START Twin Anchors END Chicago Theatre DISTANCE 3.3 miles TIME 1 hour, 30 minutes
Start your walk d’amour in Old Town at Twin Anchors (1655 N Sedgwick St, 312-266-1616), where director Bonnie Hunt based 2000’s Return to Me. For the film, which featured Hunt alongside David Duchovny and Minnie Driver, the rib joint was re-dressed as O’Reilly’s Italian Restaurant, and for five weeks, it sported a false facade Monday through Thursday (it was dismantled each weekend to accommodate Twin Anchors’ regular clientele).
Round the corner and head east on Eugenie Street, which turns into LaSalle Drive. Here, you’ll ditch city sidewalks and enter Lincoln Park. Take the walking path that hugs LaSalle to the south, and make for the lake. Follow the North Avenue underpass to the lakefront trail, then head south. As you stroll by the chess pavilion, take in the spectacular skyline ahead. At this spot, Jennifer Aniston is seen jogging in 2006’s The Break-Up. (During filming, this area was a magnet for paparazzi clamoring for photos of Jen, fresh off her split from Brad Pitt.)
Continue south along the trail and notice the iconic pink blaze of the Drake Hotel’s (140 E Walton St, 312-787-2200) neon sign. In 1997’s My Best Friend’s Wedding, the prenuptial festivities and Julia Roberts’s relationship-sabotaging antics take place at the hotel’s Gold Coast room, as well as guest rooms.
Exit the path at Division Street. As you head east, time-travel to 1986, when the exterior of party bar Bootleggers (13 W Division St, 312-266-0944) was immortalized as the hangout in About Last Night. Confusingly, in the movie Demi Moore and Rob Lowe refer to the bar as Mother’s, which is the name of the bar across the street.
Walk east to State and proceed south. Hang a soft left on Rush Street, then go east on Chestnut Street, where you’ll arrive at Fourth Presbyterian Church (126 E Chestnut St, 312-787-4570), whose sanctuary was used for the nuptials in My Best Friend’s Wedding. Round the corner of the stunning Gothic revival building onto Michigan Avenue and enter the sun-dappled courtyard for some peace and quiet before heading back into the Mag Mile fray.
Make another My Best Friend’s Wedding stop by strolling south along Michigan Avenue. At the Chicago River, cross the bridge, then descend the stairs at Wacker Drive. Meander west along the river; it’s under the Wells Street Bridge where Julia Roberts and Dermot Mulroney share a tender slow dance while on an architecture river cruise.
Ascend the stairs at State Street and head south one block to your final destination: the Chicago Theatre (175 N State St, 312-462-6300), which has the dubious distinction of housing the stage where Julia Stiles performs a wooden dance routine for her climactic Juilliard audition in 2001’s romance Save the Last Dance.
View Rom-Com in the Gold Cost Walk in a larger map