Dating in Wicker Park
In shortWicker Park is known for its shops, bars and music. It is easy to reach on the Blue Line. Good for a date that can drift from a walk to dinner.
A first date idea
The 606 trail
The 606 is a raised trail that runs 2.7 miles along the old Bloomingdale line, between Ashland and Ridgeway avenues. It has 12 access points, about every quarter mile, and is open from 6am to 11pm. Wicker Park's shops and restaurants are close to the Damen stop.
Source: Chicago Park District: Visit the 606, checked 8 November 2026
Walk a stretch of The 606, then eat near the Damen stop.
For more ideas, read free dates in Chicago or summer dates on the lakefront.
