Cycling in Chicago: 13 Challenging Bike Trails in Chicago That You Wouldn't Want to Miss!

Cycling is not just the sport for you to indulge in summers or spring, it is indeed an all-year-round sport. Chicago has biking trails for everyone, be it beginners or avid cyclists, and to top-it-off, you can bike any time of the year. 

Biking trails in Chicago are encircled with scenic vistas of the city, wooded settings to enjoy the native wildlife, and indulge in recreational activities like fishing or boating. Some bike trails also pass through famous spots of the city, with restaurants and shops nearby for the bikers to enjoy a short excursion on the way. Although challenging, Cycling in Chicago is sure to be a fun and thrilling experience. 

Explore the Top 13 Spots for Cycling in Chicago!

1. Deer Grove Forest Preserve Trails

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The Deep Grove is Cook County's first Forest Preserve that features 2000 acres of diverse habitat of rolling forests, wetlands, prairies, and wooded ravines. The trail system in Deep Grove is a network of paved and unpaved trails. Paved trails are for cyclists, cross-country skiers, and pedestrians, while the unpaved trails are for mountain bikers, hikers, and equestrians.
Address: W Dundee Rd, Palatine, IL 60067
Length of the trail: 15.5 miles
Trailheads: Deer Grove, Deer Grove-West, Deer Grove-East, Camp Alphonse
Difficulty level: Introductory to advanced

2. Green Bay Trail

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Paved with asphalt and crushed limestone, the Green Bay is a rail with trails that runs parallel to Metra's North line. It extends from Wilmette to Highland Park. As it is a multi-purpose trail, it is primarily used by cyclists, walking, inline skating, and more. Moreover, the Green Bay trail is just a mile away from Lake Michigan, for the visitors to enjoy the beachfront view.
Length of the trail: 9 miles
TrailHeads: Ravinia, Highland Park, Wilmette, Kenilworth, Indian Hill, Winnetka, Hubbard Woods, Glencoe, BraesideTrail end points: St. Johns Ave. at Sheridan Rd. (Highland Park) and Greenleaf Ave. (Wilmette)
Difficulty Level: Moderate

3. Busse Woods Trails

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Popularly known as the Ned Brown Preserve, the Busse Woods is a 3558-acre preserve making it one of the largest and diverse forest preserves in Cook County. The preserve features elk pastures, upland forests, miles of paved trails with fishing and boating areas. The miles of loop trails here are ideal for cyclists, hikers, pedestrians, etc. As Busse Woods houses varied bird species, visitors can spot these from the birdwatching hotspots along the trail.
Address: N Arlington Heights Rd, Elk Grove Village, IL 60007
Length of the trail: 11.2 Miles
Trail end points: Biesterfield Road and Golf Road (Ned Brown Forest Preserve)
Amenities: Portable bathrooms

4. North Shore Channel Trail

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The North Shore Channel Trail extends between the Green Bay junction and the Lawrence Avenue junction. Paved with asphalt, crushed limestone, and dirt makes it accessible to bikers, hikers, pedestrians. 
Address: W Argyle St & N Francisco Ave, Chicago, IL 60625
Length of the trail: 6.7 Miles
Trail End Points: Greenbay Rd. and Ronan Park at W. Ainslie St.
Trail type: Out and Back

5. Des Plaines River Trail

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The Des Plaines River Trail is a long-stretch of recreational multi-use trail that runs parallel to its namesake river. This trail is used primarily for biking, hiking/walking, cross-country skiing, and snowmobiling. Heavy rains make a section of this trail inaccessible, as it lies in the floodplain area of the Des River.

Visitors can enjoy the various wildlife and picturesque views as they meander across the trail path. The trail passes through numerous forest preserves, which provides additional recreational activities for the visitors like boating, fishing, etc.,
Length of the trail: 56.2 Miles
Trail endpoints: Van Patten Woods Forest Preserve entrance on Russell Road/County Road 19 (Wadsworth), and Jerome Huppert Woods Forest Preserve near IL 64 and IL 171 (River Grove)
Amenities: Public Parking, Toilets

6. Illinois Prairie Path

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Situated in DuPage County, the Illinois Prairie Path is a rail-trail that consists of a network of biking trails. The trail traverses into three branches, the northwestern, the southwest, and the eastern. The northwest branch or the Elgin branch runs over 15 miles to Elgin, the southwest branch or the Aurora Branch runs over 12 miles to RiverEdge Park, and the eastern branch or the main stem runs 14 miles to Forest Park. Both the northwest and southwest branches intersect at the Fox River Trail.

Paved with crushed stone, asphalt, and concrete makes it an ideal trail for biking, hiking, cross-country skiing, and more! Traveling through commercial areas, small forests, steep-hill climb the IPP trail is a challenge for bikers and one of the best spots for cycling in Chicago.
Address: 616 Delles Rd, Wheaton, IL 60187
Length of the trail: 61 Miles
Trail endpoints: Forest Park CTA Station at Van Buren St. (Forest Park) and spurs in Aurora, Batavia, Elgin, and Geneva that all end at points along the Fox River Trail

7. Salt Creek Trail

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Paved with asphalt, cinder, and woodchips, the Salt Creek Trail is cardinally used for biking, inline skating, walking, and is wheelchair accessible too. It is a network of paved and unpaved trails that run along Des River River, Brookfield Zoo, and Salt Creek. As the bikers meander across the trail path, they can enjoy bird watching, scenic views, or explore the Brookfield Zoo.
Length of the trail: 26.7 Miles
Trailhead: Bemis Woods-South, Brezina Woods, Bemis Woods-North, Brezina Woods, Twenty-Sixth Street Woods-West, Brookfield Woods, Cermak Woods, Stony Ford Canoe Landing, Chicago Portage National Historic Site.
Trail endpoints: McCormick Ave. (Brookfield) and Busse Woods Forest Preserve (Elk Grove Village)

8. Major Taylor Trail

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Named after a revered and skilled African-Ameican Bicycle racer, the Major Taylor Trail runs between Dan Ryan Woods and Whistler Woods. It is an asphalt paved trail that makes it perfect for cycling in Chicago with other activities like walking, inline skating, and cross-country skiing.
Address: 2198 W 83rd St Chicago IL 60620
Length of the trail: 7.6 Miles
Trailhead: Dan Ryan Woods-North, Dan Ryan Woods-Central, Dan Ryan Woods-91st Street, Whistler Woods
Trail endpoints: Dan Ryan Woods north of W. 83rd St. at S. Western Ave. (Chicago) and Whistler Woods north of W. 134th St. at S. Halsted St./SR 1 (Riverdale)
Trail type: Rolling

9. Cal-Sag Trail

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The Cal-Sag is an asphalt paved trail that runs between Sag Quarries and Burnham Greenway. This trail provides access to several forest areas and natural areas. This trail traverses through highways to wooded settings, making the Cal-Sag trail ideal for cycling and other recreational activities like fishing, birdwatching, etc.
Address: 7402 Lake Katherine Dr, Palos Heights, IL 60463
Length of the trail: 15 Miles
Trailhead: Sag Quarries, Teason's Woods, Cal-Sag Parking, Lake Katherine Nature Center, Freedom Park, Whistler Woods
Trail endpoints: John Husar I&M Canal Trail (Lemont) and Freedom Park (Alsip)

10. Lakefront Trail

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The Chicago Lakefront Trail runs along the shore of Lake Michigan. The trail is ideal for walking, hiking, skateboarding, jogging, cycling, which passes through several recreational amenities, beaches, and lakefront parks. There are several attractions along the path like the Soldier's Field, Navy Pier, the Museum of Science and industry, and more. Numerous beaches, parks, and attractions along the trail path make it an ideal spot for Cycling in Chicago.
Address: 540 N Lake Shore Dr, Chicago, IL 60611
Length of the trail: 18.5 Miles
Trailhead: Edgewater Beach/Lincoln Park (north) to South Shore/Jackson Park (south)
Trail endpoints: E. 71st. St. and S. South Shore Dr. (US 41) and W. Ardmore Ave. and N. Sheridan Road (Chicago)
Difficulty Level: Easy

11. Valley Line Trail

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Also known as Sauganash Trail, the Skokie Valley trail extends between Bryn Mawr Avenue and Devon Avenue. It is an asphalt paved trail with parking and bathroom facilities along the trail path.
Address: 5828 N Rogers Ave, Chicago, IL, US, 60646
Length of the trail: 1.1 Miles
Trail endpoints: W. Bryn Mawr Ave. just east of N. Kostner Ave. and W. Devon Avenue between N. Kostner Ave. and N. Kirkwood Ave.
Difficulty Level: Easy

12. North Branch Trail System

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The North Branch Trail System is a cardinal spot for Cycling in Chicago. A system of paved and unpaved trails that runs along the Chicago River. Near the north end of the North Branch System Trail trail are the Chicago Botanic gardens and the Green Bay Trail. Flanked by restaurants, residential neighborhoods, parks, the Green Bay Trail is just a mile away from Lake Michigan. If you are looking for a short excursion along the trail path, it is the perfect trail system for you!
Length of the trail: 21.3 Miles
Trail endpoints: Dundee Road and I-94 (Northbrook) and Foster Avenue west of Pulaski Road (Chicago)
Trail type: Flat, Rolling

13. Bloomingdale Trail or the 606

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Formerly a rail line, the 606 is now an elevated rail-trail in Cook County. As the trail passes through Logan Square, Wicker Park, Bucktown, Humboldt Park, it is thereby suitable not just for cyclists but for all. You can spot cyclists, pedestrians, people walking their dogs, children, even runners on this trail. The trail also has many coffee shops, parks, restaurants, bars, historical sites, and other places of interest along the trail route.
Address: 1600-3700 W Bloomingdale Ave, Chicago, IL 60647
Length of the trail: 2.7 Miles
Trail endpoints: Walsh Playground Park (N. Marshfield Ave. near W. Bloomingdale Ave.) and N. Ridgeway Ave. just south of W. Cortland St. (Chicago)
Amenities available: bike parking, no bathrooms

Tips for Cycling in Chicago!

Cycling in Chicago is a great way to explore the city. However, there are some modicum tips that every biker must take care of while riding!
  • Choose a bike trail that you are comfortable with!

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From shared lane markings to car-free zones, choose a bike trail that you are comfortable with or the one that commensurates with your skill level.
  • Follow the bike route, and do not ride on the sidewalk unless marked otherwise.

It is best to ride on the marked bike lanes for your safety and that of the pedestrians.
  • Don't ride with headphones on or use your phone

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Riding with headphones on or talking/texting on the phone poses a distraction hence, it is good to be vigilant at all times. 
  • Gestures work well while changing directions or speed

Pointing in the direction that your intent to go or a hand signal while changing speeds
  • Stay three feet away from parked cars

If there are no bike lanes or shared lane markings, keeping a safe distance of three feet will keep you away from parked cars. It prevents you from getting knocked out by a car door when opened suddenly.
  • Do a pre-bike ride check

A pre-bike ride check entails checking on the brakes, adjusting the seat, and checking the tires. 
  • Ride with the traffic and not against it!

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By law, bikers/cyclists must ride in the direction of the cars and not against it.
  • Practice extra caution and awareness where pedestrians are walking.

Ring the bell to make pedestrians aware of your presence, especially on the intersections and crosswalks.
  • Last but not the least-Wear a Helmet

Always wear a helmet while riding. Make sure it fits you perfectly, and don't forget to buckle the chin strap!

Chicago is known as the primary location for Cycling in the United States. Meandering across the city and running parallel to Lake Michigan and the Chicago River are these beautiful spots for Cycling in Chicago! Step out for a casual bike ride, or challenge yourself with the mountain bike rides as you pedal across these premier locations for Cycling in Chicago!

This post was published by Akshita Dhiman

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