hotel lobby bars have the best wine selection
some of the best wine & cocktails i've found in chicago has been at hotel lobby bars, like this 2005 merus wine we found at the fairmont chicago millenium park lobby bar
the blackstone hotel opened a new 1960's style cocktail lounge 'timothy hutch' open 5:00-8:30pm daily, featuring live jazz wednesdays and fridays & over 1,600 pieces of commissioned art!
another hotel bar would be in the grey hotel they have a bar called vol.39 with an amazing wine cellar, we had a bottle of paradigm wine from their cellar, that may be my new favorite wine, they also have a lovely menu of cocktails, and an extensive bourbon and whisky list.
one thing i try to do every summer is go sailing ⛵️
i do not have a sail boat, nor do i know how to sail, luckily chicago sailing exists! you can charter one with a qualified captain, they also do rentals if you know how to take to sea, and they give lessons! may be signing up for those next! check out chicago sailing!