Chicago
My friend lived right in the heart of town, so we were a quick walk or metro to anything we wanted to do. I was there in the winter time, so the first thing we did was head to Millennium Square to see the famous bean! I actually love the Bean, for pretty much no reason, but its fun to go get your touristy pictures and the park it is nestled into is huge with a ton to do, especially in the winter. They host all kids of events there and in the winter there is an ice rink. We decided to go ice skating there and it was so much fun.
After that, we walked the main strip from Millennium towards the river and grabbed lunch at a traditional Chicagoan deep dish pizza place called Giordanos. It’s one of Chicago’s most popular. For sunset, we had reserved ourselves a time slot at the “Top of the Rock”, basically Chicago’s version of the Empire State, except you can walk onto the glass out from the building a few feet. Spooky! Make sure you get those reservations in advance as well, as it sells out, and even when you have a reserved time the line is long. There is of course a bar at the top as well. In the evening, we went to an Irish pub in Lincoln Park called River Shannon that is known for being extremely dog friendly, so everyone brings there dogs! It’s a fun little spot to cap the night.