Chicago has really beautiful architecture and an abundance of art museums— the Art Institute is one of my favourite museums, it’s laid out so well, and you could spend an entire day in the museum easily. When I travel to Chicago I stay at the Freehand hostel; it’s very old school and a bunk in a shared room is $30. If you want to travel to eat, Chicago has a really great restaurant culture, and it’s very accessible for pedestrians and people who use public transit.