A direct ripoff of @carolineoncrack 's LA list. These are all summer-themed...I'll be back with a winter-appropriate list when I'm emotionally ready to acknowledge that season again.
  1. Parson's
    I have two words for you: Negroni slushy. Enormous patio/beer garden and fried chicken to die for.
  2. Fountainhead's rooftop.
    Skip the douchey hotel rooftops downtown and instead marvel at this fancy corner bar's rooftop garden and its extensive beer and whiskey lists. If you start to feel a little too tipsy, order the smoked hummus as a snack.
  3. NoMi Lounge.
    OK, I overstated that last point. Here is one non-douchey hotel bar downtown where you can and should sip a classy cocktail.
  4. Handlebar Cafe
    It's everybody's favorite bike messenger-themed, (mostly) vegetarian cafe! Big outdoor space, solid beer list. I spent many, MANY nights there when I still lived in Wicker Park.
  5. Moody's Pub.
    Expect picnic tables, pitchers of questionable sangria and large groups of amiable north siders. Order the sloppy joe.
  6. BONUS RAINOUT OPTION: The Paper Machete at the Green Mill
    Granted this only applies on Saturday afternoons (3-5pm weekly), but the Machete defines itself by how it lets you daydrink in one of Chicago's coolest bars. (Al Capone hung out there, so you know that shit is cool.) The show is free and features Chicago's smartest comedians, writers and culture vultures talking about current events. Plus occasional high profile comedians from out of town.