There's more to experience in Chicago than any one weekend can allow, many people go for its architecture but I went for its food. And it'd take me many more weekends to get a true sense of what the city has to offer, alas, I only had two days so I scoured online and asked for recommendations, but I think the best way to experience the city is to crash with a friend and hijack their weekend. I was fortunate enough to stay with a friend (thanks Josh) who enjoys food as much as I do, and despite only having lived in Chicago for a year he was well versed in where to go and what to eat. So that's what we did.