There are a few entrances onto the lakefront trail. The link shared below provides a map for each one. If you like to bike, you can rent a Divvy bike for rather cheap! Just download the Divvy app and you will find Divvy bike racks nearby.
The Riverwalk offers plenty of food and beverage spots, while enjoying the activity on the river. You can also access several architecture tours from the river or rent your own personal boat.
Who doesn't love a good old comedy club? Another comedy club to check for shows is Laugh Factory: https://www.laughfactory.com/chicago.
Cheezborger. Cheezborger. Cheezborger. A burger staple in Chicago! If you watch Saturday Night Live- you probably know of this place (video here: https://tinyurl.com/cheezborger). There is a newer location on Navy Pier if that is more convenient for you.
We love a good rooftop bar. One of our favorites is LondonHouse, but the link on the below 'View' button lists out several others.