The Best Running Routes in Chicago

Cyclists, runners and walkers on Chicagos gorgeous trail, The 606.
Cyclists, runners and walkers on Chicago's gorgeous trail, The 606. | © Colin Hinkle / Courtesy of The Trust for Public Land

Chicago is a great place for joggers and runners, with beautiful, functional and convenient routes all across the city, getting you away from busy streets and constant red lights. While it definitely takes dedication to keep up with your routine during the long Chicago winter, knowing the city’s best trails, paths and parks can certainly help year-round.

The Lakefront Trail

The Lakefront Trail | © rlobes/Pixabay
© rlobes/Pixabay

The Lakefront Trail

There are many reasons to run on the Lakefront Trail: the great views of the lake and city, the calm and peaceful atmosphere, the fresh air, and the motivation brought about by sharing the trail with many other runners and cyclists. Stretching for over 18 miles (28.9 kilometers) from Edgewater to South Shore, mile markers make it perfect for tracking both short and long distance runs, and it’s so long that you can mix up which sections you use each time.

The Lakefront Trail, Chicago, IL, USA, +1 312 742 7529

The Lakefront Trail | © rlobes / Pixabay

Northerly Island

Museum, Park

Taking a diversion off the Lakefront Trail at Museum Campus, Northerly Island is a man-made peninsula featuring a number of paths for walking and running. Despite its proximity to the city, the 91-acre space is quiet and dedicated to nature, offering a more pleasant environment for your run if you want to get away from the city.

The 606

Hiking Trail, Park

The 606
© Colin Hinkle / Courtesy of The Trust for Public Land
Created specifically for walkers, runners and cyclists, The 606 is a multi-use trail and urban garden built on an old elevated train line. Alongside great views, manicured gardens and public art, useful features of the trail for runners include distance markers and soft surface paths. At 2.7 miles (4.3 kilometers) long, it’s fairly short, but there’s plenty to see to keep things entertaining on multiple journeys.

North Shore Channel Trail

North Shore Channel Trail

The North Shore Channel Trail is quieter than many of these routes due to its location further out of the city, and there are many other reasons to try it. Starting in Ravenswood and running all the way to Evanston, 6.7 miles (10.8 kilometers) in total, woodland-surrounded sections of the path provide shelter from both the sun and the wind, and there are plenty of water fountains in parks along the way.

North Shore Channel Trail, Chicago, IL, USA

Chicago Riverwalk

Park, Architectural Landmark

Looking down onto the Riverwalk in downtown Chicago on a warm summer day.
© D Guest Smith / Alamy Stock Photo

Designed more with relaxing tourists in mind, the Riverwalk nevertheless can be an amazing place to run, surrounded by some of the city’s most iconic buildings and the flowing Chicago River. There may be pedestrian traffic at times, but it’s almost always better than the crowds, traffic and red lights on the busy streets above.

Lincoln Park

Park, Zoo

Lincoln Park has everything—beaches, harbors, ponds, gardens, city views, and plenty of paths for runners to see it all while getting their sweat on. You can even make your run extra fun by taking a diversion through the free Lincoln Park Zoo, not an option that runners in many cities have available to them.

Humboldt Park


Just a couple of blocks south of The 606 in the up-and-coming neighborhood of the same name, Humboldt Park is a great option for extending your run. The huge 219-acre park has an inland beach and historic lagoons, with many paths and trails to get a good workout on while enjoying the scenery.
culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider


women sitting on iceberg


2 years.


It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.


I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air


Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.


Holiday Sale Offers on Our Trips

Incredible Savings

Edit article