Our research is editorially independent but we may earn a commission for purchases made through our links.

10 Best Road Trips From Chicago

If you live in Chicago you obviously have a long list of things to see and do at your doorstep, but it’s always fun to make an escape from the big city every once in a while. You don’t have to book a flight as there are some great road trips that can make for a fun weekend, week or even longer getaway. These are some of the best to embark on from the Windy City.

Saugatuck, Michigan Saugatuck, Michigan
Credit: Saugatuck, Michigan by © Robert Philip | Dreamstime.com

Saugatuck, Michigan

Saugatuck is an especially picturesque small town filled with art galleries featuring local artists, mom-and-pop restaurants, unique shops, and more, but the highlight is Saugatuck State Park. It features 14 miles of hiking trails that lead to 1,000 acres of rolling, wooded dunes that soar as high as 200 feet tall. It’s also home to two-and-a-half miles of secluded beach along Lake Michigan, accessed via a just over half-mile hike.

Lake Geneva, Wisconsin Lake Geneva, Wisconsin
Credit: Lake Geneva, Wisconsin by © Hannah Babiak | Dreamstime.com

Lake Geneva, Wisconsin

Lake Geneva is just 90 minutes away from Chicago, an ideal destination when you’re searching for a shorter road trip. Located on an eight-square-mile lake, you can look forward to walks on the 26-mile Geneva Lake Shore Path, an old Native American trail that extends the entire length of the shoreline with gorgeous views throughout, enjoy a romantic boat cruise or rent a boat for a memorable day on the water. In town, you’ll find a wide range of dining, shopping, and entertainment venues and spas for relaxing after a day of play.

Madison, Wisconsin Madison, Wisconsin
Credit: Madison, Wisconsin by © Sean Pavone | Dreamstime.com

Madison, Wisconsin

The city of Madison is about a 2.5-hour drive northwest of Chicago and offers plenty of family-friendly activities to enjoy. Crowds are fewer, and you’ll discover a fantastic culinary scene along with a wealth of cultural attractions like the Wisconsin Arboretum, the Chazen Museum of Art, the Madison Museum of Contemporary Art, and the Olbrich Botanical Gardens. Visit the local breweries, enjoy live music, and shop the Dane County’s Farmers’ Market on Saturday mornings from April through November.

South Haven, Michigan South Haven, Michigan
Credit: South Haven, Michigan by © Michael Deemer | Dreamstime.com

South Haven, Michigan

While it may be a small port city, South Haven is only two hours from Chicago, and it’s truly a haven, providing a tranquil beach retreat along Lake Michigan. The town itself is filled with restaurants and unique shops and also hosts the Michigan Maritime Museum and a world-renowned lighthouse that’s served as a guiding light to ships entering the Black River for well over a century. The beautiful sandy beach is the highlight here, a place where many come to soak up the sunshine and enjoy all sorts of water sports.

Milwaukee, Wisconsin Milwaukee, Wisconsin
Credit: Milwaukee, Wisconsin by © Sean Pavone | Dreamstime.com

Milwaukee, Wisconsin

Just two hours north of Chicago, Milwaukee offers lots of fun attractions without the big tourist crowds. It is a hot spot for gourmet dining experiences, theater, art museums and much more. Of course, it’s famous for its beer, with many different brewery tour options, so beer enthusiasts will have plenty to choose from. It’s free to visit the Haggerty Museum of Art with its classic and contemporary works, while Black Cat Alley hosts 30,000 square feet of outdoor space dedicated to local artists’ murals and street art. If you want to get active, consider paddling right through downtown to work off all that beer and delicious food. You can rent a kayak or bring your own and paddle down the Milwaukee River.

Starved Rock State Park - Utica, Illinois Waterfall at Starved Rock State Park
Credit: Waterfall at Starved Rock State Park by bigstock.com

Starved Rock State Park - Utica, Illinois

Starved Rock State Park is just 100 miles southwest of Chicago, offering an ideal spot to enjoy nature with more than a dozen sandstone canyons along with beautiful waterfalls that are especially powerful in the spring. After heavy rainfall – this is also the perfect time for viewing colorful wildflowers. No matter what the season is, hiking is fabulous here – walk through the tranquil forest, keeping an eye out for deer and birds, including bald eagles, along the way. If you visit during the fall, it’s filled with vibrant foliage; in winter, you can even go ice climbing.

Galena, Illinois Galena, Illinois
Credit: Galena, Illinois by Chuck Kime via Flickr

Galena, Illinois

A three-hour drive will bring you to Galena, named as one of TripAdvisor’s “Top 10 Charming Small Towns.” Look forward to strolling cobbled streets lined with historic mansions as well as all sorts of outdoor adventure nearby.  Take a rafting trip, hike the bluffs that overlook the Mississippi River, and during the chillier months of the year, hit the slopes at the nearby ski resort.

Mackinac Island, Michigan Mackinac Island
Credit: Mackinac Island by © Michael Deemer | Dreamstime.com

Mackinac Island, Michigan

Mackinac Island is ideal if you’re looking for a long road trip that will get you away from it all, and it’s well worth the drive. Plan for a little over six hours plus the half-hour ferry ride to discover this island tucked between the northern tip of Michigan and the Upper Peninsula. Especially peaceful, the island is car-free, with transport by horse-drawn carriage and bicycle. Hike the network of 71 miles of trails that wind through the woods and limestone outcroppings, or ride a bike on the scenic coastline while listening to the sounds of nature and taking in the spectacular sights.

Door County, Wisconsin Peninsula State Park in Door County
Credit: Peninsula State Park in Door County by © Stevengaertner | Dreamstime.com

Door County, Wisconsin

Just under 250 miles north of Chicago, sandwiched between Lake Michigan and Green Bay, Door County is famous for its family-friendly attractions and 300 miles of gorgeous shoreline. The “Cape Cod of the Midwest,” as it’s sometimes referred to, offers a wide range of water sports, including kayaking and paddle boarding, along with opportunities for hiking and visiting multiple lighthouses. Climb the 100 steps to the top of Cana Island Lighthouse in Bailey’s Harbor for an especially picturesque view from above. Walking along the rock-ledge shore, you can capture some postcard-perfect photos of the 1870s lighthouse. Throughout the peninsula, there are countless state parks, charming small towns, and roadside cherry stands to take advantage of. Bailey’s Harbor is a must for wine enthusiasts, home to Stone’s Throw Winery, which offers tastings and occasional live entertainment.

Carbondale, Illinois Inspiration Point provides a magnificent view of the Shawnee National Forest
Credit: Inspiration Point provides a magnificent view of the Shawnee National Forest by © Jason P Ross | Dreamstime.com

Carbondale, Illinois

It’s a 5.5-hour drive southwest to Carbondale, a college town that offers lots to do, including enjoying refreshing drinks at places like Hangar 9 and The Cellar, as well as dining on a mouthwatering meal at nearby 17th Street BBQ in Murphysboro, renowned for serving the very best in the state. The southern end of the city opens up to the Shawnee National Forest, home to many wineries as the start of the Shawnee Hills Wine Trail, which features a dozen vineyards in picturesque settings for wine tasting and dining. There are 14 parks in the area for exploring nature and enjoying active pursuits as well.

Travel Deals

$350 Off Custom Australia Journey w/ Air - Ends 4/30

$2999+

9-Day Southern Spain Tour | Save $1,000 Per Couple

$1929+

Caribbean Cruises Up to 45% Off + Up to $300 Credit

$249+

Air & 14-Day Enchanting New Zealand w/ 9 Tours

$5749+

15-Days - 5 Countries | Central Europe Guided Tour

$2399+

Custom Ireland Tour | 7 to 10-Nt B&Bs + Rental Car

QUOTE

Save $200 | Air & 8-Day Costa Rica Adventure w/ Car

$1099+

7-Day Heart of Ireland Tour - $100 off use TI-100HIR24

$1659+

Hyatt Ziva Cap Cana All-Incl. Resort | Dominican Republic

$442+ pp/pn

New England Cruises Up to 45% Off + Up to $300 Credit

$529+

Explore Anchorage's Local Flavor: Dining, Pubs, more

FREE

Air & 9-Day Spanish Escape w/ Daily Breakfast

$2199+

14-Day Eastern Europe Tour | Save $300 Per Couple

$3619+

14-Day Scandinavia Tour | Save $150 Per Couple

$2424+

Air & 12-Day New Zealand Vacation w/ 9 Tours

$4599+