Chicagooooo!

Welcome back! Thank you for joining me again to hear about my Chicago experience! Let me begin by giving you a little back story on how we ended up in Chicago. My sister Olivia, friend Alina and I began taking trips about 5 years ago.

Our first trip together was to New York City and our second one was to Atlanta. These first two trips we agreed on unanimously. After this we decided it would be cool to each choose two destinations, put them in a hat and draw our next vacation destination. Pretty cool concept right? So while we were in Atlanta we each put two destinations in a hat and we had a guest draw one. Los Angeles was chosen so that would be our next destination. The next year we chose Seattle and then this year it was Chicago. While in Chicago we drew our 2020 destination and as you can see from the picture above, we will be visiting Charleston, South Carolina! If you have any tips or suggestions I would LOVE to hear them!

Ok, now that you know a little about how our yearly friend trip works let’s get into our Chicago trip!

Flights:

We try to book our flights as early as we possibly can once we find a weekend that works for all 3 of us. That is probably the trickiest part. This year we booked in April I believe for our late June trip. I took advantage of my American Airlines miles to book one of my flights. I only had enough miles for a one way so I booked my return with American Airlines using points and I booked my flight there through Southwest. This allowed me to save some money! I believe I paid around $100-$120 for the one way to Chicago. I do not have an American Airlines Credit card but if you have not heard of American Airlines Eshopping, you need to check it out. I have an AAdvantage account and with that I can set up an account with the Eshopping page and when I am going to do some online shopping I go directly to the Eshopping page search for the store I want and it will redirect me to that store’s page. This way I earn points on my American Airlines account by doing something I was going to do anyway. Check it out! It is pretty great! We flew in Thursday morning and left Sunday night.

Airbnb:

We stayed in an airbnb in the Pilson neighborhood. It is located a little south of downtown. We loved the neighborhood. It is a predominantly latino neighborhood. You will find vintage shops, independent coffee shops and quaint cafes near panaderias, tortillerias, and restaurants serving authentic Mexican food. There is also a Giordano’s in the neighborhood! We loved the relaxed feeling of the neighborhood and would definitely stay here again when we return to Chicago.

A view of our lovely Airbnb

Transportation:

We took Lyfts the entire time we were in Chicago. They do have public transportation but we decided to go for the shared ride option. We spent about $45 each for our Lyfts rides the entire weekend and there were 4 of us. One person booked all the Lyfts and on the last day we just split the cost.

Thursday:

We arrived at the airport at 11. We had a problem because we could not check into our airbnb until 3 but we were going to attend the Cubs vs. Braves game at 1pm. After doing some research we found Luggage Hero. We had never heard of it but apparently businesses will hold your luggage for you. After reading the reviews, we took a chance and left our luggage at a cafe near Wrigley stadium. It was a very easy and convenient process. From there we walked to Wrigley stadium.

The stadium was awesome and watching the game was a great experience. We ate hotdogs and enjoyed the game. The fans there were very passionate about their team and it was evident by their excitement. You could tell these people were die hard fans! Everyone gave each other a high five when a run was scored even if you didn’t know the person. After the game we picked up our luggage and headed to our airbnb. The rest of the day we relaxed a bit and headed to dinner at Giordano’s! This was one of the most mentioned places when we were looking up what to eat. Of course we had to try the chicago style deep dish pizza! I did not think that I would like it much at first, but once I tried it I fell in love! The amount of cheese was out of this world. We wrapped the day up by going to watch Toy Story 4.

Friday:

We got up early today to go to the Skydeck at Willis Tower. You know all the pictures you see of people standing on glass over the city. This is it! The place opens at 9 and every website advised us to get there early because it gets packed! We left the airbnb at 8 am and got to the Willis Tower at 830 am. Apparently we were a bit too early because no one was there and the doors were not open yet. Around 850 they opened the doors and we were first in line. I am glad we got there early because about 5 minutes after they let us in, all the people started entering and it looked like it would never end. When they let you enter there is quite a bit of history about the city and the tower as well as a souvenir shop. We ignored everything and headed straight for the glass area to get our pictures. We finally found it and I was shocked to see that it was only a ledge made of glass. I expected like a whole room I guess. But, there were 2 ledges and ropes so people could line up to take pictures. We were first and were shocked to learn that if your group had 2 people you have 30 SECONDS to take pictures. If you have 3 or more you get 90 seconds. This seemed like no time at all. So we began taking our pictures and the people literally have stopwatch to tell you when your time is over. We felt unsatisfied with the pictures and then the stop watch man told us we could get back in line to take more pictures. We got back in line about 3 times, please enjoy some of our pictures below!

After the skydeck we passed the time at Mojo’s coffee shop while the Hampton Social opened. The Hampton Social is a bar/food business. It is a very beautiful place and has many instagramable areas!

After this we headed to the Merchant Market for lunch where we found many different restaurants which was perfect so we could all eat what we wanted. We visited the Riverwalk next and enjoyed the views of the boats passing by. It was nice because there were several chairs down there where you could hang out.

Our next spot was one of my favorites! We headed to the Adler Planetarium where we were able to get these amazing views of the city! There was no need to enter the museum we simply relaxed on the grass and took a million pictures!

Our next stop was the XO Marshmallow shop. They had the cutest decorations and sold many different flavors of marshmallows! I tried the cookies and cream marshmallow and the fruity pebbles marshmallow. They also sold smoothies and other drinks!

Our last even of the day was attending the White Sox vs. Twins game! We had amazing seats at 1st base on the 3rd row. The atmosphere here felt different than the Cubs game. This game had more of a hometown vibe. I really enjoyed it and I am glad we got to experience both games! I am not a huge baseball fan and even I am glad we had these games on our itineraries.

Saturday:

We started with Brunch at Cindy’s. It was a very fancy place, I almost felt out of place there. It is a rooftop bar/brunch place and it was said to have a great view of the city. It sure did! The food was amazing, we shared an order of chilaquiles and a half order of pancakes. That was enough for the 4 of us. Their drinks were delicious and super strong!

After brunch we headed to see the Bean and millenium park. It was a hot day! We quickly took our pictures and then tried to keep cool in the shade. We saw some beautiful gardens and interesting architecture in this area. We spent most of the day walking around the area and doing some souvenir shopping.

We had dinner at Canton Regio in Pilson that evening. It was absolutely delicious! It was one of my favorite meals! Our last event was a comedy show at The Second City. We watched a show called She The People and it had us laughing the entire time. I definitely recommend the shows here and specifically this one.

Sunday

Sunday was our last day in Chicago but we had a late flight so we were able to squeeze in a couple more activities. We took the Architecture and Lake Tour. It lasted about 1.5 to 2 hours. It was nice to sit on a boat and hear all of the interesting facts about the buildings. I recommend to include the lake in your boat tour because that is where we were able to get some of the best views of the city!

After the boat tour we had lunch at Kanela Brunch place where we had a very delicious cinnamon roll as well as some yummy food! This place is a must if you are in Chicago.

Our last event was visiting the Navy Pier! There were many shops and dining areas. Sadly when we arrived at the Navy Pier a storm started and it began raining really hard which made us have to stay indoors. But, if you are looking to buy souvenirs I suggest to wait until you visit the Navy Pier! We found many shops with items at great prices!

As you can see it was windy!

Overall Chicago was amazing! Thank you so much for reading my blog, if you have any questions about anything on our trip leave them in the comments and I will answer them for you! Also if you made it to the end of this post let me know below if you prefer to relax on your vacation or keep yourself busy with activities?

Until next time!