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. The resort is even offering contactless carry-out and delivery from its on-site general store. The Minocqua area is Nature's Original Water Park, offering the very best scenery, outdoor recreation, and fun attractions in northern Wisconsin. A favorite among vacationers young and old, generation after generation, the area has activities and events for every season in Vilas County. Make summer vacation memories that last a lifetime this summer in the Northwoods of Wisconsin. Vilas County is home to thousands of acres of public land and nearly 90 recreational trails open to hikers, bikers, ATVers, UTVers, and outdoor explorers of all kinds. With more than 1,300 glacial lakes and countless rivers and streams, Vilas County is the perfect place for swimming, boating, fishing, and paddling. Make unforgettable memories today—plan your trip to Vilas County.

Miles from Chicago: 311 miles northwest
Suggested round-trip time: 5.5-hour drive
Location: Wisconsin, United States

Tripadvisor Rating: 5/5

Elkhart Lake is a village in Sheboygan County, Wisconsin, United States, located in the northwestern part of the county within the Town of Rhine. The population was 967 at the 2010 census. There are several museums in Elkhart Lake, including the Elkhart Lake Depot Museum and Henschel's Indian Museum. The Elkhart Lake Depot Museum is a century-old railroad station that has original depot furnishings and local memorabilia. Henschel's Indian Museum is located on an archaeological dig site and has a collection of Indian copper, pottery, and artifacts that date back to 8,000 BC. In addition, the Victorian Village Theater is a 100-year-old theater where musicals, dinner theaters, and musicians perform.

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 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 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. Summer classics include brew tastings, water activities, hiking, and biking, and no one ever hated a sunny drive through Kettle Moraine.

Miles from Chicago: 150 miles north

Suggested round-trip time: 2.5-hour drive

Location: Sheboygan County, Wisconsin, United States

Tripadvisor Rating: 4.7/5

Getaway Barber Creek ranks 1st on the list of best road trips from Chicago. 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 glamping-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 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. Getaway is a unique company that offers cozy cabin rentals throughout the United States, most of which are tucked away in nature-rich forests and other beautiful oases that provide genuine rejuvenation. Great Lakes State residents will be thrilled to learn that one of Getaway’s cabins is tucked away right here in Michigan. When you choose to spend a night or two here, you’ll enjoy a woodsy atmosphere and convenient access to nearby attractions like Lake Michigan beaches, hiking trails, local eateries, and so much more.

Miles from Chicago: 133 miles

Suggested round-trip time: 2.5-hour drive

Tripadvisor Rating: 4.5/5

Wisconsin Dells is known not only for its killer adult-friendly water parks but also for the dells themselves; a magnificent gorge carved out by ancient glaciers, boasting mighty views of sandstone cliffs along the Wisconsin River. The Dells of the Wisconsin River State Natural Area encompasses 5 miles of trails along the curving river, and private boat tours will take you along the upper and lower dells where you can marvel at the landscape from a comfortable seat. The Dells of the Wisconsin River spread over a vast area of carved gorges and deep canyons that runs up the side of the waterways to the north of the city. With various lookout points and canyon rims closed for ecological reasons, the best way to visit is typically on a boat tour.

Adventurous visitors will go for the remoter area known as the Upper Dells, where vast ice-age rocks and glacial cliffs are the backdrops. Others go for the Lower Dells, where you'll navigate mossy boulders and learn all about the native Ho-Chunk people. The boat float will also give you the best views of enormous and unusual rock formations that are unique to the area. If that’s not enough, nearby Devil's Lake State Park in Baraboo has equal views worth seeing. Apart from literally an endless amount of theme parks and water parks, the town itself has many charming features that are perfect for a summer getaway, like quaint b&bs (Oak Hill and Cedar Lodge), tasty restaurants/ breweries, and plenty of options to get close to furry friends.

Noah's Ark is recognized as both the biggest waterpark in America and one of the best things to do with kids in Wisconsin Dells. It reigns as one of the largest water parks in the entire USA, sprawling across a whopping 70 acres of grounds on the edge of Lake Delton, around 10 minutes drive from downtown. Inside, the attractions range from heart-thumping to soothing. You've got high-octane slides like the twisting Raja, which resembles a king cobra in attack mode. Follow that with a 400-ft plunge down the Scorpion's Tail, or a session on artificial surf waves. Mini-golf and a 4D theatre are also at hand in Noah's Ark for those who prefer to stay dry.

Miles from Chicago: 213 miles northwest
Suggested round-trip time: 4-hour drive
Location: Wisconsin Dells, United States

Tripadvisor Rating: 4.5/5

Madison, Wisconsin is special because it has all the city parks, like quality restaurants and historic venues, while also being surrounded by a plethora of nature-filled activities from hiking, and biking, to fishing and boating. Hike until your heart's content amongst the green trails, and then order a martini from any of the vibing local bars. In Wisconsin, there are plenty of drivable country and lakeside 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 views from the tallest point of this region of Wisconsin.

Spend an evening at the Collins Recital Hall for a musical performance or a day walking through the Chazen Museum of Art before exploring the Allen Centennial Gardens outside. And check out hands-on science exhibits and events at the Discovery Building on-campus. After touring the interior of the dome-shaped capitol featuring art and mosaics, go up to the observation deck and enjoy 365-degree views of downtown. Then, grab a bite to eat at a tavern or farm-to-table gem near the capitol square. For more family fun, check out the polar bear exhibit at Henry Vilas Zoo and explore the Olbrich Botanical Gardens. Both attractions are open year-round. A day out on or near the water is always a good idea; cruise around Lake Mendota on a boat rental, enjoy one of the 12 beaches found in Madison, or go snowshoeing over the frozen lake in the wintertime.

Miles from Chicago: 147 miles northwest

Suggested round-trip time: 2.5-hour drive

Location: Wisconsin, Dane County, United States

Tripadvisor Rating: 4.5/5

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 sand-swept mounds along the lake’s shores, and have many trails wandering through dense woodland, serene prairie, and swampy wetland areas that will no doubt excite with their 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.

In the many years since the city's incorporation in 1836, Michigan City has grown to be a large, vibrant city. Attracting thousands of visitors to the Indiana Dunes and the Lake Michigan shoreline, this lakeside city boasts many attractions and other things to do, including breweries and wineries, galleries, boat tours, beaches, gardens, shopping, casino, and even a zoo! Visitors can choose from a variety of lodging options including hotels, cabins, inns, and campgrounds. A multitude of dining options is available, such as fine dining, lakefront restaurants, ethnic offerings, breweries, and popular national chain restaurants, as well as local favorites. Michigan City is home to many events and festivals. Enjoy the Great Lakes Grand Prix or the work of fine artists and craftspeople at the Lakefront Art Festival. Participate in a fishing tournament or listen to an outdoor concert. With the abundance of sporting, entertainment, historical, shopping, and fine arts options available in Michigan City, visitors are sure to find the perfect way to enjoy their stay.

Miles from Chicago: 60 miles southeast
Suggested round-trip time: 1-hour drive
Location: LaPorte County, Indiana, United States

Tripadvisor Rating: 4.5/5

Starved Rock State Park in Illinois ranks 5th on the list of best road trips from Chicago. 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 or tread alongside an expert on a guided hike tour. Wherever you stay though, there is plenty to do in and near Ottawa.

Now that winter is waning just the teeniest, tiniest bit, let’s reminisce. This part of central Illinois is unusually beautiful during the colder months, with a bounty of trails winding through pine forests, deep canyons, frozen waterfalls, and a slew of spectacular ice formations. Together, the three parks form a trifecta of outdoor bliss, where opportunities for hiking, cross country skiing, and in some parts, even ice climbing abound. And after you’ve had your fill of the great outdoors, you’ll find antique shops, gift boutiques, restaurants, museums, immersive entertainment, and leisure activities just a stone’s throw away, alongside boozy local gems like craft breweries and wineries—nothing beats the small town hospitality and charm around here.

Miles from Chicago: 94 miles southwest

Suggested round-trip time: 2-hour drive

Location: 2678 E 875th Rd, Oglesby, Illinois 61348, United States

Tripadvisor Rating: 4.5/5

There’s a reason why Lake Geneva has been Chicago’s number one vacation destination for generations. 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. Luckily, there are many ways to escape the 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.

Lake Geneva is well-known for its numerous luxurious resorts, stunning beaches, and natural beauty. What is this? Its storied past means that many old buildings and historic homes still exist there, where they have become some of the many Lake Geneva attractions. Lake Geneva reminds this Michigander of Traverse City minus the cherries, but it is much more affordable. This lake has been a popular tourist destination for well over two hundred years. The tourism infrastructure around the lake is excellent with a wide variety of hotels and restaurants, many activities, numerous cultural events and festivals, and many opportunities for sightseeing and entertainment. Thanks to its fabled history, Lake Geneva remains a desirable summer destination for both the affluent and the ordinary, who flock to the lake to gawk at the waterfront estates from the public Shore Path and watch newspapers being delivered to the sprawling mansions by boat.

Miles from Chicago: 80 miles northwest
Suggested round-trip time: 1.5-hour drive
Location: Walworth County, Wisconsin, United States

Tripadvisor Rating: 4.5/5

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 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, ziplining at the nearby ski resort 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. If you’re interested in a hike, some of your best bets include the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park. Galena Country has tastes from around the world. Artisan-inspired dishes from Italy, Japan, Greece, and France are featured at every corner, making this a destination foodies of all ages will enjoy. Farm-to-table hotspots boast local flavors and made-from-scratch dishes. Cozy bistros nestled throughout the county provide the perfect spot for fresh, gourmet brews and mouth-watering soups, sandwiches, and pastries. Plus, you can have a host of upscale, fine dining establishments where the chef comes out and greets you at your table. You can find the right recipe, ambiance, and flavors to satisfy your cravings in Galena.

Miles from Chicago: 164 miles northwest
Suggested round-trip time: 3-hour drive
Location: Jo Davies County, Illinois, United States

Tripadvisor Rating: 4.5/5

Zion lies along Lake Michigan, near the Wisconsin border. The area was originally inhabited by Potawatomi Indians. Zion was founded in 1900 by John Alexander Dowie, an evangelist originally from Scotland, as the headquarters of his Christian Catholic Church. Dowie envisioned that the city, founded on principles of racial equality, would be run in accordance with Christian ethics. The massive 8,000-seat Shiloh Tabernacle was completed in 1900 and became Zion’s religious center until it burned in 1937. Settlement began in 1901, and from its origins, the city was theocratically governed, with the church controlling all business activities. With few exceptions, streets in the city were named for biblical figures. Financial difficulties eventually led to Dowie’s ouster as general overseer; his successor was Wilbur Glenn Voliva.

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 savannah oak trees. The town itself has several humble local hotel accommodations, but this state park is best to experience as a camper, so dust off that tent, pick up a bundle of firewood, and get cozy beneath the summer night sky. After traversing the state park, there are also numerous nearby forest preserves and river trails to experience like Van Patten Wood, Des Plaines River Trail, and the Pine Dunes Forest Preserve. In 1907 the city and the church were forced into bankruptcy, but over the next 15 years, the church reacquired much of its prior holdings in the city. Voliva and the church remained in firm control of Zion until the mid-1930s when Voliva was removed from power, and the city subsequently welcomed new churches and industry. The Christian Catholic Church schools were closed in 1939, after which a modern educational system was developed.

Miles from Chicago: 46 miles north
Suggested round-trip time: 1.5-hour drive
Location: Lake County, Illinois, United States

Tripadvisor Rating: 4.5/5