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On an elevated pedestrian and bike path a few bikers ride in opposite directions along metal grid fencing, planted trees and tubular lighting. There are L tracks in the background with a few apartment buildings.
The 606.
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10 beginner bike rides in Chicago

Here are some low-stress routes to get you started on two-wheels in the city

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The 606.
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The thought of cars and buses whizzing by while pedaling in a narrow bike lane can make urban biking in Chicago a frightening prospect for newbies.

But there’s a reason why more commuters are abandoning four-wheeled trips for two: bikes offer regular exercise, save you money, and decrease your carbon footprint. Plus, Divvy’s expansion which will double the amount of bikes and introduce electric, pedal-assist bikes makes biking a lot easier these days.

If you’re just now joining the pedal parade or considering it, don’t immediately try to traverse Clark Street or Ashland Avenue. Here are a number of quieter, lower-traffic, and less stressful routes to act to help you get comfortable and act as your training wheels, so to speak.

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1. North Shore Channel Trail

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N Shore Channel Trail
Chicago, IL

This 6.7-mile path starts near Lawrence and Francisco and runs parallel to the North Shore Channel to Evanston. It will be even better once the construction of a 180-foot-long, bridge over the North Shore Channel is officially completed, allowing cyclists to avoid a Lincoln Avenue detour.

2. West Berteau Avenue & North Lincoln Avenue

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W Berteau Ave & N Lincoln Ave
Chicago, IL 60618

The city’s first Greenway project, this mile-long corridor that prioritizes non-motorized traffic, stretches from Clark Avenue to Lincoln along Berteau Avenue. It also serves to connect four other bike-friendly routes—Damen, Lincoln, Clark, and Southport.

A tree-lined street with two parked cars and a painted bike line.
Bertreau Avenue near Clark Street
Google Street View

3. The 606

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(312) 742-4622
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The 2.7-mile elevated Bloomingdale Trail, casually known as The 606, is a refreshingly car-free way to pass through some heavily trafficked Northwest Side neighborhoods—Bucktown, Logan Square, Humboldt Park.

4. Humboldt Park

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Humboldt Park
Chicago, IL

The three big West Side parks, connected by formal boulevards and dotted with tranquil bodies of water, are great beginner spaces to bike around. Humboldt Park’s Luis Munoz Martin Drive is a great place loop to bike along. Just watch for the occasional alligator.

5. North Elston Avenue & North Milwaukee Avenue

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N Elston Ave & N Milwaukee Ave
Chicago, IL 60642

Of all of the diagonal streets that defy Chicago’s famed grid system—Elston Avenue ranks the best for cyclists who want a low-stress route. The southern portion of the road especially (from its starting point on near Chicago Avenue to Webster Avenue) goes through emptier industrial corridors and features a 1.68-mile protected bike lane.

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#chicago #cycling #sunrise #elstonave #city #skyline

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6. Northerly Island

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1521 S Linn White Dr
Chicago, IL 60605
(312) 745-2910
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The paved path on the southern tip of Northerly Island is a relatively short ride (less than a mile) but it’s a tranquil one filled with wildflowers and prairie grass, and beautiful views of the lake and city skyline. Be warned, it’s partially closed currently as the city repairs some of the concrete damaged by erosion.

A wide concrete path with tall grass on either side. A biker in the distance is stopped gazing at the clouds at dusk.
Northerly Island path
Ryan Smith

7. Douglas Park

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1401 S Sacramento Dr
Chicago, IL 60623
(773) 762-2842
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Avoid it during Riot Fest, but otherwise Douglas Park is a pleasant park to explore on your bike. 

That’s especially true when you travel north on Sacramento Avenue using a curb-protected bike lane that stretches for a quarter mile from Ogden Avenue to Douglas Drive.

8. Lakefront Trail (South of 18th Street)

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Soldier Field Sled Hill
Chicago, IL 60605

The biking and pedestrian paths have been separated over the last couple of years but the North Side of the Lakefront Trail is still crowded and treacherous—especially on the weekends. But if you start on the path just east of Soldier Field and go south, there are about 7 miles of relatively peaceful lakeside biking ahead.

9. Washington Park to Jackson Park

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Washington Park
Chicago, IL

This leafy 3-mile ride keeps you mostly in South Side parks near Hyde Park. You start in the western park of Washington Park through Ellsworth Drive and then head south on Morgan and Payne Drives. Then take a left on the chill Midway Plaisance and cruise through historic Jackson Park.

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Lunchtime views

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10. Major Taylor Trail

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Major Taylor Trail
Chicago, IL 60643
(312) 747-7661
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Named after legendary African American cyclist Marshall “Major” Taylor, this 6-mile trail is one the few car-free routes in the city. The trail goes from Dan Ryan Woods in the north to Whistler Woods in the south—connecting several neighborhoods on the city’s Southwest Side.

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1. North Shore Channel Trail

N Shore Channel Trail, Chicago, IL

This 6.7-mile path starts near Lawrence and Francisco and runs parallel to the North Shore Channel to Evanston. It will be even better once the construction of a 180-foot-long, bridge over the North Shore Channel is officially completed, allowing cyclists to avoid a Lincoln Avenue detour.

N Shore Channel Trail
Chicago, IL

2. West Berteau Avenue & North Lincoln Avenue

W Berteau Ave & N Lincoln Ave, Chicago, IL 60618
A tree-lined street with two parked cars and a painted bike line.
Bertreau Avenue near Clark Street
Google Street View

The city’s first Greenway project, this mile-long corridor that prioritizes non-motorized traffic, stretches from Clark Avenue to Lincoln along Berteau Avenue. It also serves to connect four other bike-friendly routes—Damen, Lincoln, Clark, and Southport.

W Berteau Ave & N Lincoln Ave
Chicago, IL 60618

3. The 606

Chicago, IL 60647

The 2.7-mile elevated Bloomingdale Trail, casually known as The 606, is a refreshingly car-free way to pass through some heavily trafficked Northwest Side neighborhoods—Bucktown, Logan Square, Humboldt Park.

4. Humboldt Park

Humboldt Park, Chicago, IL

The three big West Side parks, connected by formal boulevards and dotted with tranquil bodies of water, are great beginner spaces to bike around. Humboldt Park’s Luis Munoz Martin Drive is a great place loop to bike along. Just watch for the occasional alligator.

Humboldt Park
Chicago, IL

5. North Elston Avenue & North Milwaukee Avenue

N Elston Ave & N Milwaukee Ave, Chicago, IL 60642

Of all of the diagonal streets that defy Chicago’s famed grid system—Elston Avenue ranks the best for cyclists who want a low-stress route. The southern portion of the road especially (from its starting point on near Chicago Avenue to Webster Avenue) goes through emptier industrial corridors and features a 1.68-mile protected bike lane.

N Elston Ave & N Milwaukee Ave
Chicago, IL 60642

6. Northerly Island

1521 S Linn White Dr, Chicago, IL 60605
A wide concrete path with tall grass on either side. A biker in the distance is stopped gazing at the clouds at dusk.
Northerly Island path
Ryan Smith

The paved path on the southern tip of Northerly Island is a relatively short ride (less than a mile) but it’s a tranquil one filled with wildflowers and prairie grass, and beautiful views of the lake and city skyline. Be warned, it’s partially closed currently as the city repairs some of the concrete damaged by erosion.

1521 S Linn White Dr
Chicago, IL 60605

7. Douglas Park

1401 S Sacramento Dr, Chicago, IL 60623

Avoid it during Riot Fest, but otherwise Douglas Park is a pleasant park to explore on your bike. 

That’s especially true when you travel north on Sacramento Avenue using a curb-protected bike lane that stretches for a quarter mile from Ogden Avenue to Douglas Drive.

1401 S Sacramento Dr
Chicago, IL 60623

8. Lakefront Trail (South of 18th Street)

Soldier Field Sled Hill, Chicago, IL 60605

The biking and pedestrian paths have been separated over the last couple of years but the North Side of the Lakefront Trail is still crowded and treacherous—especially on the weekends. But if you start on the path just east of Soldier Field and go south, there are about 7 miles of relatively peaceful lakeside biking ahead.

Soldier Field Sled Hill
Chicago, IL 60605

9. Washington Park to Jackson Park

Washington Park, Chicago, IL

This leafy 3-mile ride keeps you mostly in South Side parks near Hyde Park. You start in the western park of Washington Park through Ellsworth Drive and then head south on Morgan and Payne Drives. Then take a left on the chill Midway Plaisance and cruise through historic Jackson Park.

Washington Park
Chicago, IL

10. Major Taylor Trail

Major Taylor Trail, Chicago, IL 60643

Named after legendary African American cyclist Marshall “Major” Taylor, this 6-mile trail is one the few car-free routes in the city. The trail goes from Dan Ryan Woods in the north to Whistler Woods in the south—connecting several neighborhoods on the city’s Southwest Side.

Major Taylor Trail
Chicago, IL 60643