Chicago: The Rides

What's excellent about cycling in Chicago is what its cyclists choose to make of the city and its surroundings. Chicago doesn't have mountains. Or hills. There is the occasional mound. Otherwise, it's flat. You can ride 40 miles north and back and log only 300 meters or so of ascent. For the avid cyclist, that means tightly packed, hard-paced group rides. For the leisure-ride inclined, it means easily-accessed destinations for coffee, beer, and visual splendors like Bahai temple (an easy 24 mile out/back ride from the heart of Chicago). The lakefront path alone stretches a full 18 miles and has stunning views of the skyline, historic industry, the park and lake, and access to many of Chicago's best features. 

Following are four quintessential Chicago rides*, each with options to stretch it out, or stop along the way. 

* Unless otherwise noted, expect some riding on roads with cars.

 
 
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Cider House Rules
Cider House Rules

Distance: 77 miles | Level: Challenging

Just over an hour outside of Chicago is, arguably, the best riding within a day's travel of the city. There's plenty of rolling, lush riding on quiet, well-groomed roads as well as some excellent eating and drinking options to refuel at before heading back to the city.  

The Wolfpack
The Wolfpack

Distance: 39 miles | Level: Intermediate | Time: 2-3 hours

Extending out past Chicago's Lake Front path, this urban ride swoops into Indiana for a loop through the Wolf Lake area before returning you back to Illinois for the city's best skyline and lake views. 
The Northerly

Distance: 60 miles | Level: Intermediate | Time: 2.5-3.5 hours

This mostly out and back ride follows the undulating Sheridan road past the famous Baha'i Temple all the way up to a beautiful old military base called Fort Sheridan. It's the most popular route for the city's avid cyclists, bar none.   

The Southerly
The Southerly

Distance: 13.8 miles | Level: Easy | Time: 1-2 hours

The Southerly meanders down Chicago's south side shoreline path, taking you through Museum Park, Soldier Field, all the way down to Jackson Park - the location of the 1892 Columbian exposition. Extra miles will carry you Chicago's industrial past, across the Indiana border to do a sweeping loop around Wolf Lake.