The lobby of the Drake Hotel

Chicago might not come to mind when you think of popular romantic comedies but the folks at Time Out Chicago Magazine have come up with a walking tour to turn that notion around. The Windy City has hosted scads of silly chick flicks, from My Best Friend’s Wedding  to The Break Up and thanks to Time Out, you can trace key movie scenes with an hour and a half walking tour that will lead you through about three miles of the downtown and Gold Coast areas.

Start at Twin Anchors at 1655 N. Sedgwick, where 2000′s Return To Me, with Bonnie Hunt, David Duchovny and Minnie Driver  hung out in the rib joint made over into an Italian restaurant in the movie. Head around the corner to Lincoln Park, where following the North Ave. underpass will take you through the jogging scene that Jennifer Aniston trod during 2006′s The Break Up.  Walk  south to the Drake Hotel at 140 E. Walton, where Julia Roberts devised evil wedding sabotage in 1997′s My Best Friend’s Wedding.  Continue east to Bootleggers, at 13 W. Division. This rowdy bar played host to the antics of 1986′s About Last Night, although Demi Moore and Rob Lowe mysteriously refer to it  as Mother’s, a famous bar located across the street.  Stroll east to 126 E. Chestnut, where the gorgeous Gothic revival Fourth Presbyterian Church was used for the nuptials during My Best Friend’s Wedding.  End the tour by going south to 175 N. State, where the Chicago Theater provided the stage for the final scene when Julia Stiles performs her Julliard audition in my personal favorite, 2001′s Save The Last Dance.  Cap off your Chicago rom com tour by heading back to the Drake Hotel and experiencing their elegant high tea service, complete with a live harpist.

Photo courtesy of The Drake Hotel