Things to Do on a Date in Chicago

Finding something to do on a date in Chicago is like trying to find sand on the beaches of beautiful Lake Michigan in downtown; they are everywhere, and you don't have to look hard to find them. They city is filled with activities that are perfect for couples looking to spend some quality time together. The romance of the city makes even walking a great thing to do on a date.

  1. Catch a Day Game at Wrigley

    • From April to October, Wrigley Field is home to Chicago's favorite baseball team, the Cubs. Nothing is more iconic, or fun, in Chicago than sitting above the ivy in the bleachers with the rest of "The Bums," sipping a beer in the sun and watching the great American pastime slowly unfold. Before and after the game, walk around the Wrigleyville and nearby Lincoln Park neighborhoods, two of Chicago's nicest. Each is filled with a plethora of shops, cafes and restaurants, and the lake forms the eastern border for both.

      Wrigley Field
      1060 W. Addison St.
      Chicago, IL 60613
      (773) 404-CUBS
      chicago.cubs.mlb.com

    Watch the Sunset from the Willis Tower

    • Visitors of the Willis Tower (formerly the Sears Tower) travel to the Skydeck on the 103rd floor in just 60 seconds. From there, visitors can see out over the surrounding area, over the lake and even Wisconsin, Indiana and Michigan. Visitors can then walk out onto glass balconies (Skydeck Ledge) and stand above the city. If timed right, visitors have an unmatched, unobstructed view of the setting sun and its changing colors as it brings on the night.

      The Skydeck
      233 S. Wacker Drive
      Suite 3530
      Chicago, IL 60606
      (312) 875-9696
      theskydeck.com

    See Live Theater

    • New York is not the only place with great theater; in fact, Chicago is home to more than 200 theater companies, most notably the Steppenwolf Theater and Second City. Chicago's main theater district, where Broadway-caliber plays and musicals can be found, is located on the north side of the Loop, but theaters are strewn throughout the city. Playbills constantly change, so check dates and times before traveling. For popular events, it is best to book well in advance.

      Chicago Events Information
      explorechicago.org

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