Destinations

Planning a trip to Chicago on a budget? Chicago can be expensive but fortunately many of the best things to do and see in Chicago are totally free! Here are my top picks for the best free things to do in Chicago.… Continue Reading →

The most romantic things to do in Chicago for couples in 2025. Whether planning a weekend getaway in the city with your significant other or looking for unique Chicago date night ideas, these are the best activities to enjoy in… Continue Reading →

Not sure what is the best time to visit Chicago? I have lived in Chicago for most of my life so I’ve put together an updated month by month guide to help you figure out the best time to go… Continue Reading →

Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas in 2025 – from free and cheap date ideas to special date ideas for those looking to impress. Whether looking… Continue Reading →

Searching for what there is to do in Chicago this summer? Below are the best things to do in Chicago in the summer of 2025 (from a local) – including the best summer 2025 events and festivals. I suggest bookmarking… Continue Reading →

Searching for what to do in Chicago this October? Here are the best things to do in Chicago in October 2025 (from a local) – from the best October events and festivals to fun fall and Halloween themed activities. Chicago… Continue Reading →

Looking for what to do in Chicago this September? Here are the best things to do in Chicago in September 2025 including all of the best September 2025 festivals and events. I suggest bookmarking this blog post as I will… Continue Reading →