Perfect Fall Road Trips for When You Need to Escape Chicago

There are plenty of day trips near the Windy City when you need a quick reset.

No need to wait until summer 2023 to hit the open road. The road is always open. Before winter sets in and the obligatory family holiday gatherings are etched into the calendar, why not plan an impromptu mini fall road trip right near Chicago? Just remember to bring your fall essentials: sweater, scarf, boots, and maybe that book that you were “going to read this year.” Fall happens to be an ideal time to cruise the open road because the traffic is chill, the crowds are thin, the pace is slow, and the colors are stunning. Relax inside a cozy Airbnb or tiny house nestled in the woods, take a crisp hike to admire the changing leaves, or pick a bushel of apples from a local orchard to bring home. No matter what the motivation, here are 15 amazing destinations you can road trip to this fall.

Discover Holland
Discover Holland

Distance from Chicago: 152 miles, 2.5-hour drive
If you hook around the belly of Lake Michigan you’ll find Holland, Michigan, a charming town that sits right off of beautiful Lake Macatawa. Take a chilly stroll along the stunning beaches; meander through historic downtown where you’ll find numerous specialty shops, art galleries, and restaurants; post up at one of the many breweries like Big Lake Brewing and New Holland Brewing; or visit their weekly farmers market (open to the end of October). Before you head back to your stay, finish the day with a spectacular sunset view at lakeside Tunnel Park or Window on the Waterfront, a 30 acre park along the shore. It’s the kind of place that will remind you that you do in fact like pumpkins and maybe even pumpkin spice too.
Stay: Find a great Airbnb in Holland Michigan

Getaway Barber Creek
Photo courtesy of Getaway Barber Creek

Distance from Chicago: 133 miles, 2.5-hour drive
Ever wanted to say, “Screw it all,” get rid of all your earthly belongings, and hole up in a hygge-ified tiny house in the middle of nowhere? Live out all your reclusive fantasies without actually tossing your stuff by booking a weekend in Grand Junction, a pastoral sliver of western Michigan about 15 minutes outside the lakefront hamlet of South Haven. That’s where you’ll find Getaway Barber Creek, a 79-acre dog-friendly glamp-ground outfitted with a handful of secluded cabins complete with parking spots, picnic tables, Adirondack chairs, and fire pits for all your marshmallow-melting needs. Each matte black hideaway is as practically appointed as it is aesthetically pleasing, stocked with a plush, super comfy bed, gorgeous floor-to-ceiling window, compact table, kitchenette with running water, and full bathroom with, yes, a real-deal shower.
Outside the confines of your oasis lies plenty of outdoorsy and less-outdoorsy activities, from hiking the converted railroad Kal-Haven Trail or sand-strewn Van Buren Park Dunes Trail to checking out the historic South Haven South Pierhead Light or stuffing yourself silly at area farm-to-table eateries and top notch breweries. Whatever you choose, embrace your new lifestyle—however temporary—by stashing your phone in the lockbox provided, cozying up with a good bottle of whiskey (preferably something camp-ready like Stillhouse), and reveling in the simplicity of it all.
Stay: Find a great Airbnb near Illinois Beach State Park

Michigan City Lighthouse
Michigan City Lighthouse | Jaclyn Novak/Shutterstock

Distance from Chicago: 60 miles southeast, 1 hour drive
Only have time for a quick breather from the city? No problem. Michigan City Indiana is a charming town along the southern shoreline of Lake Michigan and neighbors the venerable and incredibly diverse landscape that is the Indiana Dunes. The two parks, Indiana Dunes State Park and Indiana Dunes National Park sport miles of sandswept mounds along the lake’s shores, and have many trails wandering through dense woodland and serene prairie that will no doubt excite with their autumnal splendor. The town itself is packed with things to do from shopping at the massive outlet mall, hitting up one of the town’s breweries, to eating locally at one of the town’s many yummy restaurants.
Stay: Find a great Airbnb in Michigan City, Indiana

Madison, Wisconsin
Madison, Wisconsin | SamuelJLi/Shutterstock

Distance from Chicago: 147 miles northwest, 2.5 hour drive
Madison, Wisconsin is special because it has all the city perks, like quality restaurants and historic venues, while also being surrounded by a plethora of nature-filled fall activities. Hike until your heart's content amongst the autumnal trails, and then order an old fashion from any of the vibing local bars (Robin RoomThe Malt House, Working Draft Beer Company, Cask & Ale). There are plenty of drivable country activities, but the University of Wisconsin Arboretum is nestled closely within the city proper and has a variety of diverse paved and dirt trails covering its eclectic landscape. You don’t have to be an architecture nerd to appreciate Frank Lloyd Wright's famous estate, Taliesin, and on your way back, you can visit Blue Mounds State Park, to enjoy some stellar fall views from the tallest point of this region of Wisconsin.
Stay: Find a great Airbnb in Madison, Wisconsin

Illinois Department of Natural Resources
Illinois Department of Natural Resources

Distance from Chicago: 46 miles north, 1.5 hour drive
Zion Illinois is a stunning lakeside town straddling Wisocnin’s border and will give you a serene intermission without the time commitment. The town’s chief attraction is the stunning 4,000-acre Illinois Beach State Park where you can recharge by meandering along its vast shoreline, biking their north to south trails, or hiking beneath the changing savannah oak trees. The town itself has several humble local hotel accommodations, but this state park is best to experience as a camper—so don’t stash your tent in storage just yet, pick up a bundle of firewood, and get cozy beneath the fall night sky. After traversing the state park, there are also numerous nearby forest preserves and river trails to experience like Van Patten WoodDes Plaines River Trail, and the Pine Dunes Forest Preserve.
Stay: Find a great Airbnb near Illinois Beach State Park

Starved Rock State Park
Starved Rock State Park | Jason Patrick Ross/Shutterstock

Distance from Chicago: 94 miles southwest, 2-hour drive
The historic town of Ottawa, located at the intersection of the Fox and Illinois Rivers, is best known as the entryway to Starved Rock State Park, where tall bluffs and canyon waterfalls provide one of the finest outdoor experiences near Chicago. While it is the most popular state park in Illinois, Starved Rock still manages to create one of the finest hiking and camping destinations around with 18 glacier-carved canyons and more than 13 miles of trails. Don’t miss the equally cool bluff-side expanses of nearby Matthiessen or Buffalo Rock State Park. And if you can swing a room for the night at the National Register of Historic Places-listed Starved Rock Lodge, by all means, you should. You can even hop aboard a river cruise which runs through October or tread alongside an expert on a guided hike tour which runs through November. Wherever you stay though, there is plenty to do in and near Ottawa including plenty of pumpkin and apple picking.
StayFind a great Airbnb near Starved Rock State Park

Historical Galena Town Main Street
Historical Galena Town Main Street | Nejdet Duzen/Shutterstock

Distance from Chicago: 164 miles northwest, 3-hour drive
As one of the best small towns in America, Galena has you covered if you're into strolling cobblestone streets amidst historic mansions and scenic rolling hills. With the entire Galena Historic District (home of more than 1,000 buildings constructed before 1900) listed on the National Register of Historic Places, you won’t have to wander far to realize why Ulysses S. Grant chose to make his home here. If you're feeling more outdoorsy, Galena is a great place to enjoy outdoor activities boasting a number of cool bluff hikes overlooking the Mighty Mississippi. Stay off General Grant's beaten path at the snug LeFevre Inn which is nestled on 100 acres of land just outside of town. If you’re interested in a fall hike, some of your best bets include the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park.
StayFind a great Airbnb near Galena

Oval Beach
Oval Beach | FotoKina/Shutterstock

Distance from Chicago: 139 miles northeast, 2.5-hour drive
Saugatuck is famous for the pristine Oval Beach (cited by the Tribune as the Midwest's best beach). But Saugatuck’s arts scene is what really sets it apart. Known as “the art coast of Michigan,” Saugatuck and the nearby towns of Douglas and Fennville are home to dozens of art galleries and unique shops tailor made for a laid-back meander through the gallery-lined downtown district. The open-minded community is also extremely accommodating to all lifestyles, with more than 140 LGBTQ-owned and gay-friendly businesses making it one of the most queer-friendly small resort towns in America. Plus, you’ll find plenty of great restaurants, breweries, wineries and distilleries all around town.
StayFind a great Airbnb near Saugatuck

Road America
Road America

Distance from Chicago: 150 miles north, 2.5-hour drive
This charming little hideaway about 30 minutes west of Sheboygan is often overlooked but shouldn’t be. The laid-back, pretense-free 292-acre lake boasts some of the clearest waters in Wisconsin, in addition to some A-plus fishing. The AAA Four Diamond Osthoff Resort is a popular choice, but the area also offers a wealth of nature to get lost in thanks to its location near the gorgeous 30,000-acre Kettle Moraine State Forest. Hike sections of Wisconsin’s 1,200-mile Ice Age National Scenic Trail, explore the area’s rolling hills via bike on the 17-mile Old Plank Road Trail, and be sure to spend some on your keister enjoying the view from the Osthoff’s private beach or the public Fireman’s Park. Fall classics include brew tastings, hiking, biking, and no one ever hated on a crisp drive through Kettle Moraine.
StayFind a great Airbnb near Elkhart Lake

Anaway Place
Anaway Place

Distance from Chicago: 208 miles northwest, 3.5-hour drive
With seven spectacular cabins including the stunning glass-walled Meadow House, Candlewood Cabins in rural Richland County located about an hour west of Madison is a nature escape tailored for your fall getaway. Each private cabin looks out into the rolling hills and scenic fields that surround the grounds, with some walking trails like The Ridge Road starting right at the foot of your cabin. Spot wildlife including birds and deer, or explore the 15-mile Pine River Recreation Trail by bike over an abandoned railroad line dotted with bridges. The area also boasts five state parks within an hour’s drive, including the 100-mile Lower Wisconsin River Scenic Byway.
StayFind a great Airbnb in Richland County

Wild Tomato Wood-Fired Pizza and Grille Fish Creek
Ridges Sanctuary | Wild Tomato Wood-Fired Pizza and Grille Fish Creek

Distance from Chicago: 276 miles north, 4.5-hour drive
Known as the “Cape Cod of the Midwest,” Door County is a picture-perfect assemblage of more than a dozen great little towns situated on a beautiful 75-mile peninsula surrounded by the shimmering waters of Lake Michigan and Green Bay. With five state parks and 300 miles of shoreline views, there's a lot to like (and do) here. Explore some of the area’s nature-filled destinations such as the 7,000 acres of pristine open space preserved by the Door County Land Trust or the peaceful lighthouse-dotted Ridges Sanctuary as you listen to nothing but the sound of the rustling leaves dancing on the fall breeze. Be sure to check out other hidden natural gems such as Baileys Harbor Ridges County Park or the breathtaking Hotz Memorial Town Park. The area is also dense with fall activities from trolley tours and roadside farm stands to country stores and fall farmer’s markets.
StayFind a great Airbnb in Door County

The Parklands of Floyds Fork
The Parklands of Floyds Fork

Distance from Chicago: 300 miles, 5 hour drive
Louisville might be known for, you know, Kentucky fried chicken, and the Kentucky Derby, but there are actually so many more reasons to put this town on your bucket list. Walk through the bourbon district and sip your way around the many distilleries, from family-run favorite Peerless to well-known giant Evan Williams, or opt for the lighter stuff and get your fill of the bottomless breweries around town, like Chimera Brewing Company, Falls City Beer, Akasha Brewing Company, and more. Besides drinking, you can meander through Louisville’s vibrant historic Frankfort Avenue, a 2.5-mile stretch of boutiques, galleries, restaurants, and bars, get cultured and visit one of their outstanding museums like Roots 101 African American Museum, Louisville Slugger Museum & Factory, or seek some autumnal serenity at nearby parks The Parkland of Floyd Fork and Cherokee Park.
Stay: Find a great Airbnb near Louisville

Point of View Lake Resort and Glamping Campground
Point of View Lake Resort and Glamping Campground

Distance from Chicago: 311 miles northwest, 5.5-hour drive
If you’re looking for the great Wisconsin Northwoods experience, it’s time to point your GPS towards under-the-radar Vilas County. The charming tourist communities of Eagle River and Minocqua are essential area attractions, but for a better and more off-the-beaten path experience, check out the unrelentingly awesome Coadys’ Point of View Resort in the town of Phelps near Wisconsin’s border with Michigan’s Upper Peninsula. Tucked away on the peaceful shores of North Twin Lake within the massive 661,000-acre Nicolet National Forest, the resort offers everything from cozy cabins to luxury glampsites.
StayFind a great Airbnb in Vilas County

Shawnee Hills Wine Trail
Shawnee Hills Wine Trail

Distance from Chicago: 351 miles southwest, 5.5-hour drive
No one is going to mistake Illinois for a natural wonderland, but the Land of Lincoln has one ace up its sleeve: Shawnee National Forest, a brilliant expanse of approximately 280,000 acres that covers a large portion of the southern tip of Illinois. In other words, it’s the perfect spot to take a much-deserved break from the endless crush of bad news for a few days. Bask in the solitude of the national forest’s epic Garden of the Gods Wilderness (one of seven wilderness areas in the park) before making a peaceful meander through the Shawnee Hills Wine Trail: a 35-mile scenic drive featuring 11 award-winning wineries dotted throughout rural countryside towns like Cobden, Alto Pass, and Pomona.
StayFind a great Airbnb near Shawnee National Forest

U.S. Forest Service
Pictured Rocks National Lakeshore | U.S. Forest Service

Distance from Chicago: 380 miles northeast, 6 hour drive
The upper peninsula of Michigan is a truly spectacular piece of the Midwest that is often overlooked by Chicagoans, as it does require more road time. But don’t let the distance discourage you. Pictured Rocks National Lakeshore includes 42 miles of glorious views along the southern dip of Lake Superior, and really packs a punch with endless forests (i.e., a leaf peepers paradise), and multi-colored rocky ridges with some as high as 200 feet. You won’t want to miss the Miners Castle and Chapel Rock, both impressive craggy cliffs which stand apart from the rest because of their peculiar shapes and size. Whether you want to hike through the forest or bike some backroads trails, this natural paradise will keep you occupied for a long fall weekend for sure. Munising Township is stocked with restaurants, bars, and humble accommodations if fall camping doesn't sound appealing. Also, Hiawatha National Forest is 15 miles away so you get two for the price of one.
Stay: Find a great Airbnb near Pictured Rock National Lakeshore

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Elanor Bock is a Chicago born, New York-based professional dancer, writer, and renaissance woman, excelling at philosophy, mathematics, outdoor adventuring, and balancing six martinis on a tray in a crowded bar.
Jay Gentile writes about food & drink, travel, events, entertainment, and culture for Thrillist.