Chicago area

6 spots. Ideas for 2nd and 3rd dates. Each listing links to Google Maps; many also link to an official website when we have one. Spots marked maps only have no website on file.

All date spots

Hotel / Lounge

Walk / scenic

  • Millennium Park

    2nd-3rd date · Downtown Chicago · Loop

    Outdoor landmark walk; pair with nearby lobby in cold weather.

    Website
  • Navy Pier

    2nd-3rd date · Navy Pier area · Streeterville

    Waterfront walk; can be crowded on weekends.

    Website

Kosher Restaurant

Our kosher restaurant list is not complete. To see what is open and near you, check Jewgo.

  • Shallots

    1st-3rd flexible · West Rogers Park · West Rogers Park

    Kosher fine dining; reservation recommended.

    Website