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Chicago Bike Trails & Paths

Bicycle Trail Paths ChicagoRegardless of whether you are an experienced cyclist craving a challenge or simply enjoy the thought of taking in the scenery during a recreational ride, you may be surprised at just how accommodating Chicago and its suburbs have become to those looking to hit the trails. 

The City of Chicago was recently ranked as the fifth friendliest city in the country to bicyclists and the city plans to become even more attractive to cyclists over the next five years with the addition of over 600 additional miles of trails and street bike routes.

If you are looking to hit the trails but don’t know which trail is for you or where to begin, consider the following paths and trails located in or near the city.

The Chicago Lakefront Trail

If you want to avoid the streets of the city but still want to take in the sights, are a tourist looking for an exciting way to explore the city or just want to take a long distance ride along the lake, the Lakefront Trail is a wonderful place to begin. 

This trail spans roughly 18.5 miles and will lead travelers past numerous monuments and notable landmarks in the city. If you take a trip down this trail, you will be in riding distance of the following.

  • Numerous parks which include Lincoln Park, Grant Park and Jackson park. Lincoln Park is also renowned for its zoo, which attracts millions of visitors each year.
  • The Belmont and Monroe harbors and world famous Navy Pier. Navy Pier is home to many tourist attractions and host of events and activities that include boat rides, a gigantic Ferris wheel and Chicago’s Shakespeare Museum.
  • A multitude of museums and attractions that include the Shedd Aquarium, Museum of Science and Industry, Adler Planetarium, the Field Museum and Soldier Field— home of the Chicago Bears.
  • Access to several neighborhoods of repute that include Hyde Park, South Shore and Lake View.

The North Branch Trail

This beautiful trail allows city residents to access the sereneness and beauty of nature even though it is located in the center of a metropolis.

If you are looking for an escape from the noise and crowds and want to reconnect with nature, you should consider a ride along this 20 mile trail that follows a portion of the Chicago River and ends at the Chicago Botanical Garden at its northernmost point.

Other features riders have access to include the following.

  • Resting areas and public bathrooms for bicyclists that desire a pit stop or to take a break simply to take in the scenery.
  • Access to alternate dirt paths where visitors may choose to ride on horseback.
  • Connection to the Green Bay Trail for riders looking to extend their bike hikes.

The Green Bay Trail

This nine mile trail is an excellent extension option for long distance riders who don’t want to cut their experience short after the riding the North Branch Trail, but also has plenty to offer to the novice or recreational rider.

What gives this trail exceptional utility is that it runs parallel to the Metra commuter rail so that cyclists have the opportunity to travel as far north on the trail as they wish before having the option to take the rail home. 

Other features of this trail include the following.

  • Numerous restaurants, stores and community parks provide ample opportunity for riders to take a breather or to explore the beautiful neighborhoods they pass through.
  • This trail is child friendly and a great path for families to ride along together because of its vicinity to the rail and numerous locations where families can rest, eat and explore.
  • Access to the Metra should you feel too tired to ride back to where you began. Instead you can just hop onto the next train and relax.
  • Proximity to Ravinia, which includes an open air pavilion that is used for numerous live musical performances which include a diverse range of music genres.
  • The option to connect to the Robert McGlory Bike Path.

The Robert McGlory Bike Path

You may find that even those who know their way around Chicago are conflicted when asked where this trail is located because it has gone under numerous names in the past.

One of those names is the Green Bay Trail, which it connects to at its southern point. It is also known by many as the North Shore Bike Path, even though another path now exists by that name. 

If you travel along this 26.5 mile long trail to its end, it will take you all the way into Wisconsin.

Some of the most notable features of this trail include the following.

  • A route along the Chicago North Shore and Milwaukee railroad corridor, which is a famous stretch of railroad running from the north side of Chicago into Wisconsin. The old towers, electrical cables and notable landmarks that adorned the railroad are still intact and make up the majority of the scenery along this route.
  • Brief sections of trail that converge with city streets, providing a more urban feel and experience.
  • Community gardens bring beauty to great stretches of the trail and as you progress, the feel slowly moves from urban and industrial to the open country.
  • At the very end of the trail, the cityscape turns into prairies and fields before ending at a patch of forest.

The Illinois Prairie Path

If you want to experience history firsthand there is no greater way than to travel the famous 61 mile long Illinois Prairie Path, which runs along the route of historic railroads that have since been converted to paths.

There are numerous ways that you can choose to travel this path and it includes three main branches with a total of five connections, allowing you to travel the trail numerous times while having different experiences. 

The length of this trail suggests that it may be most appropriate if you are an experienced cyclist if you wish to ride its entire length. It may not be the best choice if bringing along children as the trail includes steep hills and drops.

  • Depending on the branch you choose to travel along, this trail stretches along urban streets and through the western suburbs on its main branch or through older neighborhoods, prairies and woodlands along its Aurora branch. Finally, the Elgin branch connects Wheaton and Elgin and features a mixture of forests and residential zones.
  • The main branch features gorgeous train depot houses that have been restored to provide a historic element to your journey. These historical landmarks also provide rest areas and access to water so that you can rest or fill up on water before continuing your bike hike.
  • If you travel the entire trail your experience will truly be diverse as the trail cuts through urban and rural areas, providing the perfect balance between immersion in nature and access to the suburbs.
  • The trail ends at Volunteer Park, which is the perfect place to end a 61 mile long trek as the park is located where three active rail lines converge. This affords you the opportunity to hop on a train and rest up on your way home if you so desire.

The Hennepin Canal Parkway

If you are looking for a rustic, urban and historical experience, this bike trail is worth exploring. The path features a 105 mile long canal that was quickly abandoned after it was built at the turn of the twentieth century to connect the Illinois River to the Mississippi. 

Most of the structures that accompanied the canal are still intact and it represents a unique piece of Chicago’s history— most notably how the railroads forced many other modes of transportation out of business. If you choose to ride this trail, consider the following.

  • This trail is suitable for most bikes but you will find it easiest to travel on a hybrid bike.
  • The path does not feature many hills and is consistently flat, making it an easier option if you wish to bring children along or are a novice cyclist.
  • You will need to pack water and snacks because there are few locations along this trail that provide access to food or drinks. On hot days, make sure that you stock up on water so that you and your group do not become dehydrated.
  • The best time to travel this path may be during the fall because it travels through a diverse backdrop of forest, prairie and farmland. You are also less likely to face severe heat during an autumn ride.

The Jane Addams Trail

If you have any appreciation for nature at all, you need to jump on the opportunity to travel this beautiful 15 mile long trail. It is also a wonderful bike path to ride if you want to travel with your family as it features densely wooded areas perfect for bird watching and populated with deer. 

Many educational field trips are conducted along this trail because of its immersion in a natural environment that is generally undisturbed by humanity. Keep the following in mind when traveling this trail so that you choose the right time and are aware of its key features.

  • The trail starts in Freeport and runs all the way into Wisconsin where it connects to the Badger State Trail. Unless you wish to continue on to Madison, the best place to end your trip is in Orangeville where you will have access to shelter, food and drinks so that you and your party can rest up.
  • The abundance of deer attracts hunters so the trail is closed during the fall for your safety. Keep this in mind when planning a bike hike on this path.
  • If you have the opportunity, you may want to visit the childhood home and burial site of Jane Addams, the philanthropist and Nobel Prize winner for whom the trail is named.
  • Environmental features include wild owls, hawks and other birds of prey as well as an array of four legged creatures that you can spot along the trail. You may run into deer as they are common in the area.
  • This trail connects you to both the Pecatonica Prairie Trail near Freeport and the Badger State Trail where it ends at the Wisconsin border.

The North Shore Channel Trail

For a shorter and easier ride you may want to consider the North Shore Channel Trail, which stretches 6.7 miles along the North Shore Channel and combines scenic nature with an urban landscape.

This trail has numerous branches that allow bicyclists of differing experience levels to enjoy themselves and many additional activities and landmarks can be accessed along its path. 

Those features include the following.

  • Dirt paths that lead into wooded areas for mountain bikers and more experienced cyclists.
  • A dock where travelers can choose to go canoeing or kayaking along the channel.
  • Mixed landscapes that include an urban industrial zone and several parks and wooded areas where bicyclists can connect with nature.
  • The option to incorporate city streets into your route or to cut down on the number of street crossings you come across by using the east side of the trail.
  • Playgrounds, parks and a baseball stadium which all provide amenities to make for a great family experience.

The Major Taylor Trail

If you desire a distinctly urban experience, this trail is perfect and it allows riders to explore areas south of the city rather than taking the northern routes afforded by most of the other trails in the city.

Just 7.2 miles long, this trail begins in the southwest side of Chicago and ends at the Little Calumet River where it connects to the Cal-Sag trail. Features of this trail include the following.

  • A purely industrial and urban feel that includes the opportunity to explore the southwestern areas of the city.
  • Parking at both ends of the trail so that travelers can easily access the trail.
  • Access to Bronzeville, home of Marshall “Major” Taylor, who was an African-American bicyclist who set the world record for the 1 mile sprint.

The Des Plaines River Trail

This 56 mile long trail is another option you should consider if you enjoy constantly changing scenery along your route that links suburbia with multiple forest preserves, parks and prairies.

The trail offers protection to a plethora of river animals, fish and lizards along the Des Plaines River. Its features include the following.

  • Numerous access points that allow bicyclists to park and enter the trail at their desired locations. This is great if you only wish to travel a portion of the trail rather than the entire 56 miles but also affords you the option to ride as far as you would like to.
  • Diversity of terrain that includes urban neighborhoods, rivers and lakes, forests containing an abundance of aged trees, lowlands and open fields.
  • Access to parks and forest preserves to take in the surroundings and rest up if you feel worn out.

The Millennium Trail

If you’ve already explored many of the existing trails throughout the Chicago area, you may want to add the Millennium Trail to your list. This trail is still under development and is expected to be 35 miles long upon completion, but over 28 miles are currently open and accessible to the public to enjoy.

The Millennium Trail begins in Lindenhurst and runs a southern route that passes by numerous historical landmarks and forms of terrain. The features include the following.

  • The Bonner Heritage Farm, which is a great place to bring children. This farm was settled in the middle of the nineteenth century by Scottish immigrants and currently provides children with an educational experience about how the farmers lived and produced food that includes interaction with barnyard animals.
  • The McDonald Woods Forest Preserve is one of the first features you encounter along this route and is the first of several forest preserves that include wetlands, lakes and gentle hills.
  • Open prairies and pastures that intertwine with tree groves to provide a mixture of cooling shade and open air throughout your ride.
  • Access to a frisbee golf course along the trail’s route which offers an opportunity for your family to rest while enjoying some recreation.
  • Access to the Lakewood Forest Preserve at the trail’s end. This preserve offers a nine mile horse path, fishing and picnic areas where you can take another break and enjoy a meal before beginning the journey back to where you began.

This guide provides only a glimpse at the trails available to bicyclists throughout the greater Chicago area and the City of Chicago has promised to add another 600 miles of paths over the next five years.

For more information about the paths available or how to get the most out of your biking experience; check with Divvy, which provides residents with access to bikes and maps so that they can hit the trails even if they do not currently own a bicycle. You may also find more information about the numerous trails throughout Illinois at

Historical Bicycle Routes

League of American Wheelman 1896 Ride

This route is based upon an originally published extract entitled "The League of American Wheelman 1896 Ride" – by the Bicycling Department, Volume XVII, Number 871 of Harper's Round Table. Originally published Tuesday, July 7, 1896 (original text as per publication together with spelling and grammatical representation of the original text extract):

The route given in the next three weeks will be one of the best trips in the vicinity of Chicago, extending from Chicago itself to Joliet, thence to Ottawa, and thence to La Salle, and return. Like the great majority of trips taken from Chicago, this one depends largely upon the time at the rider’s disposal, for you may either start from Chicago itself, or if the time is too short you can take the train for Ottawa and ride front there, or it is possible to get off the train at Joliet and ride on. But if time is not so important a matter, it is by all means best to ride all the way from Chicago. A choice of roads leads out of the city. You can go by the Archer Road to Joliet via Summit, Mount Forest, Willow Springs, Sag, Lentomt, Romeo, and Lockport. In going the other way, take the Washington Boulevard west to Des Plaines Avenue, and then south to Riverside. This route leads along the old Illinois-Michigan Canal, Des Plaines River, and the new drainage canal, and it gives an excellent opportunity for you to examine the work of this large engineering undertaking.

THERE IS STILL ONE OTHER ROUTE to Joliet, which is a good road if the weather is good, hut witich after rain it would be unwise to attempt. This route is as follows: Start south of Western Avenue, or go down through Pullman City, turningg westward to arrive at Blue Island. Here it will be necessary to make inquiry for the Blue Island and Orland Road, which runs south west through Orland Station on the Wabash railway to Joliet. Part of this secondary route is not on the map, but it can be traced from Orland through Alpine, Hadley, and on into Joliet.

The most attractive route, however, is the second one—that , through Riverside, Suemmit, Willow Springs, etc.

ON THIS FIRST STAGE TO JOLIET the road to Summit is easily found, except that on passing through Stimmit a sharp turn to the left should be made, instead of crossing the track and the canal, up a hill, the road then being perfectly clear through Mount Forest and Willow Springs to Sag Station, with one hill about midway betweett the two latter places. At Sag Station turn to the left and run down to Sag, less than a mile away; then, turning sharply to the right, run to Lockport. Tnence, keeping always on the southern and eastern side of the tracks and the river, follow the road to Romeo, with a hill as you enter the town, and run tnence through Lockport to Joliet. The distance is close upon forty miles. If the trip is made in a day, a good place to stop is at Sag. If however, the wheelman decides to run to Ottawa in one day, Joliet would make a stop a little less thact half the distance; though this run to Ottawa of about ninty miles is a little too much for the average rider, and Joliet being a good place to stop overnight, he is advised to make a two days' trip of the journey. In case Joliet is too far, there is a good hotel at Lockport, six or seven miles nearer Chicago than Joliet, and the stop might be made there, although that leaves a long ride for the next day.

Harper & Brothers, 1896. Harper's Round Table, Volume 17 p. 1128 Published July 7, 1896
See this link for original publication

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