With more than 170mi of on-street, protected, shared bike lanes, the Windy City has made cycling the new norm. Sure, it’s bone-chillingly cold for 70% of the year, but Chicago's not messing around: the city's planning to build a 645mi cycling network by 2020. The 18.5mi breezy trail that wraps along Lakeshore Drive, featuring the city’s skyline and the sandy beaches of Lake Michigan, is the most iconic ride for visitors looking to enjoy Chicago’s best assets. The city prides itself on its neighborhoods, so work off that deep dish with a tree-lined ride that cruises by the Osaka Japanese Garden or the Garfield Park Conservatory.
Pro tip: Check out the North Branch Trail, which begins at Devon and Milwaukee Avenues and snakes along the Chicago River up to the Chicago Botanical Gardens. As you venture west toward Wicker Park (which you will, you hipster), be sure to avoid a cyclist’s rush hour nightmare on Milwaukee Avenue; opt for Elston instead.