Rent a bike and ride along the city's breathtaking Lakefront Trail with a guide from Bike Chicago, or pick up a free map and take your own self-guided tour. The section of the bike path that winds along North Avenue Beach is featured in the comedy The Break-Up. Keep biking north and you'll encounter the Lincoln Park Zoo, seen in the romantic comedy Return to Me. Check out the new Children's Zoo and Regenstein Center for African Apes. Have dinner at Twin Anchors Restaurant & Tavern in Old Town, one of the oldest restaurants in the city and a favorite of Frank Sinatra's (his tunes are featured on the jukebox). The eatery, known for its zesty barbecued ribs, starred as O'Reilly's Italian Restaurant in Return to Me. Catch a comedy star on the rise at The Second City, the improv training ground for famed comedic actors that include Bill Murray, Mike Myers and the Belushi brothers. Or see a concert at the historic Riviera Theatre in the Uptown neighborhood. This former movie palace was also used as a film location for The Break-Up.

Sail on a Mercury Skyline Cruiseline boat cruise and get swept up in the romance of the river just like the characters who performed an upper-deck slow dance in My Best Friend's Wedding. You'll glide past buildings of architectural note that have appeared in several films, including the Wrigley Building (Road to Perdition, The Fugitive and Mercury Rising), Tribune Tower (The Whole Nine Yards) and Marina Towers (from which a car plunged into the Chicago River in The Hunter). Find waterfront fun at Navy Pier, home to the Chicago Shakespeare Theater, the outdoor Pepsi Skyline Stage, an IMAX Theater and several sightseeing and dining cruise ships. Navy Pier's sky-high Ferris wheel was featured in the comedy Never Been Kissed. Don't miss Navy Pier's spectacular fireworks on Wednesday and Saturday nights from the end of May through the first weekend of September. Have dinner on Randolph Street's Restaurant Row at Marché, a hip French brasserie that was featured in the dance drama The Company. Then catch a Broadway in Chicago show in the historic Loop Theater District. The smash musical Wicked is an open run at the Oriental Theatre.

Spend the morning at the esteemed Art Institute of Chicago, where a trio of wise-cracking high school buddies played hooky in Ferris Bueller's Day Off. This world-class art museum is known for its impressive collection of French Impressionist paintings. Squeeze in some shopping on North Michigan Avenue, better known as The Magnificent Mile®. You'll find a tempting array of shops, including Bloomingdale's, Nordstrom, H&M and the flagship Ralph Lauren store. The photogenic Mag Mile was featured in the romantic comedy While You Were Sleeping. Pop in for a drink at the bar of the Cape Cod Room at the historic Drake Hotel, where the food critic character stayed in My Best Friend's Wedding. Be sure to look for the initials carved into the wood-topped counter by lovebirds Marilyn Monroe and Joe DiMaggio long ago.