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As skaters glide across Glenwood Roller Rink’s polished hardwood, the lights flashing over their heads might as well belong to a time machine. That’s how convincingly the rink captures the essence of those carefree days when you first held hands in couples skate or landed your first flawless triple axel. A team of DJs keeps things festive throughout roller-skating sessions for all ages, pumping out upbeat tunes to fuel the nightly festivities. They wisely opt for a soundtrack tinged with soul on themed nights for adults.

656 W Holbrook Rd
Glenwood,
IL
US

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.

465 N McClurg Ct
Chicago,
IL
US

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.

1130 W Chicago Ave
Chicago,
IL
US

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.

1558 E 53rd St
Chicago,
IL
US

Even at the peak of Chicago’s hottest summers and meanest winters, the Johnny Sprockets team can be seen riding on the lakefront path or dodging cabs in the bike lanes. Owner Manuel Tenorio makes it clear that the staff members are cyclists and not just salespeople. They learn about their inventory first-hand, and they outfit their customers with equipment that they themselves endorse.

The team also services and repairs all types of cycles. With each visit, they perform a free, no-obligation estimate to assess cycle health and suss out any potential troubles. They can perform minor repairs on the spot, and they also accept appointments for tune-ups, overhauls, or a bike’s first haircut.

3001 N Broadway St
Chicago,
IL
US

Originating as a bicycle-repair shop on Chicago's South Side in 1944, Kozy's Cyclery now consists of four store locations across Chicago, helping make it the city's premier bike store for the past 60-plus years. Along with a complete stock of bicycle clothing, accessories, parts—and, of course, bikes—the three-generation, family-owned store cares for its bicycle-riding customers by offering professional bike fittings, test rides, and two free tune-ups with every new bicycle purchase. Kozy's sells more than 250 bikes for each rider's unique needs, from mountain bikes and cruisers to fixed gears and multispeed commuter bikes.

219 W Erie St
Chicago,
IL
US