• Lauren H

Training for Hikes Near Chicago

Updated: Jan 9


View From the Soldier Field Sledding Hill
View From the Soldier Field Sledding Hill

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Training Strategy

Hills to Train on in Chicago

Hikes with Elevation Gain in Driving Distance of Chicago


Training Strategy

I recently won the lottery for a two-day hike on Mt. Whitney, a 22-mile hike with over 6,000 feet in elevation gain to the tallest peak in the lower-48. I won the permit on May 1st and the hike started July 7th. I only had two months to train and I live in flat Chicago!


I know some Midwest hikers train on a stairmaster in the gym with a pack on, but that sounded boring to me. Rather than using a stairmaster, I instead decided to focus on weekly hill repeats with a pack on plus a couple added on trips to actual hikes with elevation gain, within driving distance of Chicago.


Starting 8 weeks out from my hike, once a week I went to a local hill (options are outlined below. I wore a 30lb pack and hiked up and down for an hour to 90 minutes. I filled my pack with water and heavy foods and then used a luggage scale to weigh it. I tried to train with more weight than what I would end up backpacking with. The last three weeks before the hike, I increased these hill sets to 2x per week. The first couple of times I wore the heavy pack, I had hip pain as well as sore legs and hips afterwards. This training helped to eliminate that pain and soreness, and ultimately strengthened the muscles I needed to carry the pack. I wanted my muscles to be accustomed to the weight of the pack and to the uphill movements and this strategy worked!


In addition to the hill and pack training I increased the amount of HIIT workouts I attended at the gym to help improve my cardio. If I planned on one day of hills a week, then I aimed for 5 days at the gym. If you are a runner, adding in more running to improve your cardio is another option.


I also added weekly yoga to help with flexibility and to decrease soreness/prevent injuries.


The above strategy works well for training for any backpacking trip or hiking trip.


Hills to Train on in Chicago


Soldier Field Sledding Hill- 30 feet tall

If you follow the LakeShore path south of Soldier Field you this hill is visible on your right, before you hit McCormick Place. There are often runners going up and down the hill. To accomplish the steepest workout possible I went up and down the main section of the hill (oftentimes runners loop around the less steep backside).


Running Up The Soldier Field Sledding Hill
Running Up The Soldier Field Sledding Hill

Cricket Hill- 45 feet tall

This hill is located next to Montrose Beach and is directly off of the LakeShore running and biking path. There are regularly other runners repeating hill routes here and all four sides of the hill are accessible to use.


Cricket Hill Chicago
Cricket Hill

Mt. Trashmore- 65 Feet Tall

This hill is a former landfill that is now part of Robert E. James Park in Evanston. I liked this spot for a few reasons. There are actual dirt trails carved out amongst trees, so it feels closer to hiking. There are multiple (~4) trails to go up and down so there’s more variety when you train. It’s slightly less boring than going up and down the same path for an hour. The trail on the backside of the hill was the steepest.


View from the Top of Mt. Trashmore Evanston
View from the Top of Mt. Trashmore

One of the Dirt "Trails" on Mt. Trashmore Evanston
One of the Dirt Trails on Mt. Trashmore

Swallow Cliff Stairs- 100 feet tall

Depending on where in Chicago you live, it’s a 20-40 minute drive to this bluff in Palos Heights. I recommend going early on Saturday or Sunday morning to beat traffic. This hill has carved out stairs with an up section on the left and a down section on the right. It is full of runners, other people working out and even a few fellow hikers with packs. I recommend targeting one or two training sessions here to give your muscles experience on both hills and stairs.



Swallow Cliff Stairs
Swallow Cliff Stairs

Hikes with Elevation Gain in Driving Distance of Chicago


Indiana Dunes National Park, Indiana- 46 minutes from Chicago

Although the trails here still have relatively limited elevation gain, The 3-Dunes Challenge has 552 feet of elevation gain on sand. Going up and down the sand trail is a serious workout and rewards hikers with views of Lake Michigan at the top.



At the Top of the 3-Dune Challenge Indiana Dunes National Park
At the Top of the 3-Dune Challenge


Mississippi Palisades State Park, Illinois- 2 hours 45 minutes from Chicago

This park has hiking trails with elevation because it is located on bluffs of the Mississippi River. The trails in the park also lead to views of the river. The Sentinel, Sunset and Pine trail is a 4.5 mile loop with 1,089 in elevation gain.


Devil’s Lake State Park, Wisconsin- 3 hours from Chicago

The quartzite cliffs in this park were formed by a glacier a billion years ago. The trails in the park connect to a larger Ice Age Scenic Trail that goes throughout much of Wisconsin. The Devil’s Lake Trail via the West Bluff is a 4.7 mile trail with 997 feet in elevation gain. It wraps around Devil’s Lake with multiple Lake viewpoints.



On the Devil's Lake Trail
On the Devil's Lake Trail


Pikes Peak State Park, Iowa- 4 hours 20 minutes from Chicago

The Chinquapin Ridge Trail in this park is a 6.2 mile loop with 626 feet in elevation gain. It takes hikers to the tallest bluff on the Mississippi River.


At Pt. Ann in Pikes Peak State Park Iowa
At Pt. Ann in Pikes Peak State Park

Wyalusing State Park, Wisconsin-4 hours from Chicago

Pikes Peak State Park and Wyalusing are a short drive apart, so it’s easy to combine them for a weekend trip. The Sentinel Ridge Trail in Wyalusing State park is a 3.1 mile trail with 841 feet of elevation gain.


Sentinel Ridge Trail in Wyalusing State park
On the Sentinel Ridge Trail in Wyalusing State Park


Additional Reading: Camping Trips Near Chicago, A Camping Weekend on The Mississippi River, Everything You Need to Know for a 2-day Mt. Whitney Hike,What to Pack for a 2-Day Mt. Whitney Hike, Food Planning for a 2-day Mt. Whitney Trip,

Trip Dates: July 2021

Article Updated: July 2021

*Some links in this article are affiliate links that I receive a small commission for at no cost to you.