11 Perfect Fall Road Trips for When You Need to Escape Chicago

Coastal Michigan escapes, college town charmers, fairytale forests, and more.

Lover’s Leap Arch at Pictured Rocks National Lakeshore
Lover’s Leap Arch at Pictured Rocks National Lakeshore | Dean Pennala/Shutterstock
Lover’s Leap Arch at Pictured Rocks National Lakeshore | Dean Pennala/Shutterstock

The sweetness of fall has set in, and with it, the urge to escape the hustle and bustle of our busy work, home, and work-from-home routines. And while the local farmers market may provide a momentary seasonal fix, there’s nothing like loading up the car and setting off toward a brand new destination.

Luckily, a bounty of breathtaking naturescapes and charming mid-sized cities all sit a stone’s throw away from the Windy City, each with enough stunning views and unique activities for a full weekend—or even an entire week—of autumnal mini-vacay bliss. Turns out it is, in fact, possible to both unplug and recharge simultaneously, so pack the essentials, (i.e. phone, wallet, keys, mask, hand sanitizer) and embark on any one of these 11 hand-picked orange-hued respites from big city living.

Illinois Beach State Park
Illinois Beach State Park | Jacob Boomsma/Shutterstock

Illinois Beach State Park, Illinois

Distance From Chicago: 47.5 miles north, 75-minute drive
Only have time for a quick breather? Drive due north to this natural wonderland perched near the Wisconsin border, a lakefront refuge able to provide a serene intermission without the time commitment farther-flung destinations require. Illinois Beach State Park, located in the town of Zion, is where you can soak up the relaxing vibes while meandering along the vast shoreline, casting a reel into the lake’s crashing waves, biking the mixed-surface trails, or hiking beneath the soaring oak savannas. Armed with 4,160 acres of diverse terrain, the park is rife with opportunities to catch sight of colorful birds passing through during fall migration. Once you’ve had your fill, check out numerous nearby forest preserves and river trails including Van Patten Woods, Des Plaines River Trail, and the Pine Dunes Forest Preserve.

anatoliy_gleb/Shutterstock

As for Zion, you’ll find all the everyday staples you’ll need, including grocery stores, a seasonal public pool complete with an innertube slide, and quick-serve restaurants, plus some fascinating local lore and unique architecture stashed inside the Zion Historical Society (John A. Dowie, the leader of a turn-of-the-century fundamentalist Christian, er, “group,” founded the town expressly for his devoted congregation). And while it might be tempting to book a room at one of the chain hotels or motels in town, camping is by far the best way to experience this lovely State Park, with rustic and modern tent and RV sites open through New Year’s Day. So layer up, grab an extra cord of firewood, and get cozy under the crisp fall sky.

Devil's Lake State Park
Devil's Lake State Park | MarynaG/Shutterstock

Wisconsin Dells, Wisconsin

Distance From Chicago: 193 miles northwest, 3-hour drive
Wisconsin Dells is known not only for its killer collection of adult-friendly water parks, (what up, summer 2022?), but also for the Dells themselves: A magnificent gorge carved out by ancient glaciers, boasting powerful views of the sandstone cliffs lining the Wisconsin River. Dells of the Wisconsin River State Natural Area encompases five miles of beautiful hiking trails following the curving river, and if you’d rather marvel at the vibrant foliage from a comfortable seat, boat tours are available to guide you though the upper and lower Dells. The cruise also provides the best vantage point for taking in the enormous and unusual rock formations unique to the area. And if that’s not enough, nearby Devil’s Lake State Park in Baraboo offers similarly appealing vistas and additional outdoor revelvery.

Fawn Creek Winery
Fawn Creek Winery

Apart from a literal endless amount of theme parks, water parks, and natural splendors, the town itself is rife with charming features perfect for a fall getaway. Rest your head at quaint bed and breakfasts like Oak Hill and Cedar Lodge, indulge your inner gourmand at countless restaurants, (Brat House Grill, stationed in a colorful and gorgeously preserved Victorian home, is an absolute must), breweries and wineries like Fawn Creek and the beloved Moosejaw Pizza & Dells Brewing Co., and plenty of chances to get up close and personal with furry friends by way of Timbavati Wildlife Park and Wisconsin Deer Park. Suffice it to say, you won’t be getting bored anytime soon.

Pictured Rocks National Lakeshore
Pictured Rocks National Lakeshore | Oleksandr Koretskyi/Shutterstock

Pictured Rocks National Lakeshore, Michigan

Distance From Chicago: 380 miles northeast, 6-hour drive
Michigan’s Upper Peninsula is a truly spectacular piece of the Midwest, one that’s all too often overlooked by Chicagoans as it lies just outside the traditional five-hour road trip radius. But don’t let the distance discourage you—Pictured Rocks National Lakeshore is well worth the extra mileage, promising 42 miles of glorious panoramas along the southern dip of Lake Superior dotted with gushing waterfalls, pristine lakes, endless rugged forests, and rocky technicolor ridges stretching as high as 200 feet above the shore. Don’t miss Miners Castle and Chapel Rock, two craggy cliffs that stand apart from the rest due to their peculiar shapes and impressive sizes. Whether you’re in the mood to trek through the trees, kayak along the glistening shoreline, hop aboard a boat cruise (most open daily through mid-October), or shred some backroads trails on your bike, this natural paradise offers more than enough to occupy a full weekend of fall hijinks.

 

Shipwreck Tours - Glass Bottom Boat - Munising, Michigan
Shipwreck Tours - Glass Bottom Boat - Munising, Michigan

Fun fact: Historians widely consider this geographical area to be a burial ground for sunken and crashed ships dating back to as early as 1860. During the warmer months, curious seafarers can book a seat on a glass-bottom shipwreck tour to peer at the drowned relics from above (now through October 14). And in terms of creature comforts, Munising is stocked with all kinds of restaurants and bars plus inviting hotels, motels, cabins, and resorts if a chilly off-season camping trip doesn't sound appealing. Did we mention that Hiawatha National Forest and all its forested glory sits a mere 15 miles away? That’s two for the price of one.

Indiana Dunes State Park
Indiana Dunes State Park | Sarah Quintans/Shutterstock

Michigan City, Indiana

Distance From Chicago: 60 miles southeast, 1-hour drive
Michigan City is an idyllic town perched along the southern shoreline of Lake Michigan, engulfed by the venerable and incredibly diverse landscape of the Indiana Dunes. Indiana Dunes State Park and Indiana Dunes National Park combine for miles of sandswept mounds traversed a bounty of trails wandering through dense woodland, seren prairie, and swampy wetlands showcasing golden fall hues. Those interested in sleeping under the stars can do so year-round within the State Park or at several nearby all-weather camp and RV grounds (though you may want to cop a headed home on wheels via RVshare as the temperatures drop), while the National Park’s dreamy Dunewood Campground shuts down on November 1. Otherwise, book a stay at a cozy area outpost like The Brewery Lodge, an unforgettable rustic-chic boutique hotel set over 40 acres, or the retro-cool 4411 Inn & Suites, a renovated roadside offering private back patios and communal fire pits.

Journeyman Distillery
Journeyman Distillery

Prefer to balance your outdoor pursuits with a dose of small town charm? Michigan City is overflowing with things to do, from shopping at the massive outlet mall to picking a peck at apple orchards, vegetable farms, and pumpkin patches. A Michiana booze crawl is always in store, with standout producers Burn ‘Em Brewing, Shoreline Brewery, Zorn Brew Works, Shady Creek Winery, and nearby Journeyman Distillery among a plethora of others leading the charge. And when hunger inevitably strikes, get your local fill at polished restaurants like The Brewery Lodge’s onsite Supper Club, Fish Camp, and Fiddlehead alongside laid-back favorites like Bridges Waterside Grill, Hammers, and Barker Pub.

Downtown Madison, Wisconsin
Downtown Madison, Wisconsin | Suzanne Tucker/Shutterstock

Madison, Wisconsin

Distance From Chicago: 147 miles northwest, 2.5-hour drive
Maybe you’re not exactly keen on heading to another city for your autumnal escape, but this college town gem might just sway you by merging citified perks like a quality dining scene and world-class cultural venues with an onslaught of nature activities like hiking, biking, fishing, and boating. Gear up to tackle one or more of Madison’s many urban and exurban amber leaf-strewn trails before cleaning up, masking up, and rewarding yourself with a Wisconsin-style Brandy Old Fashioned from a buzzy local watering hole. Top options include Robin Room, The Malt House, Working Draft Beer Company, and Cask & Ale—but that’s just scratching the surface. Head-turning restaurants are another specialty, so make a point to stroll the always-vibing State Street promenade to scope out satisfying casual and global eateries or snag a table at one of the farm-to-table gems scattered around town. Save room for beer from craft champions like Ale Asylum, Lone Girl, Young Blood, and Funk Factory Geuzeria, and when it comes time to crash, AC Hotel Madison Downtown, The Livingston Inn, The Edgewater, and the upbeat Graduate Madison (two words: rooftop bar) have your back… literally.

UW-Madison Arboretum
UW-Madison Arboretum

Plenty of pastoral and lakeside draws await once you’ve had a good night’s sleep. The University of Wisconsin Arboretum is nestled within the city proper, with a variety of paved and dirt trails criss-crossing its eclectic expanse. And you don’t have to be an architecture nerd to have your mind blown at Frank Lloyd Wright's famous Taliesin estate, a majestic and artfully preserved UNESCO Heritage Site located just south of nearby Spring Green, Wisconsin. On your way back to the Chi, stop off at Blue Mounds State Park for some awe-inspiring leaf peeping courtesy of the region’s highest lookout point.

Lake Geneva Balloon Company
Lake Geneva Balloon Company | Photo courtesy of VISIT LAKE GENEVA

Lake Geneva, Wisconsin

Distance from Chicago: 80 miles northwest, 1.5-hour drive
There’s a reason why Lake Geneva has been Chicago’s number one vacation destination for generations. It’s got everything you could possibly need in a weekend oasis… all just 90 minutes from the city. As one of America’s best lake towns, it boasts an array of activities from booze cruises and hot air balloon rides to a stomach-satisfying food and drink scene. And the nice thing about Geneva in the fall is that it’s much tamer than the extremely busy summer months. However, if you find the postcard-perfect downtown still abuzz with tourists, get some fresh air by walking the entire length of the lakeshore along the town’s open-to-the-public Lake Shore Path before taking refuge in under-the-radar Lake Como, home to the epic Mars Resort and its newly expanded patio. The lesser-visited towns of Williams Bay, Fontana, and nearby Lake Delavan are also more than worthy of exploration any time of year.

Starved Rock
Starved Rock | PHOTO COURTESY OF VISIT ILLINOIS

Starved Rock State Park, Illinois

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 in proximity to the Windy City. While it stands as the most popular state park in Illinois, Starved Rock still manages to keep the crowds at bay just enough to secure its status as one of the finest hiking and camping destinations around,with 18 glacier-carved canyons and more than 13 miles of trails.

Avoid hoards of leaf peepers this fall with a trip to the equally cool bluff-side expanses of nearby Matthiessen State Park and Buffalo Rock State Park, both fantastic preserves that remain wonderfully underrated when it comes to foot traffic. And if you can swing a room for the night at the National Register of Historic Places-listed Starved Rock Lodge, by all means, do. You can even up the ante by hopping aboard their Fall Color Trolley Tour or Autumn on the River Cruise. Restaurant options span two town centers: Utica and Ottawa. Each is stocked with enticing wine bars and tasting rooms like August Hill Winery, friendly pubs in the form of Lodi Tap and stellar breweries like Tangled Roots Brewery Company.

Shawnee National Forest
Shawnee National Forest | Eddie J. Rodriquez/Shutterstock

Shawnee National Forest, Illinois

Distance from Chicago: 351 miles southwest, 5.5-hour drive
No one is going to mistake Illinois for Big Sky Country, but the Land of Lincoln has one ace up its sleeve: Shawnee National Forest, a brilliant stretch of approximately 280,000 acres covering 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. Tent, RV, and dispersed camping sites are generally up for grabs through December 15, but do your research ahead of time lest you find yourself scrambling for shelter as the sun makes its frosty descent.

Bask in the solitude of the National Forest’s monstrous focal point, Garden of the Gods Wilderness (one of seven such wilderness areas in the park), before making a peaceful meander through the Shawnee Hills Wine Trail. The 35-mile scenic drive features 11 award-winning wineries dotted throughout rural countryside towns like Cobden, Alto Pass, and Pomona, with must-stops running the gamut from the multi-award-winning Blue Sky Vineyard to the up-and-coming Honker Hill Winery, which proudly produces all its wines using fruit grown onsite. All the wineries are currently open for indoor and outdoor seating—and even many double as romantic inns for unparalleled convenience—so bring your vax cards, and enjoy this nearly Rhode Island-sized getaway destination.

Grant Park in Galena
Grant Park in Galena | Nejdet Duzen/Shutterstock

Galena, Illinois

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 call this hamlet home.

If you're feeling more outdoorsy, Galena also offers plenty of incentives for the adventurous at heart including rafting trips along the Mississippi River, an excursion to the fun nearby ski resort of Chestnut Mountain, and a number of cool bluff hikes overlooking the Mighty Mississippi. Stay off General Grant's beaten path at the LeFevre Inn, nestled on 100 acres of land just outside of town. And to get your fill of fall foliage, some of your best bets include the historic Stagecoach Trail outside town and the nearby Apple River Canyon State Park.

Saugatuck/Douglas
Saugatuck/Douglas

Saugatuck, Michigan

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), where you can rent kayaks, cruise on sailboats, and kick back along 10 miles of prime Lake Michigan real estate. Sand dunes hikes also vie for your attention at this Hampton-style retreat—especially during the cooler months when the water grows choppy and the winds start to kick—but it’s Saugatuck’s arts scene that really sets it apart from the region’s numerous visually arresting beach towns.

Saugatuck/Douglas
Saugatuck/Douglas

Known as “the art coast of Michigan,” Saugatuck and the neighboring towns of Douglas and Fennville are home to dozens of 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 resort towns in America. While most famous for its summers, fall is an equally excellent time to visit with price-drops at fun-loving lodging options like queer mecca Dunes Resort and vintage roadside charmers like Pines Motorlodge And Cottages and Saugatuck Retro Resort Motel. A seasonal bounty of activities also awaits, including craft booze crawls, apple picking, harvest dinners at farm-to-table masters, and corn mazes—you know, all your autumn essentials. And since it’s just a hop, skip, and a jump from Chicago, you may as well enjoy the journey by ticking off all the boxes on this road trip bucket list.

Ridges Sanctuary
Ridges Sanctuary | Matt Sampson Photography/Shutterstock

Door County, Wisconsin

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 little villages situated on a beautiful 75-mile peninsula surrounded by the shimmering waters of Lake Michigan and Green Bay. With 53 public beaches, five state parks, and 300 miles of shoreline, there's a lot to like (and do) here. And while fall’s thinner crowds do make for a nice break from their more raucous summertime counterparts, you’d still be wise to explore some of the area’s lesser-known attractions such as the 7,000 acres of breezy open green space carefully watched over by the Door County Land Trust, or the peaceful lighthouse-strewn Ridges Sanctuary, prime territory for listening to nothing but the sound of leaves crunching beneath your feet. Additional hidden gems like Baileys Harbor Ridges County Park or the breathtaking Hotz Memorial Town Park teem with similar outdoorsy appeal.

Destination Door County
Destination Door County

Limit your interaction with other humans by opting for a carry-out meal from a wealth of excellent local restaurants (Wild Tomato is an absolute no-brainer), and be sure to book a stay at one of the area’s many waterfront resorts, rustic log cabins, and fairytale inns. The richly colored area is also dense with seasonal activities from beyond-cute pick-your-own orchards and roadside farm stands to country stores and farmers markets bursting with local produce.

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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 is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.