You can't just ignore an email saying you can fly to Chicago, IL for under $300 bucks. You check your calendar find some randon days you can sneak away and you book that Airbnb.
I had never been to Chicago before and always love exploring new cities when I get the chance. And let me tell you, I LOVED IT every second of it. All the neighborhoods I got to explore were amazing, and the downtown area was so great. My Airbnb was located in West DePaul and I would 100% stay in the area again. It was close to all the trains and all the best food. And OMG the public transit system, WOW it was fantastic. You know you're an adult when you get excited about being able to take the train to all places. I didn't miss driving at all and wish all cities had great public transit. Chicago does the outdoors right, there are so many huge areas where you can just be in nature and decompress. Between the parks (large and small) beach area and free quite museums it was easy to find little getaways from the hustle of the city. I will say that I ate the deep dish pizza and once was more than enough and I also ate their normal pizza and would also say once was more than once.
Below are some of the shots of some of my fav. spots to eat. Breakfast places were the winners every day. I think it's become my favorite meal to eat. You can make almost anything count as breakfast if you just throw an egg on it.