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.
In a shop lined with more than 100 bikes models from all around the world, Upgrade Cycle Works' pro mechanics channel their love of cycling whether they are aligning the frame on an old single speed or fitting guests for a brand new road bike. During the fit process, staffers employ the same computerized system used at the Olympic training center as opposed to tracing your body outline on a large piece of construction paper. Next, they’ll help guests choose from bike brands such as Felt, Masi, and Raleigh, and an in-store selection of rides that includes road bikes, single speeds, and hybrids.
In Upgrade's workshop, pro mechanics perform comprehensive tune-ups and repairs, revitalize faded paint jobs, replace punctured wheels, and align frames. The staff also hosts repair clinics to teach cyclists how to fix flat tires and adjust brakes.
With a fleet of futuristic segways and classic beach-cruiser bicycles, Bike and Roll Chicago outfits travelers with wheeled transportation to explore the city's paved surfaces. Tour guides lead groups through Millennium Park and along the lakefront to catch the skyline when illuminated by sunrises or backlit by one of Chicago's many moons. Misty Lake Michigan breezes ruffle riders' hair peeking through helmets as they pass by sailboats swaying lazily in the harbors and fishermen casting lines for trout and perch. Bike and Roll Chicago designs routes around classic architectural landmarks such as the Shedd Aquarium and Field Museum as well as popular neighborhoods home to a number of restaurants and art festivals.
Chicago Rickshaw releases its fleet of pedal-powered, open-air cabs through the thoroughfares of the city, meandering up to three weary travelers on a one-hour jaunt of urban sightseeing. Rickshaws provide a distinct vantage point and remain an environmentally chummy mode of transportation second only to attaching one end of marionette strings to your legs and the other end to methodically flying pigeons. Up to three gallivanters, plus the driver, can fit in the motorless coach as it lopes small groups around the City of Big Shoulders and through many of its public easements, including areas not accessible to large motor-propelled carriages.
Star Struck is the official provider of authentic Blackhawks and Bulls apparel, and carries tons of tees, caps, and more for all Chicago sports teams. Stay warm with a Blackhawks tassel knit hat ($15), or put your Groupon toward a Bulls playbook pullover hoodie by Adidas ($45). Pass yourself off as number one with a Jay Cutler women's jersey ($65), go vintage with a faded Blackhawks zip hoodie ($65), or layer for the Chicago cold with either a Blackhawks or Bulls three-in-one T-shirt combo pack ($30). Sports apparel also makes a great gift for all your expecting friends, whose soon-to-be babies would be naked if not for the Cubs onesies ($16) you so graciously provided.
"Pump Pedals, Not Gas" goes the motto for On the Route Bicycles, a thoroughly modern bike shop committed to swift travel by eco-friendly means. Like any good bike shop, the unmistakable scent of tires drifts down thoroughfares lined with all manner of biking accessories, from lights and helmets to locks and biking bags. All of this in addition to the latest bike models from the likes of Trek, Cannondale, Bianchi, Electra, Handsome, and Raleigh, who provide a selection of city bikes, road bikes, and performance models. As a bonus to their community, On the Route even includes an air pump outside the store, where passing bikers can juice up their tires or blow those pecking birds from their head.