The Best Hiking Near Chicago (That Won't Bore You to Death)

Look, I'll be honest—when I first moved to Chicago, I thought "hiking" meant walking to the L station. The city doesn't exactly scream "outdoor adventure." But after five years of exploring every forest preserve, state park, and random trail within driving distance, I've learned something: Chicago's hiking scene is actually pretty damn good. You just have to know where to look.

This isn't one of those exhaustive guides with 47 bullet points and a color-coded spreadsheet. I'm just going to tell you about the seven trails I actually go back to, what makes them worth your time, and which ones to skip if you hate crowds (spoiler: avoid Starved Rock on fall weekends unless you enjoy hiking in a conga line).

One thing I learned the hard way: the right gear makes a massive difference, especially when Chicago weather decides to swing 30 degrees in an afternoon. After years of trial and error, I've settled on merino wool clothing for most of my hiking—it regulates temperature, doesn't stink after multiple wears, and works year-round. If you're building out your hiking wardrobe, check out our men's merino wool base layer collection for versatile pieces that actually hold up on the trail.

 

How to Use This Guide

Here's how this works: I've got detailed write-ups on each trail below, but if you just want the quick version, check the trail picker table. It'll tell you which hike matches what you're looking for—easy morning walk vs. all-day challenge, good for kids vs. better solo, that kind of thing.

There's also a section specifically for families, dogs, and mixed groups because hiking with a toddler is very different from hiking solo, and not every trail allows dogs.

If you're worried about safety or what to pack, I've got sections on that too. Basically, everything I wish someone had told me before I showed up to Starved Rock in January wearing sneakers like an idiot.

Quick Trail Picker

Okay, here's the fast version. Pick what matters most to you and I'll tell you where to go:

What You Want	Best Trail	Drive Time	Why
Quick escape, super easy	Busse Woods	30 min	Flat, paved, perfect for an hour outside
Easy but actually scenic	Waterfall Glen	45 min	Nice 9.5-mile loop, quiet, works year-round
Family-friendly	Indiana Dunes	1 hour	Beach + dunes, kids love it, not too hard
Moderate challenge	Starved Rock	1.5 hours	Canyons and waterfalls, worth the hype
Serious workout	Devil's Lake	3.5 hours	Steep, rocky, actual climbing involved
Good with dogs	Indiana Dunes or Busse Woods	1 hour / 30 min	Both allow dogs, plenty of space
Fall colors	Palos Trail System	45 min	Gorgeous in October, lots of tree variety
Winter hiking	Waterfall Glen	45 min	Less crowded, still accessible, pretty in snow

If you're short on time: Busse Woods or Cook County preserves (15-30 min away)
 If you want a full day: Starved Rock or Devil's Lake
 If you've never hiked before: Start with Waterfall Glen or Busse Woods

7 Best Hike Trails Near Chicago

Starved Rock State Park

Drive: 1.5 hours southwest
 Difficulty: Moderate
 Distance: 13 miles of trails (you pick your route)
 Best Season: Spring for waterfalls, fall for colors

This is the one everyone talks about, and yeah, it lives up to the hype. Thirteen miles of trails wind through sandstone canyons with actual waterfalls—not the sad trickle kind, but legitimate waterfalls, especially in early spring when the snow melts.

The French Canyon trail is probably the best bang for your buck: 1.5 miles, decent workout, gorgeous rock formations. St. Louis Canyon is prettier but gets absolutely mobbed on weekends.

When to go: Early spring for waterfalls (March-April), or fall for colors but—and I cannot stress this enough—get there before 8am on weekends or you'll be parking half a mile away and standing in line to take photos.

Real talk: I once went on a Saturday in October at 11am. Took me 20 minutes to find parking, and the trails looked like Michigan Avenue during Christmas. Go early or go on a random Tuesday.

Winter warning: The canyons get icy and some have stairs/ladders. I slipped on my ass more than once before I learned to bring traction gear.

Indiana Dunes National Park

Drive: 1 hour east
 Difficulty: Easy to moderate
 Distance: 50+ miles of trails (most are short)
 Best Season: Summer

This place surprised me. It's a national park an hour from Chicago, and somehow it's not overrun every single day. You get Lake Michigan views, massive sand dunes, and forests all in one spot. The 3 Dune Challenge is fun if you want your legs to hate you—it's steep, sandy, and feels like climbing a mountain made of quicksand.

For an easier time, the Dune Ridge Trail gives you lake views without the quad-burning climbs. Summer weekends get busy, but nothing like Starved Rock. Just show up before 10am to snag decent parking.

Heads up: The dunes are beautiful but walking in sand is exhausting. What feels like a casual 2-mile hike will leave you more tired than you'd expect.

Good for: Families, dogs (on designated trails), anyone who wants beach + hiking in one trip

Waterfall Glen Forest Preserve

Drive: 45 minutes west
 Difficulty: Easy
 Distance: 9.5-mile loop (can do shorter sections)
 Best Season: Year-round (great after rain)

This is my go-to when I want to zone out for a few hours without committing to a whole day trip. It's a 9.5-mile loop around a ravine, mostly flat, mostly empty. The "waterfall" is more like an enthusiastic stream, but after rain it actually looks decent.

I've done this loop probably 30 times. It's perfect for clearing your head, and you can easily do half the loop if 9.5 miles sounds like torture. The crushed limestone path is smooth enough that I've seen people with strollers out there.

Best time: After it rains. Otherwise the waterfall is pretty underwhelming.

Good for: Beginners, families, people who want a longer walk without difficulty, accessible for mixed abilities

Palos Trail System

Drive: 45 minutes southwest
 Difficulty: Moderate to hard (depends on route)
 Distance: 40+ miles of interconnected trails
 Best Season: Fall

Palos is massive—over 40 miles of trails weaving through woods and marshland. It's great if you want options and don't mind figuring out where the hell you are. I've gotten turned around here more than once because the trail markers are...optimistic.

Fall is peak Palos season. The colors are stunning and the weather's perfect for longer hikes. Just download a trail map before you go because cell service is spotty and those wooden trail markers will absolutely lie to you.

Pro tip: The Cal-Sag Trail is the easiest loop if you're just testing it out. Save the full network for when you're feeling adventurous and have a GPS.

Good for: Experienced hikers who want variety and don't mind navigating

Busse Woods

Drive: 30 minutes northwest
 Difficulty: Extremely easy
 Distance: 7.2-mile loop
 Best Season: Year-round

This is not a challenging hike. The 7.2-mile loop around the lake is almost completely flat and half of it is paved. But you know what? Sometimes you just want to walk around a pretty lake without thinking too hard about it.

I bring my dog here constantly. It's crowded on nice weekends but midweek mornings are quiet. Good for families, good for people just getting into hiking, good for when you want to be outside but don't want to commit to anything serious.

Good for: Dogs, families with young kids, beginners, anyone who wants easy and close

Devil's Lake State Park

Drive: 3.5-4 hours north (Wisconsin)
 Difficulty: Hard
 Distance: 29 miles of trails (varies by route)
 Best Season: Summer

Okay, this one's a commitment. It's almost four hours away in Wisconsin, but if you want a real hike—steep climbs, rocky terrain, panoramic lake views—this is it. The East Bluff Trail will kick your ass in the best way.

I did this last summer and my legs were jelly for two days. But standing at the top looking out over the lake? Worth every burning quad muscle. This isn't a "let's casually go for a hike" place. This is a "we're making a weekend of it" destination.

Fair warning: Some trails are genuinely steep and rocky. Bring water, bring snacks, and don't attempt this in 90-degree heat like I did. Learn from my mistakes.

Good for: Experienced hikers, adventure seekers, people who want a challenge

Cook County Forest Preserves

Drive: 15-30 minutes (varies by location)
 Difficulty: Easy
 Distance: Multiple short trails (1-3 miles each)
 Best Season: Year-round

This is the catch-all category—dozens of small preserves scattered around the Chicago area. Most trails are short (1-3 miles), flat, and perfect for quick afternoon walks. They're not going to blow your mind, but they're accessible and everywhere.

I hit these up when I want to get outside but don't feel like driving an hour. Deer Grove and Cap Sauers are solid options. They're also great for dog walking since the trails are wide and easy to navigate.

Good for: Quick escapes, families, dogs, beginners, anyone close to the city

Hiking with Kids, Dogs & Mixed Groups

Taking Kids Hiking

Look, I'm not going to pretend hiking with small kids is relaxing. But some trails make it way easier than others.

Best trails for young kids (under 8):

• Busse Woods - Flat, paved sections, lake views keep them interested. The loop is long but you can bail whenever. I've seen kids on scooters here.
• Waterfall Glen - The "waterfall" (generous term) is exciting for little ones, crushed limestone is stroller-friendly, and you can turn around whenever they start melting down.
• Indiana Dunes - Kids love climbing sand dunes. It tires them out fast, which is basically the goal. Plus, there's a beach if you need a backup plan.

What actually works with kids:

• Bring way more snacks than you think you need
• Let them set the pace (or you'll just be carrying them)
• Turn it into a game—scavenger hunts, counting birds, whatever keeps them moving
• Have a backup plan for when they inevitably say "I'm done" after 15 minutes

If you're new to this, our complete guide to hiking with toddlers has more specific tips on gear and managing meltdowns on the trail.

Skip these with young kids:

• Starved Rock (stairs, ladders, steep drops)
• Devil's Lake (too challenging)
• Palos (easy to get lost, not much to keep kids engaged)

Hiking with Dogs

Most trails around Chicago allow dogs, but leash rules vary and some trails ban them entirely.

Best dog-friendly trails:

• Indiana Dunes - Designated dog trails, beach access (dogs allowed on some beaches), plenty of space. My dog loves the sand.
• Busse Woods - Wide trails, lots of other dogs, easy terrain. Just clean up after them.
• Cook County Forest Preserves - Most allow dogs, trails are wide enough that you won't be fighting for space.

Dog etiquette (because apparently this needs to be said):

• Keep them leashed (even if they're "friendly")
• Pick up their shit. Every time. No exceptions.
• Move to the side if someone's passing
• Not all dogs (or people) want to meet your dog—read the room

Check before you go: Some trails at Starved Rock and Waterfall Glen have dog restrictions. Look it up or you'll drive an hour just to turn around. Our guide to hiking with dogs covers trail etiquette and what gear actually helps.

Mixed-Ability Groups

If you're hiking with people who have different fitness levels or mobility issues:

Best accessible options:

• Waterfall Glen - Crushed limestone trail, mostly flat, smooth surface works for wheelchairs and walkers
• Busse Woods - Paved sections, completely flat, easy for everyone
• Cook County preserves - Many have paved or well-maintained trails

What helps:

• Pick the easiest option in the group—you can always add more distance
• Choose trails with multiple bailout points (loops are great for this)
• Check trail surfaces beforehand (paved > crushed limestone > dirt > rocky)

What to Pack 

I've learned this the hard way: you don't need to pack like you're summiting Everest for a 5-mile hike in Illinois. But you do need a few things.

Every single hike:

• Water - More than you think. I bring 1.5 liters for anything over 5 miles.
• Snacks - Your blood sugar will tank and you'll hate everything. Bring granola bars or whatever.
• Phone - For GPS, emergencies, and photos. Download offline maps.
• Decent shoes - Blisters will ruin your day. Trail runners work for most of these trails.

Add for moderate/hard hikes:

• Small first aid kit (bandaids, blister treatment, pain meds)
• Extra layer (weather changes fast)
• Headlamp if you might be out past sunset

Seasonal additions:

Spring (March-May):

• Waterproof boots (trails are muddy as hell)
• Rain jacket
• Extra socks (your feet will get wet at Waterfall Glen)

Summer (June-August):

• Sunscreen (you will burn)
• Hat
• Bug spray (mosquitoes at Palos are brutal)
• More water than you think

Fall (September-November):

• Light jacket (mornings are cold, afternoons are warm)
• Layers you can remove
• Check if it's hunting season at some preserves

Winter (December-February):

• Warm layers (merino wool or synthetic, not cotton)
• Waterproof insulated boots
• Traction devices for icy trails (microspikes or similar)
• Hand warmers
• Extra layers in your car in case something goes wrong

Need more detail? Our complete winter hiking gear guide breaks down exactly what to wear in different temperature ranges.

Clothing that actually works:

I'm not going to pretend there's one perfect outfit, but after years of trial and error:

• Avoid cotton - It gets wet from sweat, stays wet, makes you cold. This is how you get hypothermia on a 40-degree day.
• Merino wool is legit - Doesn't stink, regulates temperature, works in all seasons. Yeah it's expensive, but it's worth it if you hike regularly. If you're curious about the hype, here's why merino wool works so well for hiking. For specific pieces I actually use, the lightweight merino hiking shirt and merino hiking socks are solid starting points.

• Layer in winter - Base layer, insulating layer, waterproof outer layer. You'll be warmer than one giant puffy coat. Check out our guide to layering for cold weather hiking if you want the full breakdown.

•  

But honestly? Wear what's comfortable and weather-appropriate. You'll figure out what works for you.

Safety, Weather & Trail Etiquette

Chicago Weather Is Bipolar

One minute it's 65 and sunny, the next it's 40 and pouring. Chicago weather will lie to you. Here's what actually happens:

Spring: Trails are muddy, weather swings 30 degrees in a day. Waterfall Glen and Starved Rock turn into mud pits. Bring waterproof boots or accept soggy feet.

Summer: Hot, humid, thunderstorms appear out of nowhere. Check radar before you go. If you hear thunder, get off the trail—trees and lightning don't mix.

Fall: Perfect hiking weather... until it's not. October can be 70 or 40. Check the forecast and bring layers.

Winter: Trails get icy, especially at Starved Rock where the canyons turn into ice rinks. I've seen people sliding down on their asses. Bring traction devices or skip the steep trails.

Always check the forecast. Seriously. I've been caught in storms at Palos because I didn't bother looking. It sucked.

Actual Safety Issues

Most of these trails are pretty safe, but shit can still go wrong:

Icy trails (winter):

• High risk at Starved Rock, Devil's Lake
• Get microspikes or YakTrax ($30, totally worth it)
• Skip steep trails if it's been icy—not worth a broken ankle

Getting lost:

• Happens more than you'd think at Palos
• Download offline maps (AllTrails works great)
• Tell someone where you're going
• Bring a portable charger

Wildlife:

• Mostly deer, squirrels, occasional coyotes
• Not really dangerous but don't approach them
• Store food properly, especially if you're camping nearby

Weather turning:

• Lightning at Indiana Dunes near the beach is no joke—get to your car
• Hypothermia is a real risk in winter if you get wet and cold
• Heat exhaustion in summer—bring more water than you think

Crowds (yes, really):

• Starved Rock on fall weekends is genuinely dangerous—narrow trails, cliffs, tons of people
• Go early or pick a different trail

Trail Etiquette (Don't Be That Person)

Right of way:

• Hikers going uphill have right of way
• Step aside on narrow trails to let people pass
• Bikes yield to hikers (but be nice about it)

Noise:

• Don't blast music. Nobody wants to hear your playlist.
• Keep conversations at reasonable volume
• This is nature, not your living room

Dogs:

• Leash them. Always. "He's friendly!" isn't an excuse.
• Pick up their poop. Every time. I don't care if you're on a remote trail.
• Not everyone likes dogs—control yours

Leave No Trace:

• Pack out everything you bring in
• Don't leave trash "next to" the trash can because it's full
• Stay on marked trails (don't cut switchbacks)
• Don't pick flowers or mess with wildlife

Photos:

• Don't block the trail for your Instagram shot
• Be aware of people waiting behind you
• Starved Rock on weekends is basically a photo shoot—move along

Sample Itineraries

One-Day Southwest Loop

If you've got a Saturday and want to hit two good trails without driving all over:

Morning: Palos Trail System (45 min from Chicago)

• Start at the Cal-Sag Trail entrance around 8am
• Do the 7-mile easy loop (about 2-3 hours)
• Lake views, forest trails, nice variety

Afternoon: Waterfall Glen (15 min from Palos)

• Grab lunch on the way
• Hit Waterfall Glen around 1pm
• Do the full 9.5-mile loop or a shorter section
• Check out the waterfall (better if it rained recently)

Evening:

• Dinner in Oak Brook or Palos Hills
• Back in Chicago by 7pm

Total drive time: About 2 hours round trip
 Total hiking: 10-16 miles depending on your pace

Weekend Adventure (Two Days)

I did this last year with a friend. Worked out pretty well:

Saturday:

• Morning: Leave Chicago by 7am, get to Starved Rock by 8:30am
• 9am-12pm: Hike French Canyon, St. Louis Canyon, maybe Wildcat Canyon (4-6 miles total)
• Lunch: Town of Utica has decent food
• Afternoon: Drive 10 minutes to Matthiessen State Park (next to Starved Rock)
• 2pm-4pm: Hike the Dells Canyon area, more canyons and streams (2-3 miles)
• Evening: Stay overnight nearby (Utica or Peru have hotels)

Sunday:

• Morning: Drive to Indiana Dunes (1 hour from Starved Rock)
• 9am-12pm: Do the 3 Dune Challenge, then hit the beach or Dune Ridge Trail
• Afternoon: Lunch near the dunes, drive back to Chicago (1 hour)

Total: About 10-12 miles of hiking over two days. Doable if you're in decent shape and don't mind driving.

Honest assessment: Your legs will be tired by Sunday afternoon. Pace yourself Saturday so you're not destroyed for day two.

Quick Weekday Escape (3-4 hours total)

When you work from home and need to get outside:

Option 1: Waterfall Glen (45 min drive)

• Leave at 9am, there by 9:45am
• Hike 4-5 miles (half the loop)
• Back in Chicago by 1pm

Option 2: Busse Woods (30 min drive)

• Leave at 10am, there by 10:30am
• Do the full 7.2-mile loop
• Back in Chicago by 2pm

Option 3: Cook County Preserve (15-20 min)

• Any preserve near you
• 1-2 hour walk
• Home for lunch

 

Seasonal Guide (What's Actually Good When)

March-April (Early Spring):

• Best: Starved Rock (waterfalls are flowing)
• Also good: Waterfall Glen after rain
• Skip: Palos (muddy mess), Devil's Lake (might still have ice)
• Watch out for: Mud everywhere, unpredictable weather

May-June (Late Spring/Early Summer):

• Best: Indiana Dunes, Waterfall Glen
• Also good: Pretty much anywhere
• Skip: Nothing really, this is prime hiking season
• Watch out for: Ticks starting to appear, some trails getting buggy

July-August (Summer):

• Best: Indiana Dunes (beach access!), Devil's Lake
• Also good: Early morning hikes anywhere before it gets hot
• Skip: Starved Rock midday (hot, exposed trails)
• Watch out for: Heat, humidity, mosquitoes at Palos, crowds at popular spots

September-October (Fall):

• Best: Starved Rock, Palos (colors are incredible)
• Also good: Everything. This is the best hiking season.
• Skip: Nothing
• Watch out for: Crowds at Starved Rock on weekends (GET THERE EARLY)

November (Late Fall):

• Best: Any trail (crowds are gone)
• Also good: Waterfall Glen, Cook County preserves
• Skip: Nothing, but it's getting cold
• Watch out for: Early season ice, shorter daylight hours

December-February (Winter):

• Best: Waterfall Glen (accessible, less icy), Busse Woods
• Also good: Starved Rock if you have traction devices and good gear
• Skip: Devil's Lake (too icy/dangerous), trails after ice storms
• Watch out for: Ice, shorter days, hypothermia risk if you're unprepared

Final Thoughts

Chicago's hiking isn't going to compete with Colorado or the Pacific Northwest. But for a major city in the flattest part of the country, we've got surprisingly decent options within a couple hours' drive.

Start with something easy like Busse Woods or Waterfall Glen. Work your way up to Starved Rock. If you really want a challenge, make the trek to Devil's Lake.

And for the love of god, if you go to Starved Rock on a fall weekend, go early. I can't stress that enough. I've been stuck in the parking lot traffic and it's genuinely depressing watching the sunrise while you're still half a mile from the trailhead.

The best trail is the one you'll actually go to. Don't overthink it. Just pick one and go.

Before you head out, make sure you've got the basics covered. Good socks and a decent base layer will save you from a miserable day on the trail—trust me on this. If you're starting from scratch, our women's hiking collection and men's hiking collection have the essentials that'll work across all four seasons. For the full range of what we carry, you can browse our complete merino wool collection.

Now get outside. Your couch will still be there when you get back.

**About the Author:** Alex Chen is a Chicago-based outdoor enthusiast and freelance writer who has spent the past six years exploring Midwest hiking trails.

 *This article was contributed by guest writer Alex Chen. The personal voice, anecdotes, and opinions expressed are the author's own and reflect their individual hiking experiences.*