You’ve touched down at O’Hare or Midway and picked up your rental car. The natural question is: where to next? If you’ve come to Chicago for business, we hope you set aside a few days to explore and have fun! If you’re in the Windy City for vacation, you probably already have some ideas about where to go and what to see. Having a rental car will help you get around town and see more sights in less time.
What follows are a few of the most promising Chicago areas to visit, along with their must-see attractions. There are enough sights in Chicago to suit any taste, so feel free to create an itinerary that fits your unique interests. Also, remember that we just want to help you get started – there are more things to do in the Windy City than can be covered in any list!
Lake Shore Drive
The first stop on your Chicago driving tour isn’t a stop, technically speaking. Chicago weather is famously harsh in the winter, so this ride is best suited for a warm summer evening – with the windows rolled down, your favorite songs blaring, and the breeze of Lake Michigan keeping you cool. The scenic Lake Shore Drive will take you as far as you want to go while soaking in the sights of Lake Michigan; and if you have the time, you can head all the way into Indiana.
In and around The Loop
Once you’ve taken an introductory drive, it’s time to park and pay a visit to the city’s top destinations. If you’re a first-time visitor to Chicago, you can begin getting acquainted with the downtown area, particularly The Loop – which is ringed by L train lines and adjacent to Millennium Park. Be sure to take a photo by the iconic sculpture known as Cloud Gate (AKA “The Bean”) to kick off your Chicago expedition.