8 Great Hikes With Challenging Climbs Near Chicago

by Justyna Frank
Hikes with challenging climbs near chicago

OK, so maybe Chicago doesn’t offer many climbing opportunities right out of your front door. Illinois is the second flattest state in the union (trailing only Florida), therefore you may have to be willing to travel a bit if you want to climb anything other than the steps of the Sears Tower (I’m a lifelong Chicagoan — it’s always going to be “Sears Tower” for me).

But if you’re up for a day trip, I have great news for you. There are numerous scenic hikes with challenging climbs near Chicago! Within just a 1-3 hours’ drive you can access hiking trails with enough steep climbs to get you out of breath, distance to make the hike a worthy day’s adventure, and views guaranteed to restore your faith in the world.

In a hurry? Here’s a quick list:

Our Favorite Hikes with Challenging Climbs Near Chicago:

  1. Swallow Cliff Steps & Sag Valley Trails, SW suburban Chicago
  2. West Beach Trails at Indiana Dunes National Park
  3. Cowles Bog at Indiana Dunes National Park
  4. 3 Dune Challenge at Indiana Dunes State Park
  5. Grand Mere State Park, MI
  6. Mississippi Palisades State Park, IL
  7. Devil’s Lake State Parlk, WI
  8. Emma Carlin Trails at Kettle Morraine Southern Unit, WI
Rock scramble at Mississippi Palisades
Traversing the snow-covered dunes at Grand Mere
Steep barefoot climb at Cowles Bog

Swallow Cliff Steps & Sag Valley

Highlights: Fitness Steps and direct access to some of the most remote natural areas of Cook County.

The 100-foot-high bluff and the famous Swallow Cliff Woods stairs attract fitness visitors from beyond the Chicago region. Located at Swallow Cliff Woods North, and constructed in 1930 by the Civilian Conservation Corps, the 125 limestone stairs lead to the top of a former toboggan run. In 2016, the Forest Preserves added another set of stairs with an additional 168 steps, creating a full circuit.

The stairs are fun and rewarding to climb, but –even better– they serve as a gateway (and terrific warm-up) to the wonderful trails of the Sag Valley Trail System where hikers can experience woodlands, marshes and sedge meadows and other features of this uniquely Midwestern landscape.

For a rewarding day tour through Sag Valley that will provide equal amounts of woodland serenity and vigorous exercise, start at the stairs to get your blood pumping. From there, for a nice, long day hike, join the 8-mile Yellow Loop, a gravel and crushed stone multi-use trail.

Although not as dramatic as the stairs, the length of the trail and the rolling topography make it a stimulating hike. If you complete the entire loop, you’ll encounter some ridges and valleys as you head trough the Cap Sauers Holding Nature Preserve, and a steep hill around 40 Acre Woods.

More info: Sag Valley Trail System home page; Map of the Sag Valley Trail System.

About 25 miles, or 45 minutes from Downtown Chicago.

West Beach, Indiana Dunes National Park

Highlights: Steep stairway leading to overlook platform with sweeping Lake Michigan views.

For peace and solitude, we strongly recommend that you explore this trail system off-season, since in peak summer season it is one of the most popular beach destinations. You have been warned.

The trail system encompasses 3.5 miles of designated hiking trails, and includes a half-mile elevated stairway and boardwalk that will definitely get you out of breath, as well as reward you with breathtaking 360° views of dramatic, bare sand dunes. I can’t think of another area in Indiana Dunes that offers such open views of the dune architecture, unobstructed by trees. Nestled among the dunes are several beautiful and tranquil interdunal ponds surrounded by very unusual for this region jack pine evergreen forest. Visiting off-season and in the early morning, we’ve been rewarded with a sight of a pair of coyotes hunting along the ponds.

The trails system includes the Long Lake Loop which is not to be missed, although it doesn’t offer direct access to Lake Michigan. There’s plenty of climbing here, as the trail skirts a tall dune, and winds over a boardwalk and ridge overlooking Long Lake teeming with beaver activity. It’s also an excellent birdwatching site. Crossing the park access road, the trail continues over a series of rolling dunes through the woods before coming to the edge of steep slope used as a sledding hill in winter. For extra challenge, you can do this trail in reverse starting with the climb up the sledding hill.

More info: West Beach NPS home page; Map of West Beach Trails.

About 40 miles, or 1 hour from Downtown Chicago.

Cowles Bog at Indiana Dunes National Park

Highlights: Surprisingly steep climbs and variety of habitats make this a fascinating hike in all seasons.

This has been our favorite Chicago day hike for many years! Total trail length is about 5 miles, but the main loop is just over 3 miles over highly variable terrain.

Cowles Bog is a fantastic trail during any season of the year. We’ve hiked it in knee-deep snow, in the dead of summer, and in the rain. Spring and fall are especially lovely. Biting flies can be quite bothersome in the summer and early fall — prepare well!

This trail is home to some of the most challenging climbs near Chicago. No, it’s not the Rockies. Duneland climbs are short but steep, and covered in loose sand that definitely adds to the effort. One steep and heavily rooted section may require the use of four limbs.

The “bog” in the name is misleading. It’s actually a fen, and its rich flora provides gorgeous and changing scenery throughout the year. In addition, the trail will take you through woodland, duneland and a wild Lake Michigan beach, which is a great place for a mid-hike picnic, or a cooling swim during summer months.

The mile-long Greenbelt Trail that leads to the outlying parking area is flat and linear, but it traces the outer edges of the giant marsh, offering fascinating glimpses into ongoing restoration efforts, and provides excellent opportunities for birdwatching.

More info: Cowles Bog NPS home page; Map of Cowles Bog Trail.

About 50 miles or 1 hour from Downtown Chicago

3 Dune Challenge at Indiana Dunes State Park

Highlights: This one is all about the climbs.

The 3 Dune Challenge is a trail in Indiana Dunes State Park that connects the summits of three of the tallest dunes in the park: Mt. Jackson, Mt. Holden, and Mt. Tom. The trail is 1.5 miles with 552 feet of elevation gain, which may not look like much, but there’s a reason they call it a “challenge” (other than marketing, that is).

Like most of the duneland trails, the 3 Dune Challenge trail features sand. LOTS of sand. Deep sand! Climbing on sand is frustrating business: with every step up, you tend to slide back down, sometimes a little, sometimes a lot. Depending on your footwear, with each step you may also be picking up a shoeful of sand, making you feel like you’re wearing ankle weights. Are you still game?

Oh, did I mention these dunes are steep? If you thought 1.5 miles was not too bad, I’ve got news for you: at 176 feet, Mt. Jackson is the smallest of the dunes. The third dune, Mt. Tom, boasts a set of steps leading to the top. You might think that a bunch of stairs would be not be a welcome sight after climbing two dunes that are already making your thighs burn. But, take heart: steps are actually easier to climb, and you make much more measurable progress. Plus, the view from the top is spectacular.

The 3 Dune Challenge lives up to its name, but it is doable for most ages and ability levels as long as you pace yourself. The trip back to the starting point from the las summit will let your breathing return to normal, since it’s mostly downhill or flat.

More info: Indiana Dunes SP home page; 3 Dune Challenge page.

About 50 miles or 1 hour from Downtown Chicago

What to expect at Devil’s Lake SP
Top of the dune sunrise at West Beach

Grand Mere State Park, MI

Highlights: Wind swept blow-outs make for super-challenging climbs.

So at this point you may be noticing a pattern: to find hikes with challenging climbs near Chicago, head for the dunes!

Grand Mere SP in Michigan falls neatly into that pattern. This quieter, less crowded next-door neighbor to the popular Warren Dunes State park is home to towering dunes, interdunal lakes, and 180° views of Lake Michigan.

In winter, snow-covered dunes and deep blow-outs make for dramatic scenery, and offer plenty of opportunity for heart-pumping hikes, or Nordic skiing with sufficient snow cover.

There are about 4 miles of trails forming a loop through open dunes and the wooded areas of the park, but they are neither marked nor particularly well-maintained. A 2-mile hike around Baldtop, involves steep climbs through soft sand (or, in winter, lumpy snow), but will reward you with lung-fulls of fresh air, gorgeous scenery and excellent views.

Grand Mere is a prime example of dune succession from aquatic to terrestrial ecosystems. The interdunal lakes reveal the progression from open water turning into marsh, then woodland swamps and closed bog forests. The park sits along about a mile of Lake Michigan beach, which –when not covered with shelf ice and accessible– it a great place for mid-hike picnic.

More info: Grand Mere SP DNR home page. Map of Grand Mere SP.

About 90 miles or 1.75 hours from Downtown Chicago

Mississippi Palisades State Park, IL

Highlights: Challenging rock scrambles with grand views of the Mississippi.

If you’ve been dying for some climbs within a day-trip distance of Chicago, the trails in the Mississippi Palisades will give you what you’re looking for. The park trail system consist of 15 miles of trails.

The southern section is made up of tight footpaths and switchbacks that get perilously close to edges of bluffs and ravines, have some steep rock scrambles, and require your full concentration, particularly in icy conditions. Leaf litter can also be treacherously slippery, so although these trails are not very long, they can be quite demanding, and even hazardous under certain conditions. (Note: sections of the Sunset Trail have been fortified with a plastic grid, possibly in an effort to control erosion. This material is extremely slippery in near-freezing conditions, and I hope the park’s management reconsiders its use.)

The Northern section trails are wider and less strenuous, as they follow defunct road beds. They’re suitable for walking or running abreast, and you can combine them into a fairly long composite hike if you have time at your disposal, or mix’em up with the more rugged trails in the south portion for a hike that offers the best of all worlds.

The views of the Mississippi River from numerous area overlooks are astounding.

More info: Mississippi Palisades SP home page. Map of MPSP Trails.

About 155 miles or 3 hours from Downtown Chicago.

Devils Lake State Park, WI

Highlights: Scrambling over ledges and boulders to view spectacular rock formations.

OK, you’re done with the dunes, and you’re up for more rugged terrain. Wisconsin has more of that than you can shake a stick at, and southeast Wisconsin trails offer great hiking within a relatively short drive from Chicago.

Devil’s Lake Devil’s Lake SP is a10,000-acre park is for the adventurous at heart, featuring 500-foot quartzite bluffs, hiking, rock climbing, swimming, fishing, and even scuba diving. It’s pretty clear we’re not in Kans… –er, Illinois– anymore.

There are 14 total trails within the park featuring some of the most challenging climbs near Chicago that you’ll find.

The short but extremely rugged trails –including Balanced Rock, Potholes Trail and CCC Trail– are clustered near the southeastern edge of the lake, and are characterized by rocky ascents, narrow stone staircases and steep scrambles. Because of their proximity to one another, the somewhat less challenging (but spectacular) trails such as the Devil’s Doorway Loop, and more moderate, but longer trails that encircle the park, they can conveniently be strung into a longer hike with a good balance of difficulty, distance and stunning views.

More info: Devil’s Lake SP hiking trails page. Map of trails at Devil’s Lake.

About 190 miles or 3.5 hours from Downtown Chicago.

Emma Carlin Trails at Kettle Moraine State Forest, Southern Unit

Highlights: The long and rugged trails almost make you forget you’re in the Midwest.

The Kettle Moraine State Forest is a vast rugged, natural refuge in southeastern Wisconsin. Emma Carlin Trails are a little more remote and slightly less trafficked than the neighboring John Muir trails, but this trail system is an extremely popular mountain biking destination, so be prepared and alert when hiking there.

A long segment of the 1000-mile Ice Age Trail traverses the park, skirting along side several loops of the single-track mountain biking trails. Hiking on that section of the Ice Age would keep you away from mountain bikers entirely. However, the Ice Age Trail is generally linear, and you may need to retrace your steps, or get a ride, to return to your starting point.

The nice thing about the MTB trails is that they are loops, and you will conveniently end up at the starting point when you’re done hiking. There are provisions for trail sharing, and on the Emma Carlin trails, hikers travel clockwise, while cyclists ride counter-clockwise. On these trails it pays to choose less than perfect weather. Mountain bikers’ etiquette dictates they stay off trails in muddy conditions, so you may find the trails less crowded on damp days or when there has been a thaw.

Depending on your fitness level, time available and commitment to hiking on any given day, the tree loops at Emma Carlin offer a nice range of options of about 3, 5 or 7 miles, all of which include series challenging climbs and descents. The trails are heavily wooded and beautiful, with lots of rocks and roots that make for an interesting hike, and nice overlooks where you can break out a mid-hike lunch.

More info: Kettle Moraine Southern Unit hiking info. home page. Map of the Emma Carlin Trail System.

About 155 miles or 3 hours from Downtown Chicago.

Before you go

Please note that many of these trails are rugged, and the seasons can dramatically change the conditions of the trails. Check the trail websites for any updates, and, depending on weather, be prepared for insects, mud or ice (in freezing conditions, microspikes are a must!).

Some of the trails listed require and entrance fee. Check their websites for up-to-date fee information.

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