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October 27th 2019
Published: October 31st 2019
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Chicago was a city that I had always wanted to revisit. I went when I was 16 years old in a travel camp, but I didn't remember much from the trip. I was happy to discuss the trip with my friend Kenny and also visit Milwaukee. As the trip got closer, I had a lot going on with moving to North Carolina and starting a new job. I was able to push back the start date to the following Monday which gave me an extra day when I got home to finish packing and then drive down with my dad. I arrived at LaGuardia airport and noted how fascinating it was to see how the construction has evolved over time since my days of working at Terminal B. The TSA precheck line was decently long and took about 10-15 minutes to get through. I was a little disappointed with the amount of people that have signed up for it especially in New York since it makes getting through more of a hassle than when traveling in other cities where the line isn't as bad. I was able to switch my seat to an one seat emergency exit with tray stowed in the arm rest. It was very unique experience and hopefully will get another seat like this one day.

We sat on the plane and an announcement was made that we were going to be held for 3 hours due to weather conditions in Chicago, however it ended up only being an hour delay. As you approach the city, you see the water hitting the shore from Lake Michigan, as well as the city skyline and Wrigley Field. I was surprised how far the airport was from the shoreline when you approach the city. As we walked through the airport the terminal wasn't the most attractive to look at, but the size of it was impressive. I learned that the traffic enforcers do give out tickets to cars if they cut the line with picking up passengers which I thought was great and should be enforced in New York. It was very easy to get Lyft/Uber in the city and would definitely recommend it. It took 25-30 minutes to get to the Airbnb with some moderate traffic. We stayed in a coachouse which was a completely foreign term to me. It is a house in the back lot of another house in the front. It was a very residential area with detailed instructions to get in. There was a box with a key and a code given to us. We opened the box and used the key to get in then went upstairs and another set of keys was left in the place and the original key had to be put back into the box for the next guest. The coachouse was past a gate and it was a two story level home.

The kitchen had tea, utensils, plates and instant coffee. The bathroom had a cool looking circle shower and decent sized. My room did get pretty warm at night so I needed two fans to cool down, but otherwise it was a beautiful place. We took Lyft to Lincoln Park zoo. I would highly recommend this as it was free to get into the zoo. We ate RJ Grunts for lunch nearbye and it had old school photos on the wall. It was a quirky fun place to eat and walking distance to the zoo. We split two chicken sandwiches that came with homemade chips. One sandwich was like a French Dip and the other was a BBQ. They both were delicious and the chips was tasty. We walked to the zoo and saw so many different animals. We saw a wolf, snakes, gators, mongoose, rates, camels, red kangaroo, African apes, monkeys, lemurs, storks, hogs, vultures, zebras, penguins, fish and giraffes. I was amazed with the great selection of animals for a free zoo.

We walked to the Lincoln Park Conservatory and saw flowers and psychedelic artwork. This was also free and an easy walk from the zoo. We took a Lyft to go for the Architectural Night boat tour. On the way, you see huge buildings right along the water and the Ferris Wheel in the distance. There was a decent amount of traffic since it was around rush hour. We went to check in and there was some confusion as the 5pm boat we had booked online didn't exist, so we ended up on the 6pm. We had to kill some time so we walked to the Navy Pier. We saw the Shakespeare Theatre, Ferris Wheel, huge boats/helicopters to rent, beer garden, restaurants and a lot of shopping. The views of the city by the pier was surreal.

We went for the tour and saw the original skyscraper that was the first in Chicago. There was beautiful buildings along the Riverwalk with restaurants and bars. It was fascinating to learn the history especially on the Great Fire that occurred in 1871. We saw the Wills tower, which was originally called the Sears tower until 1996. There was high end coops and apartments in River North. The sky was beautiful with the buildings lit up as it approached night time. The tour guide was knowledgeable and funny. It was a 1.5 hour tour and definitely would recommend it. We walked to Pizzeria uno for dinner. It was originally established in 1943. We put in our name on a reservation and didn't have to wait too long to be called. We had a deep dish pizza with a lot of meat and peppers on it. It was the small pie with a semi flaky crust and not as heavy as I expected. We took a ride share back to the Airbnb and went to sleep.

We woke up the next morning and went to Wildberry Pancakes. I would recommend to put name on yelp list reservation of the day you are going. We had a 15-20 minutes wait and by the time we got there we barely waited at all. The place was beautiful walking inside and we sat upstairs overlooking the restaurant. I got a Harvest Skillet with 2 Cinnamon pumpkin spice pancakes. The food was ridiculously delicious and a huge portion with excellent coffee. We had a short walk to the MCU Contemporary art museum. There was a freedom of speech Virgil Abloh display. It was a cool thing to look at and he worked with various rappers, such as Kanye West and ASAP Rocky. There was designers sneakers, socks worth $90 and other works of art to check out. We walked down the Magnificent Mile along Michigan Avenue to see a Chicago Blackhawks team store and designer shops. We went to Millennium Park with the Famous Beam. It was cool to see, though somewhat crowded. There was a huge reflection pool with water coming down that would allow you to run underneath to cool off if it was too hot outside. We saw Grant Park with the famous fountain that goes off in the beginning of the show Married with Children.

We took a Lyft to Tortilleria y Taquerias for lunch. It had great tacos with an interesting variety to choose. I had goat, chorizo and tongue. It was a quick cheap food with a very authentic vibe to the restaurant. We walked into Little Italy and stopped at Coffee Alley for coffee. It had a good relaxing vibe in the shop. We took a ride share back to relax at the Airbnb. We went to Lottie's local bar for a drink before dinner then went to Club Lucky for Italian. You can make a reservation for the restaurant. It had good warm bread with olive oil to begin. We got eggplant parmigiana, calamari calabrese and side of veal meatballs. It was a tasty meal with good portion sizes to split for 2 people. We walked to Wicker Park Emporium. It had cool nostalgic arcade games like Tetris, Mortal Kombat and Simpsons along with different craft beers. It was funny to see how terrible I was at the games as an adult, but as a kid I was a lot better. We walked back to the Airbnb to rest.

We went to Flo for breakfast the next morning. It was a southwestern looking restaurant that you can make reservations. It had cool looking art on the wall and cactus items in front. I got this chorizo scramble with potatoes, beans with a fuego rojo sauce. The sauce was smokey and spicy. The coffee was delicious so I would recommend this place. We went to the Cubs game at Wrigley to walk around before the game against the Pirates. It was a cool looking stadium with many restaurants and bars close. There was rooftop seats on top of bars and apartments that you could pay for all you can eat and drink, however it was far away from the stadium to see. We got a Pedro Strop bobble head and went down first base line for batting practice. It was great to see Cubs and Pirates players up close. We sat in the 400's under the share and had great views of the stadium without the sun in our eyes. It had great views of buildings behind the stadium. I had a Chicago style hot dog that I did enjoy with onions, relish, tomatoes and mustard, which is a big contrast to the New York style hot dog. I also had some Giordanos pizza that had a much thicker crust than the one at Pizzeria Uno. We left in the bottom of the 7 with the Cubs winning 12-6.

We walked to Sheffield's for a drink near the stadium passing by so many restaurants and bars. We left for Air Bnb and relaxed. We went to dinner at Girl and the Goat. You need to make a reservation at least 2 months in advance and the time you will get won't be the best, but the food was so good. We had a blueberry cornbread, duck tongue, sugo pasta with beef/pork/goat, goat empanadas, confit goat belly and pig face. The Empanadas and cornbread especially were big highlights. We split a caramel corn and malt balls for dessert and would get that easily again. We went back after dinner since it was very late with the 9pm reservation and went to sleep.

We went to the rental car place and got a Elantra for our day trip to Milwaukee. We stopped at the post office to sell the two bobble heads and made some money since neither of us was keeping him since he wasn't a great player. On the drive we saw some shopping, pretty low key looking highway except for a random tank on the side of the road. There was a lot of construction ongoing on the drive. As you arrive into the city you see cool looking charming buildings. We stopped at Milwaukee public market which was 1.5 hours from where we stayed. It had a wide variety of shops and restaurants with a very happening lunch crowd. We went to St Paul's fish company for lunch. I got a walleye fry with fries that was so delicious. You can buy homemade chocolate or ice cream at Kehrs Candies. I got a pecan milk chocolate rectangular bar that was good. Anodyne coffee also is a big recommendation. There was a cheese shop that had samples of 6 year cheddar cheese that was tasty, though a big tough to chew.

We walked along riverwalk that differs a bit from San Antonio's but was cool to see. There was a Fonz statue with some gothic buildings within the city. It was very small city and quiet. We saw the Historic Third Ward. There was these lime green or black scooters to rent all over the city. We saw the Milwaukee Bucks stadium The highlight of the city was the Miller beer tour. It was very large and spread out. You start in the theatre and get to try Miller Lite beer. You walk into Miller Valley and the streets are so wide. We got to see the areas of fermentation, packing and shipping. It was the full effect to see how beer was made. We got to have Miller High Life beer in the Miller inn that resembled a German Brewhaus with stained glass and beer steins. There was caves that dated back to the 1849 that could be rented for parties. The tour guide was forceful, but nice and informative. We saw the packaging area that had stacks of beer similar to Costco or BJ's which I loved seeing. A machine can make 1400 bottles or 2000 cans in a minute. I got two cups of beer at the end of the tour so my choices was Leinkugel grapefruit shandy and crispin rose. The beer was pretty decent.

We went to Miller Park that was very different than Wrigley with not much nearby except the huge stadium. You can park on street with local business about 10 minutes away and walk to the stadium for free. There was Hank Aaron and Robin Yount statues outside. We went in and walked around the stadium. We saw San Diego Padres batting practice. In the stadium there was a batting range, playground, speed for running tracker and pitch speed. It was cool to see that if the Brewers hit a home run fireworks got off and the mascot Bernie goes down the slide. It was fun to see the Sausage race with the different characters live in person. I would recommend to wear something comforting in the fall because with the dome open it was pretty chilly. We left during the 7th inning to head to Swinging Door exchange in Milwaukee. It was a low key looking bar. I got a crunch chicken sandwich with caramelized brussel sprouts. It was a large sandwich and the sprouts was tasty. It took us 1.5 hours to get back to the Airbnb for sleep.

We got a quick breakfast at Dunkin Donuts and went to drop off the car at the rental car place at the airport. We dropped off the car and took a shuttle to the terminal. We got to the airport early and was able to switch to a flight 2 hours earlier than we were going to leave. It was kind of the Delta hostess to allow us to switch and not wait. It was a good flight with a slight delay, but we still got in earlier than we would have on the later flight. It was about a 20 minute delay. As I sat on the plane looking at the New York skyline I thought to myself it was surreal that I was going to be starting a new life in North Carolina in 2 days. Many thoughts through my brain occurred, but I was excited at the opportunity and very happy to have taken this trip before my new journey.


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