Dating in Logan Square
In shortLogan Square has wide boulevards, a busy food scene and a neighborhood feel. Plenty of locals walk or bike everywhere. It is a natural place for a casual first date.
A first date idea
Logan Square and The 606
Logan Square has a central plaza with the Illinois Centennial Monument, an easy landmark to meet at. From there, head for The 606, which runs east toward Wicker Park. All its access ramps are accessible to people with disabilities.
Source: Chicago Park District: Visit the 606, checked 8 November 2026
Meet by the Illinois Centennial Monument and walk to The 606.
For more ideas, read summer dates on the lakefront or getting through a Chicago winter as a couple.
