May 9, 2023

8 Best Running Trails in Chicago

By Rahul Malpe
8 Best Running Trails in Chicago

Let's face it: running can be a love-hate relationship. But when you stumble upon that dreamy trail with breathtaking vistas and pitch-perfect terrain, it morphs into a full-blown love affair.

If you're in Chicago or planning a visit, we've got some fantastic news: the Windy City is home to an amazing running scene that's as diverse and vibrant as the city itself. 

From a bustling runners' community to thrilling events and clubs, Chicago flaunts a one-of-a-kind cityscape and landscape that'll have you swooning over running anew.

So, strap on those sneaks, and let's explore the 8 top running trails in Chicago, guaranteed to make your heart race.

1. Lakefront Trail

Shutterstock - Woman running along Lake Shore

If you're craving a run with a view, look no further than the legendary Lakefront Trail.

Spanning 18 miles, this paved gem weaves alongside Lake Michigan's shores, flaunting unbeatable panoramas of the city's skyline and the majestic, shimmering lake. No shocker, then, that it's the go-to for Windy City locals and out-of-towners alike!

As you jog, you'll breeze by hotspots like the Navy Pier, Museum Campus, and a bunch of sandy beaches, perfect for a sightseeing spree while getting your heart rate up.

Word to the wise: The trail can be a bit of a squeeze during rush hour. So, if you're after a more tranquil vibe, lace up your sneakers for an early morning or late evening jaunt.

2. North Branch Trail

Craving a bit of nature in the midst of the bustling city? The North Branch Trail is your answer. 

This 20-mile long, mostly paved trail takes you along the North Branch of the Chicago River and through lush forests and picturesque parks. 

It's an ideal escape for those looking to soak up some tranquility while clocking in the miles. 

The trail also connects to the Chicago Botanic Garden, where you can take a well-deserved break and admire the beauty of the gardens before continuing your run.

3. The 606 (Bloomingdale Trail)

In search of an urban trail with a twist? Say hello to The 606, also fondly known as the Bloomingdale Trail.

Built on a repurposed elevated rail line, this 2.7-mile ribbon of greenery and trail offers up a one-of-a-kind peek at Chicago's neighborhoods, art installations, and lush oases.

Brightly lit and bustling with runners, cyclists, and strolling folks, it's the perfect spot for mingling and people-gazing. 

Just a heads-up: The trail can get a bit packed, so time your run to dodge the crowds.

4. Waterfall Glen Forest Preserve

Located just outside of Chicago in suburban Darien, the Waterfall Glen Forest Preserve is a tucked-away treasure offering an invigorating run that's worth every step.

The 9.5-mile loop trail serves up a flavorful mix of terrain, from crushed limestone to dirt and grass, and boasts rolling hills that'll keep your legs on their toes.

Be sure to pause at the picture-perfect waterfall (yep, there's an actual waterfall!) and soak in the rich tapestry of plants and critters that call this charming spot home.

5. Busse Woods (Ned Brown Forest Preserve)

Prepare to have your breath taken away by the enchanting Busse Woods, a vast forest preserve nestled in Elk Grove Village, a short drive from Chicago.

The 11-mile paved loop trail guides you through dense woodlands, tranquil meadows, and along the Busse Reservoir's edges, where you might just catch a glimpse of a grazing elk herd in their special enclosure.

This peaceful oasis is the ideal setting for leisurely strolls or lengthy runs, with Mother Nature's finest as your backdrop.

6. Palos Trail System

For the adventurous souls seeking a wilder running escapade, the Palos Trail System in the southwestern 'burbs is calling your name.

Boasting over 40 miles of trails, from broad and breezy to slim and technical, Palos has got something to tickle every runner's fancy.

The paths meander through thick forests, skirting picturesque lakes and undulating hills, ensuring an exhilarating and gratifying workout. 

Keep your eyes peeled for mountain bikers and equestrians, as this trail network is a magnet for outdoorsy folks of all stripes.

And remember, don't miss out on the stunning views from atop Swallow Cliff, one of the region's most famous features.

7. Chicago Riverwalk

If you are craving a dash of city vibes during your run. You can't go wrong with the Chicago Riverwalk.

This 1.25-mile pedestrian promenade hugs the Chicago River, showcasing beautiful sights of the city's architectural marvels and those legendary moveable bridges.

With an eclectic mix of eateries, bars, and public art installations, the Riverwalk guarantees a vibrant, captivating route for runners.

Though the stretch may be on the shorter side, you can effortlessly lengthen your run by hopping onto the Lakefront Trail or venturing into downtown Chicago's bustling streets.

8. Des Plaines River Trail

And finally, the Des Plaines River Trail is a picturesque and calming retreat from city life's whirlwind pace.

Spanning over 50 miles through the forest preserves of Cook and Lake counties, this predominantly crushed limestone trail invites you for a soothing run beside the meandering Des Plaines River.

Well-kept and dotted with multiple entry points, it's a breeze to customize your run to the perfect length. And while you're at it, stay on the lookout for deer, birds, and other creatures that inhabit this lovely haven.

Tips for Running in Chicago

As you set out to conquer the finest running trails in Chicago, don't forget to arm yourself with some practical tips to elevate your experience and stay secure. 

Whether you're a running pro or just finding your stride, these useful nuggets of wisdom will have you geared up and eager to take on Windy City's eclectic running landscape. 

So, without further ado, here are our top tips for running like a champ in Chicago!

Running in Different Weather Conditions

Chicago's fickle weather may throw a curveball or two at runners, but with a dash of planning, you'll be mastering the elements like a champ.

During the chilly season, wear multiple layers and choose moisture-wicking materials to keep toasty and dry. Watch out for slippery ice patches and skip running in heavy snowfall. 

When summer heat waves hit, drink plenty of water and wear light-colored, breathable attire to stay fresh.

Sunscreen is a must! If it rains, a high-quality, lightweight rain jacket and shoes with a solid grip will make a world of difference.

Safety Tips for Urban Running

Hitting the pavement in a bustling city like Chicago brings a unique set of safety factors to mind.

Keep your wits about you, particularly when dashing through less crowded spots or after the sun sets. Tagging along with a pal or a crew not only amps up your safety but makes your run a blast.

Opt for well-lit, frequented trails when you can, and be sure to give a heads-up to someone about your planned route and estimated time of arrival back home.

Making the Most of Your Run

To truly relish your Chicago running escapade, plan out your route beforehand to dodge any disorientation or unforeseen hurdles.

Sprinkle in some interval training and hill drills to boost your stamina and power.

Above all, immerse yourself in the picturesque sights and dynamic vibes of Chicago's multifaceted neighborhoods and natural wonders.

Warm-up and Cool-down

To sidestep injuries and boost your running prowess, always remember to warm up before hitting the pavement and cool down once you've crossed the finish line.

Kick off your pre-run prep with dynamic stretches, like leg swings, arm circles, or hip rotations, to limber up those muscles and joints.

Once you've wrapped up your run, take a moment for some static stretches that focus on essential muscle groups — think hamstrings, quads, and calves — to help with recovery and keep muscle stiffness at bay.

Stay Aware of Bike Traffic

Chicago's beloved running trails often double as cyclist hotspots. So, keep your senses sharp and be ready to share the path.

Stick to the trail's right side, and if you're running with a pack, line up single file when bikes whizz by.

Give a wave or a shout to chat with cyclists and fellow runners, and always be ready to step aside when needed.

Use Running Apps and Websites

Running apps and websites like Strava, MapMyRun, and AllTrails can be invaluable tools for discovering new trails, tracking your progress, and connecting with other runners. 

They can also help you plan your routes, measure distances, and stay motivated by participating in challenges or virtual races.

Join a Running Club or Group:

Chicago's got a buzzing running scene, and hopping on board with a local running club or group is a fabulous way to link up with kindred spirits, keep your motivation high, and unearth fresh trails.

Some fan-favorite clubs are the Chicago Area Runners Association (CARA), Three Run Two, and our closely connected partner, the Family Style Run Club which fosters a strong sense of community among its members.

These clubs dish out group runs, tailored training programs, and lively social events that cater to a whole spectrum of experience levels. So, lace up and dive into the camaraderie!

Participate in Local Races

From the globally celebrated Chicago Marathon to quaint neighborhood 5Ks, lots of running events pepper the calendar to keep you inspired and pushing your limits.

Joining in on local races is a fantastic opportunity to immerse yourself in the city's dynamic running community, set your own milestones, and lend a helping hand to local charities and organizations. 


Chicago's running trails offer a little something for everyone, from serene escapes to bustling urban adventures. With such a diverse array of options, you will surely find the perfect trail that sparks joy in your running routine. 

So, what are you waiting for? It's time to hit the pavement and explore the best running trails Chicago has to offer. Happy running!

By Rahul Malpe

Rahul is a dedicated nutritionist and personal trainer with expertise in the science of nutrition and its impact on the body. Certified by the International Sports Sciences Association (ISSA) and the American Council of Exercise (ACE), he is committed to educating individuals through sharing science-based information on making smart food choices. By writing informative articles, Rahul aims to empower people with the knowledge they need to make informed decisions about their health and wellness journeys.