- $25 for a Fright Hike bike tour (a $49 value)
During the third-annual three-hour tour, professional actors guide groups through approximately 8 miles of scary stories and sights. Cyclists start out at Bobby’s Bike Hike world headquarters, ride through a former cemetery to learn about Resurrection Mary, and visit a reportedly haunted site of a mass drowning on the Chicago River. The tour begins at 7 p.m. on Wednesday, Friday, and Saturday evenings from October 1–17; nightly tours are available from October 18–31. View the schedule. The deal includes bikes and helmets, but it doesn't include guide gratuity or a bouquet of Resurrection Mary's favorite flowers.
Bobby's Bike Hike
Inspired by a love of fitness and a passion for travel and tourism kindled within him by his late father, Jeremy Lewno founded Bobby's Bike Hike to create an interactive Chicago biking experience. He named the company after his dad, Bob, an Arkansas bus-tour operator who taught him to focus on service quality over quantity. That advice has clearly paid off, as the business's guided tours have earned a number one ranking for activities to do in Chicago on TripAdvisor and the title of Best Organized Bike Ride from the Chicago Reader in 2010.
During the tours, which include rented bicycles, guides lead groups of about 20 riders past Chicago icons in Millennium Park and on the Museum Campus, or direct them to samples of pizza, hot dogs, cupcakes, and beer in and around Wrigleyville. The crew has designed a Tike Hike tour for kids 10 and younger, a historic Hyde Park tour that pedals past the home of President Barack Obama, and a mansion-studded lakefront tour, during which riders may glimpse Oprah waving or handing out complimentary helicopters at her main residence. Patrons can also rent Schwinn, GT, and Cannondale Comfort bikes, mountain, road, cruisers, and tandem bikes to explore the city on their own.