If you are traveling to Chicago and plan on being there for more than a day, I highly recommend making arrangements to get a rental car. I first visited Chicago on a business trip around six years ago. I was there for five days, and I did not get a rental car. On the plane ride home, I spent most of my time thinking about all of the great things that I missed out on because I had not gotten a rental car.

Thanks to the availability of taxis in Chicago, it’s not like I wasn’t able to get around. However, as I sat on the plane thinking about my trip, I just realized that there were a lot of other fun things I would have done in Chicago if I would have had a rental car.

Fortunately for me, since my initial trip to Chicago, I have had several other opportunities to visit the Windy City again. And each time that I have gone (with the exception of the time I was only there for nine hours, which is a story in itself), I have made sure to make prior car rental arrangement to get the full Chicago experience.