Backpacking trails in the Midwest, specifically near Chicago?

Its worth checking out the Manistee River Trail in Western Michigan.

Awesome, this looks like a great first trip. Thanks!

Great, Enjoy :-)

Not exactly a loop but my go to hike/backpack when I lived in Madison was South Kettle Moraine State Park near Whitewater WI. Depending on where you are in Chicago about a two hour drive. The North Kettle Moraine is nicer but a little further travel time. Both have many miles of some really great trail, the only downside not a loop.

Have you looked into the Ice Age Trails of WI?
GO HERE

Also check out Chequamegon National Forest:
GO HERE

Chequamegon Lower North Part
Rock Lake National Recreational Trail

Chequamegon Upper North Part
Teuton and Vallkyrie Trails

Nicolet North Part
Lauterman National Recreational Trail

Flambeau River State Forest
Flambeau Hills Trails

Thanks everyone for the suggestions, these are all great!

You might look at Yellow River State Forest in NE Iowa, about 15-20 miles NW of Prairie du Chien WI. It would probably be around 4-5 hours, depending where you are in Chicago. It would be a good place for a first hike for a few reasons.

First, you are never more than a mile or two from a FS road. There are 25 miles of trail, but they criss-cross the SF, as do several narrow gravel roads. I'm not sure how you could possibly get lost in the place, but if you did, you would only have to walk an hour or two in any direction to hit a road or park boundary (read: cornfield :-)

Second, there are four established campsites on these trails with fire rings and log benches which make for great campfire time. Two of the sites have multiple campfire rings, one has a pond, one has a sweet flat area under some pine trees that is an excellent tent pad, one has a group site complete with an adirondack shelter that will sleep 6-8. Often the convicts from prison up the road have stocked firewood at some of these sites. The two that only have one campfire ring are fairly secluded and you can believe at night that you are in the wilderness.

Third, the trails are fairly easy, but have some varied terrain. I think there is only around 300 feet difference between the high and low spot in the park (there's only 1200 feet difference between the high and low spot in Iowa!), but you traverse that up and down quite a few times. You can make the route fairly challenging if you want to.

A few things to think about though. It is not recommended to drink the surface water in Iowa at any time of the year (though I know some people do early in the year before the farm chemicals get applied), so you will need to cache water. This is easy to do since the trail crosses the FS roads quite a few times and you can just drive up the road when you first get there and cache water just off the trail in a few spots. Also, some of the trails are multi-use, so watch out for them horse apples! A couple of the sites are within walking distance of roads as well, so sometimes you see a hardy soul that has humped in their car camping gear, but I've never had a problem with anyone.

I am very familiar with the place since it is 3.5 hours, as opposed to the 8-9 hours to get to any real trials from central Iowa. It is our go-to spot for a quick weekend. It also has some of the best car camping campgrounds around. As I said, I know the place extremely well, so let me know if you would like more information.

Happy Trails!

I've been backpacking for more than 30 years in and around the Chicago area and I'm not sure there's a trail I haven't done if you can reach it on a weekend trip from Chicago.

+1 on Manistee River Trail loop. Super easy and very nice scenery. Probably my favorite easy weekend getaway.

Jordan River, also in north central MI, but this is probably about 6 hrs away. Very nice loop, but you can only camp at the backpackers campground at the halfway point. But honestly, it's a very nice campground (and I generally detest campgrounds).

Charles Deam in the Hoosier National Forest, near Bloomington, IN. Great campsites off the main trails…and easy bushwhacking. There's a famous cave that isn't marked on any map but very fun to find.

Red River Gorge in northern KY. About an 8 hour drive but WELL worth it. It doesn't get much better than here for scenery in the Midwest.

The Porkies. Obviously. But also an 8 hr drive…so make it a 4-day weekend, but about the only true wilderness you can get within a day's drive from the city.

Tecumseh Trail in the Morgan-Monroe State Forest. Just south of Indianapolis, it makes a great point-to-point hike to do a nice 18-mile stretch over the weekend. Also easy hiking. But can get really, really miserably hot n humid in the summer

The granddaddy in southern Indiana is the Knobstone Trail…its a beauty!! You have to do that one in the spring because the water dries up over the summer.

I hope that helps!!!!