1 Rosehill Cemetery
An endless choose-your-own-adventure jaunt through a North Side graveyard may seem macabre, but it’s insulated from city noise and has zero stop signs. Bonus: Target is across the street for diaper and formula runs.
2 Peterson Avenue from Pulaski Road to Milwaukee Avenue
This route ends at Superdawg, where you can idle in your car with a hot dog, a malt, and your smartphone as long as you want.
3 Sheridan Road from Rogers Park to Winnetka
The curves are sure to make your baby pass out while you enjoy the passing real estate porn.
4 Lake Shore Drive from Soldier Field to Jackson Park
Not a stoplight is to be found between the stadium and Hyde Park. Loop around the park to head back north. (But during Bears games, make like Tarik Cohen and hightail it far, far away from this route.)
5 Lower Wacker Drive
The dimness gives your baby an extra nudge during daytime naps. Vibrations from the overhead grates provide a dose of white noise. Emerge by the Old Main Post Office and cut over to Lake Shore Drive to start the whole path again.