I recently took a trip to Chicago!
I've been to Chicago a handful of times and each time I find something new to love. My last visit was in February, the weather was frightening and kept me inside so this time was chilly but manageable.
Most of the time was happily spent with family outside of the city. I pretty much ate constantly and enjoyed catching up with the fam. If your ever out in the midwest go to Steak 'n Shake! It is amazing. Essentially a diner, I think I've only eaten there once but every time I'm out there I go for a shake. They always have your standard flavors plus amazing other creations, and they are open 24 hours.
While I was in the burbs most of my trip, I was able to go into the city several times. My first trip into the city was to go see improv! Chicago is famous for improv and many great comedians and SNL folks have come through the Chi Town circuit. I went to IO for a Saturday night improv show. It was my first professional show and was so much fun. There were amazing comedians and it was just a fun night with my family. IO is downtown right by Wrigley field so we also got to walk around downtown a little and check out a few bars too!
Second City is also in Chicago, if you wanna go to either venue I suggest checking out shows and buying tickets in advance. Shows will sell out and I did see plenty of people tuned away at the door.
Another new discovery for me was the Wicker Park area. It's a little hipster but was fun to walk around for a few hours. There are tons of great little stores and cafes to check out. I got an amazing Chai Latte from Filter and definitely would have spent more time there if I had it. It was so warm and comfy in there. The barista was super nice and the couches looked so inviting.
I also found a great gallery, the Jackson Junge Gallery they had lots of different pieces and had tons of prints and Chicago art if you wanted to take a piece home. If street art is more your thing Wicker Park has tons of it.
Enjoy the pictures and Chicago if you get a chance to go!