Our first date was walking along the Chicago Riverwalk, grabbing drinks along the way. Our favorite spot is The Northman Beer & Cider Garden
Our favorite restaurant! We usually try to get lucky with a last minute bar seat, but you otherwise definitely need to book a reservation at least a month in advance!
The Robey Hotel has an awesome rooftop bar with great drinks and amazing views.
Walk/run/Divvy bike the Lakefront trail. There are entrances to the trail at North Avenue, Division Street, Oak Street.
If you're addicted to oysters like we are, this is a great place for oysters and Gold Coast people watching
The restaurant/bar on the main floor of The Viceroy - cute drinks and good patio!