and chatted for a while and then started the drive to Chicago!


Arriving in Chicago was great. The only other time that I had seen such tall sky scrapers and in the amount that they were there was in New York City and Adam kept telling me that if I liked New York, then I would absolutely love Chicago. He was right. The buildings, the food, the culture, the walking! It was like heaven on earth! The first night we got there we checked into our hotel and we wanted pizza. So where do you go in Chicago for a deep dish Chicago style pizza? Giordano’s of course! The pizza was so good oh my goodness. And the caprese salad we had before, so delicious. Finally seeing first hand a deep dish Chicago pizza I understand why they call pizza a pizza pie.


The next day in Chicago we went to Art Institute of Chicago which was the best thing of the whole trip, in my opinion. We got to see famous paintings including “Nighthawks” by Edward Hopper, “The Old Guitarist” by Pablo Picasso and many works of Vincent van Gogh including all three versions of “The Bedroom” together for the first time in North America.  We spent pretty much all day and decided to go to Portillo’s for dinner. Oh. My. Goodness. I have never in my life had a sandwich that was as delicious as the Italian Beef at Portillo’s. This sandwich, which I ordered “extra wet” was carefully assembled starting with a French roll, then topped with special spiced sliced Italian beef that has been dipped in a wonderfully delicious au jus and then placed in the roll, topped off with sweet or spicy peppers, and more au jus. BEST THING EVER. Also, while I was writing about this heavenly food I found out you can have it delivered. 8 disassembled sandwiches shipped to your doorstep for $79.99. It just made my day.

 This was THE BEST sandwich I have ever had.

This was THE BEST sandwich I have ever had.

Adam and I woke up early and we had a nice breakfast in the restaurant of the Omni on Michigan Avenue. The walk there was gorgeous. It was overcast and chilly with the clouds rolling through the city. After breakfast we walked around town with Phil for a while and then we parted ways as Phil had to go back to Madison. Adam and I kept walking to get to the aquarium before they closed. I had so much fun! We saw otters, beluga whales, tree frogs, starfish and so much more! I touched a sturgeon which was weird for me. I saw jelly fish, and coral and seahorses. It was so gorgeous to see all these amazing creatures that we don’t see every day. After the aquarium, we walked so far to get to the Sears Tower to go out onto the glass ledge. I was so nervous. Adam found it amusing at how nervous I was, thanks love. We went into the elevator and went up 103 stories in 60 seconds. That’s 1600 feet in one minute. We got to the top and I did it. I did the sky deck. We stood in the glass box that hangs on the side of the building, 1600 feet up over the city. It was amazing.


After the Sears tower, we went to dinner at Ditka’s Steakhouse. I had the best cocktail I think I have ever had. The Raspberry Smash Martini was heavenly. The food was awesome, the ambience was wonderful even though I am not a sports fan what so ever. After dinner we went to the top of the Hancock Building and overlooked the city with all its like in the dark sky. Beautiful. After the Hancock tower we went back to Ditka’s for more drinks and then headed to the hotel where we met a wonderful fun woman named Suzy.

Suzy was awesome. Black leather jacket, perfect white hair in a short cut. We hit it off with her almost immediately. We sat in the hotel lobby bar talking with Suzy about Chicago, Austin, love and life. The three of us sat and talked for nearly two hours. Suzy is, in my opinion, the most interesting woman I have met in my life. 

The next morning was our last day in the city and we had two more stops to make. Garrets popcorn, (of course) and Eataly. We walked round, went in and out of tourist stores to get things for my family. We stopped in stores on Michigan Ave and looked and loved and I can’t believe I had enough self-control to not buy the $60 trench coat I fell in love with. We ended up in Eataly and I was so happy. Maggie told me we had to go when we were there and I am so glad she told us about it. Eataly is a two story building with 9 restaurants a massive market area that sells only and all Italian products. The wine section, Oh my god the wine section, was HUGE. After we ate at Eataly we headed to Garrett’s popcorn and I didn’t know that popcorn could be so good in my whole life. We headed back to the hotel and packed up everything to head home. I was so sad. I wanted to come home, grab the dogs and go back.

I loved every minute I spent on this vacation. I would love to go back one day soon and explore the city a little more. Eat more food, especially Portillo’s beef sandwich, and Ditka’s again for that amazing martini. Thank you, Adam for taking me to a great city. I loved it!







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