Perfect Road Trips for When You Need to Escape Chicago

Take a break from it all.

To state the painfully obvious, it’s been a long year. At this point in the pandemic, after months of waves and spikes, it’s hard to know where to travel safely. Look at a map and pretty much every state is under a travel quarantine order, so if you don’t mind an additional two-week break from society when you get back, a nature-packed small town road trip remains your best option for 2020 travel. From well-known seasonal standbys to more remote wilderness gems, here are the best road trips from Chicago to help maintain (or recover) your sanity this fall. Be sure to check local Covid restrictions in your area—and wear a mask.

Lake Geneva
Thomas Barrat/Shutterstock

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 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. Be warned, however: it is extremely busy on summer weekends, although things do tend to chill out quite a bit in fall. Luckily, there are many ways to escape the still-crowded downtown from walking the entire length of the lake shore along the town’s uniquely open-to-the-public Lake Shore Path to hiding out in under-the-radar Lake Como, home of the epic Mars Resort and its newly expanded patio. The lesser-visited lakeside towns of Williams Bay, Fontana and nearby Lake Delavan are also more than worthy of exploration any time of year.

Stay: Find a great Airbnb near Lake Geneva

Ottawa, Illinois
Nicola Patterson/Shutterstock

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 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. Escape the crowds of leaf peepers this fall with a trip to see 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 their Fall Color Trolley Tour or Autumn on the River Cruise.

Stay: Find a great Airbnb near Starved Rock State Park

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 and paddleboat rides also vie for your attention at this Hampton-style retreat, but Saugatuck’s arts scene is what really sets it apart from the region’s numerous beach towns. 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. While most famous for its summers, fall is an equally excellent time to visit with a seasonal bounty of activities including craft booze tours, apple picking, harvest dinners, and corn mazes. You know, all your autumn essentials.

Stay: Find a great Airbnb near Saugatuck

Elkhart Lake, Wisconsin

Distance from Chicago: 150 miles north, 2.5-hour drive

This charming little hideaway about 30 minutes west of Sheboygan is often overlooked by those seeking the classic lake town experience, 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 and a famous nearby racetrack. The AAA Four Diamond Osthoff Resort is a popular choice on the lake, but the area also offers a wealth of social distancing-friendly 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 ride on the 17-mile Old Plank Road Trail, and be sure to spend some time cozied up on Elkhart Lake itself with a kayak, paddleboard, or on your keister enjoying the view from the Osthoff’s private beach or the public Fireman’s Park. Fall classics include pumpkin patches and brew tastings, and no one ever hated on a foliage-packed drive through Kettle Moraine.

Stay: Find a great Airbnb near Elkhart Lake

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 make his home here. If you're feeling more outdoorsy, Galena also offers plenty of activities for the adventurous 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. For fall foliage, some of your best bets include the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park.

Stay: Find a great Airbnb near Galena

Richland County, Wisconsin

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 tailor made for the age of coronavirus. Social distancing is no problem on the lush 80-acre property, which has no lobby or public gathering place. 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, grab a picnic with a bottle of wine in a grassy open field, or explore the 15-mile Pine River Recreation Trail by bike over an abandoned railroad line dotted with bridges. The area also boats three nearby rivers with 267 miles of Class I and Class II trout fishing plus five state parks within an hour’s drive, including the 100-mile Lower Wisconsin River Scenic Byway.

Stay: Find a great Airbnb in Richland County

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 great little towns 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 the thinner crowds of fall do make a nice break from their more raucous summer compatriots, you would still be wise to explore some of the area’s lesser-known 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 crushed leaves beneath your feet. Limit your interaction with other humans by doing carry-out from a wealth of excellent local restaurants such as Wild Tomato, and be sure to check out other hidden natural gems such as Baileys Harbor Ridges County Park or the breathtaking Hotz Memorial Town Park. The fall color-rich area is also dense with seasonal activities from beyond-cute cherry orchards and roadside farm stands to country stores and farmers markets.

Stay: Find a great Airbnb in Door County

Traverse City, MI
Doug Lemke/Shutterstock

Traverse City, Michigan

Distance from Chicago: 323 miles northeast, 5-hour drive

There’s no shortage of nice beaches near Chicago. Then again, there are no beaches quite like the absolutely stunning Sleeping Bear Dunes National Lakeshore. Yet one of the most gorgeous locations in the Midwest -- complete with 35 miles of scenic coastline, forests, dunes, bluffs, and plenty of massive mounds of sand to roll around in -- is not alone when it comes to eye-popping beach hopping near the charming resort town of Traverse City, located at Michigan’s northern tip. From the popular Clinch Park and Bryant Park beaches to the more remote Haserot and North Bar Lake beaches, stunning views of the Grand Traverse Bay await from a number of locations in town. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America -- and an absolute stunner in fall.

Stay: Find a great Airbnb in Traverse City

carbondale illionis
Shawnee National Forest | anthony heflin/shutterstock

Shawnee National Forest, Illinois

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. Unplug and 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. Most wineries are currently open for outdoor seating only, but you’ll have no problem social distancing in the nearly Rhode Island-sized national forest.

Stay: Find a great Airbnb near Shawnee National Forest

Vilas County, Wisconsin

Distance from Chicago: 311 miles northwest, 5.5-hour drive

If you’re looking for the great Wisconsin Northwoods experience you’ve only heard about by drinking at Will’s Northwoods Inn, it’s time to point your GPS towards under-the-radar Vilas County. With one of the world’s largest collections of freshwater lakes, this outdoor purist’s paradise boasts more than 1,300 lakes and 73 rivers and streams. 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 cabins and luxury glampsites to boat rentals on one of the finest musky fishing lakes in North America. Social distancing isn’t a problem on the gorgeous 15-acre wooded property, and the resort (run by former Chicagoans Darren and Genevieve Coady) is even offering contactless carry-out and delivery from its on-site general store.

Stay: Find a great Airbnb in Vilas County

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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.