Try this Boulevard for starters!
Head west starting at any spot on Diversey Avenue. If you start at the lakefront on Diversey Ave, take it west to Logan Boulevard in Logan Square. Approximately 6 miles. Head South on Logan Boulevard all the way to beautiful Humboldt Park. Approximately 2 miles. Ride throughout the many bike trails in this massive park, check out the lagoon house, the gardens and the food vendors. Circle around and ride north on Logan Boulevard. There are plenty of great shops and eats right in the square.