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ChicaGO is a MUST GO!

Updated: Mar 11, 2020

So as many of my followers know, Mike and I have decided to go on small weekend vacations to major cities every month or two. We decided to do this because we want to travel as much as we can, while we are young and can, but at the same time do things that don't break the bank and make us take off many days of work. For our first trip, we decided to go to Chicago from July 7-9. 

Why Chicago? 

Mike and I were inspired to make Chicago our first short trip when his friend went to Chicago not too long ago. He raved about the Chicago deep dish pizza so much that Mike actually ORDERED Chicago Deep Dish pizza FROM CHICAGO and had it delivered to us. As soon as we had our first bite, we knew we had to put Chicago at the top of our list.

Because Mike is a barber, he only gets off Sundays and Mondays, so we decided to work around that. We booked our flight for Saturday night out of Newark for 8:00pm. The flight was only 2 hours long and luckily for us, both our flights arriving and departing were right on time. Getting off at O'Hare International Airport, we were immediately greeted by our LYFT driver, who gave us awesome advice on where to eat and go. 

After our 20 minute drive to our hotel, we checked into the Freehand Chicago, located in Downtown Chicago. The Freehand definitely has a hipster-ish like feel, the hotel filled with dark lighting and interesting pieces of art. All the workers were extremely nice and suggested some great bars for us to hit for the night. Our room included a queen bed, a TV, night stands, and a beautiful bathroom. Definitely had a comfortable stay. 

For our first night, we hit up a bar walking distance from our hotel. Our hotel was walking distance to almost everything we did, and we had a wide array of food and drink places to choose from. We decided on a sports bar called Theory, which had great music and good vibes throughout the whole night. We went to bed around 3am that day. 

The next morning on Sunday we woke up around 8:30 and headed to the Museum of Contemporary Art. The exhibit we came to see was the "I Was Raised on the Internet" which included videos,  virtual reality and many hands on activities. 

After that exhibit, we took a LYFT to Wrigleyville to grab a quick bite and drink before we headed into the Chicago Cubs game at Wrigley field. Wrigley Field is hands down my favorite baseball field. It was such an intimate style field. You felt as if you were sitting with the players. The fans were fun and the vibes were so positive throughout the scorching hot day. Once the game was over, and the Chicago Cubs won in the extra inning, we got back to the hotel, ordered in Mexican food, and relaxed the rest of the night. 

The next morning, on Monday, we woke up early after having an early night's sleep. We got our stuff packed to check out, and headed to one of the Chicago beaches. The beach, which was actually Lake Michigan, was so beautiful and surprisingly clean. Mike and I were able to see our feet through the water, and even though the water was extremely cold, it was cool to say we swam in Lake Michigan.

After an hour at the beach, we decided to walk back to the hotel, shower, and go to Giordano's for some Chicago Deep Dish Pizza. God, was it filling but delicious! We decided to take our leftovers and give it to a homeless person as we walked to our next event, the 360 Chicago.

The 360 Chicago is at the Hancock Building, on the top floor. It is floor to ceiling window, on every single wall, that allows you the opportunity to view the whole city of Chicago. It was a clear sunny day and the views were absolutely breath taking. Mike and I also did the TILT which is located at the 360 Chicago. The TILT is an experience where you stand on glass and it leans you downward into the Chicago City Streets. It was an unreal experience and I definitely recommend it. 

After 360 Chicago, we walked over to the Wendella Boat Tour. Our tour was located on the Chicago River, and focused on the architecture of Chicago. Our tour guide was an architect, so it was great having him teach us the history of Chicago, why things were originally made, and what they are used for now. It was cool to see the building Ferris Buehler's dad worked at in the movie "Ferris Buehler's Day Off," as well as the building Al Capone had his SpeakEasy. The river was so clean, and then cool from the water was definitely a refreshing break from all the walking we had done so far that day. But, the walking was not over just yet.

We walked over to Millenium Park to see the famous "Bean." We took some pictures, and decided to head back to the hotel. Of course, we couldn't go back to the hotel until we ate some more Chicago famous food. We stopped at Garretts Popcorn, where we ordered a small bag of mixed popcorn.... IT WAS DELICIOUS. Next door, we stopped at Stan's Donuts, which very much reminded me of Krispy Kreme.

We finally made it back to our hotel, and eventually made it to the airport and back to NJ. We got a 10pm flight back to NJ, and due to the time change, we got back to NJ at 1am.

Mike and I really did fall in love with the city. The people were friendly, the streets were clean ( MUCH CLEANER THAN NYC) , and there was so much to do! Compared to NYC, it was definitely cheaper as well, which was a nice surprise. We can not wait to come back in the near future (definitely before the winter) and check off more things off our TO DO list. 


- Go to a Chicago Beach

- GO TO THE SEARS TOWER ( Tickets were sold out when we went to book!)

- If Sears Tower tickets are sold out GO TO 360 CHICAGO

- Go to a Chicago Cubs game

- TRY CHICAGO DEEP DISH PIZZA- Specifically from Pequod's Pizza

- Go on a Wendella Boat Architecture Tour

- Try Garretts Popcorn

- Go to a Rooftop Speak Easy (IF you are of age)

- Go to a museum, doesn't matter which one!

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