The Southerly

Distance: 24 miles
Route: TCX / GPX
Ride time: 1-2 hours

Perhaps the best way to view Chicago's true splendor is taking a ride on Chicago's lakefront path. The path stretches 18 miles from north to south, and while heading north is a great way to escape the city, heading south is a great way to experience it.

The ride starts at Monroe avenue and Lake Shore Drive, where the path cuts a straight line south to Museum Park, and then juts out into the lake, snuggling you tight as you spin yourself around the outer edge of the Shedd Aquarium. Coming up for air, you'll breeze past the hulking Solider's Field and McCormick place before escaping into the south side of Chicago's lakefront - full of public beaches and stretches of gorgeous prarie-restoration. A few more miles gets you down to Promontory Point where you'll turn around, or … 

If you've never seen a WW II Nazi Submarine which was captured by the allied forces and dredged back across the Atlantic ocean, through the north St. Lawrence river, and down thru the great lakes corridor, well, this is your chance. The Science  & Industry Museum is right across the street from the flip of this ride at Promontory Point. Take a bike lock and some street shoes, and be awed by merely stepping inside this vast, last-standing building from the 1894 Colombian fair.