We've probably done this tour a combined 25 times, but would again in a heartbeat. It's a great way to see the city, learn some Chicago history, and see some incredible examples of many styles of architecture. Guides are very knowledgable. This is the company we recommend. You can pick up from one of two locations. Grab a drink onboard too.
If you've been on the High Line in NYC, this is Chicago's version. The 606 is a former train track converted into park and path. Enjoy a run or a leisurely walk and check out a few neighborhoods. The 606 runs for 2.7 miles (one way) and has 12 access points so you can decide the right distance for you.
If you're in early and watch to catch a game the Cubs are in town playing the Brewers at 1:20pm at historic Wrigley Field. We live ~ 3/4 mile south of Wrigley and a cubs day game is definitely an experience to check off your list. Take in the atmosphere, and spend some time in Wrigleyville - the surrounding neighborhood...err... bars.
Our absolute favorite theatre in Chicago (and not just because Lindsay's on the board, or David Schwimmer was a founder). Lookingglass does an amazing job producing many original works and are top-notch storytellers. Catch a Friday matinee or Friday evening show. We can't wait for this one!