11 Unforgettable Fall Getaways From Chicago

Holland, Michigan

Holland is best known for its rich agricultural heritage and scenic farmlands, offering a unique blend of history and natural beauty along the shores of Lake Macatawa. Located just 150 miles from Chicago, it’s a convenient overnight escape with a scenic waterfront drive along Highway 196. The town’s appeal is enhanced by its festive community, hosting events like the Tulip Time Festival, Fall Fest in October, and the Holland Farmers Market, which operates until early December. The Windmill Island Gardens is one of the most vibrant destinations in Holland, with fields of flowers set against a lush forested backdrop. For those seeking relaxing fall vistas, the town’s center is dotted with parks like Kollen Park on the waterfront, the sprawling 30-acre Window on the Waterfront, and the charming Centennial Park, each offering colorful autumn scenery.

Galena, Illinois

Galena is a picture-perfect fall destination for those in Chicago or nearby cities, offering vibrant parks with colorful leaves and cozy spots for local food. The journey along Highway 20 adds to its appeal with stops like Elizabeth, home to the Highway 20 Brewing Company and the Chicago Great Western Railway Depot Museum. In Galena, visitors can enjoy hot air balloon rides with Galena On The Fly for stunning foliage views, explore the haunted history on Amelia's Galena Ghost Tours, or sip seasonal wines at Galena Cellars Vineyard and Winery. Don’t miss the Galena River Trail, ideal for hiking or biking, with picnic spots to unwind and take in the autumn beauty.

Saugatuck, Michigan

Saugatuck is a charming lakeside town on Michigan’s Art Coast, offering a relaxing mix of natural beauty and artistic culture. Located 147 miles away, visitors to Saugatuck will have the opportunity to stop along unique attractions like South Haven, learn about the region's maritime history at the Michigan Maritime Museum, and pass by Sarett NatureCenter located along Highway 196. The famous Oval Beach draws visitors with its serene shoreline, while the town’s creative heart beats through its renowned art galleries, such as Amazwi Contemporary Art and James Brandess Studios & Gallery, Inc., alongside unique shops showcasing local artisans, including The Pink Patio. Additionally, Saugatuck Dunes State Park adds to the town's appeal with its cool lake air, perfectly complementing trails framed by vibrant autumn colors.

Woodstock, Illinois

Woodstock blends historic charm with the vibrant beauty of fall foliage, creating a relaxing and memorable autumn atmosphere. Located just 66.9 miles from Chicago, it’s an ideal day-trip destination. Dufield Pond Conservation Area and Raintree Park come alive with colorful leaves, offering peaceful trails perfect for a crisp fall walk. All Seasons Orchard offers apple picking, a corn maze, and other family-friendly activities, making it a perfect spot to embrace the season. The Woodstock Square Historic District enhances the experience with cozy cafes and restaurants. For entertainment, the historic Woodstock Opera House hosts seasonal performances, adding a cultural touch to your visit. Additionally, the drive back to Chicago offers opportunities to explore charming communities along the way, like Crystal Lake, where Veteran Acres Park showcases vibrant fall colors and peaceful trails

Starved Rock State Park

Starved Rock State Park, just 95.6 miles from Chicago, provides an easy escape into nature, featuring breathtaking fall vistas and serene trails. The journey becomes even more enjoyable with a stop in Ottawa, home to the picturesque Buffalo Rock State Park and a vibrant main street filled with welcoming dining spots like The Lone Buffalo and The Beach House, which add flavourful charm to the adventure. Designated a historic landmark in 1960, Starved Rock rises 125 feet above the Illinois River, inviting explorers to climb 65 steps for a pinnacle view. Here, visitors can feel the crisp autumn breeze and admire the stunning contrast of shimmering waters and luminous forested landscapes. The park accommodates extended stays with developed picnic areas and hiking paths of varying difficulty, including French Canyon, Lover’s Leap, and Eagle Cliff Overlook.

Chain O’Lakes State Park

Chain O’Lakes State Park is a breathtaking fall destination, where vibrant foliage reflects off interconnected lakes, creating a picture-perfect setting for outdoor adventure and relaxation. The park offers boat rides through Grass, Marie, and Nippersink Lakes and accommodates group picnics with dedicated grounds. Outdoor enthusiasts can fish, hike, bike, and explore 8 miles of horseback riding trails, making it a sought-after spot for various seasonal activities. Located just 66.7 miles from Chicago, the park is a perfect midday escape. On your way, consider stopping in nearby Antioch, where the cozy Vegas Café serves hearty breakfasts and lunches, or explore Richmond, home to The Store, Oldies and Goodies, a sprawling antique shop with an impressive selection of treasures. These stops enhance the journey with small-town charm, delicious eats, and unique finds, making your fall excursion more memorable.

Michigan City, Indiana

Michigan City seamlessly combines cultural attractions with natural splendor, making it a captivating fall destination. Visitors can enjoy seasonal blooms, tranquil nature trails, and the serene aquatic vistas of Lake Michigan. Located just 3.2 miles from Indiana Dunes National Park, the city offers a perfect blend of outdoor escapes, vibrant parks, and a lively downtown. A visit to Friendship Botanic Gardens is a must in the fall, where colorful blossoms and peaceful trails highlight the season’s vibrant foliage. History enthusiasts can explore Barker Mansion with guided tours that uncover the area’s rich heritage. For picture-perfect lakefront views, Washington Park and Beach offer idyllic spots for picnics and leisurely shoreline strolls. The Michigan City Farmers Market enhances the autumn experience with its local produce, artisanal goods, and fall-inspired treats.

St. Joseph, Michigan

St. Joseph is a beach town located along the west coast of Michigan. It is beautified with a forestry landscape that qualifies it as a prime fall destination. Ranked the most romantic small town by The Detroit Press, St. Joseph’s mix of beachside charm and seasonal vibrance offers an idyllic fall retreat. Visitors can enjoy leisurely walks through Lions Park Beach, where the golden hues of fall frame Lake Michigan’s calm waves. Seasonal events, such as the Luminary Festival, transform the town’s center with glowing lights and festive activities, while Fall Fest showcases handcrafted goods and live music, perfectly capturing the warm spirit of autumn. For a deeper connection with nature, Grand Mere State Park, just a short drive from town, offers breathtaking views, tranquil forested paths, and dune trails, making it an essential stop for those looking to fully embrace the season.

Elkhart Lake, Wisconsin

Elkhart Lake, Wisconsin, located 149.9 miles from Chicago, is a serene fall retreat with vibrant landscapes and small-town charm. This quaint village of 971 residents is surrounded by lush greenery. Highlights include the lake’s clear waters reflecting fiery autumn hues and the LaBudde Creek Segment of the Ice Age Trail in Kettle Moraine State Forest, offering breathtaking views of the colorful canopy. In town, charming streets feature community markets like Elkhart Lake’s Farmers Market and cozy dining spots like The Paddock Club, known for its seasonal menu, or Off the Rail Café with fresh, local dishes. Fall events like Elktoberfest bring music and festivities to the atmosphere. The journey to Elkhart Lake adds to its appeal with engaging stops along the way at other charming towns like Woodstock, and its All Seasons Orchard and Apple Holler near Milwaukee for pumpkin picking.

Soul Farm Retreats

Soul Farm Retreats, located 101.9 miles west of Chicago, offers a tranquil getaway where nature, yoga, and equestrian experiences beautify the fall getaway experience with a wholesome ambiance focused on relaxing and regrouping. The retreat is located in the rural town of Amboy, 7.8 miles from Amboy Marsh Nature Preserve, which also stands out for its untouched 302-acre sanctuary featuring rare habitats like oak sand savannas, sedge meadows, and seasonal wetlands, making it a haven for biodiversity. Visitors can enjoy hiking, bird-watching, and photography along sandy trails, a complimentary opportunity to connect with nature. Set on a historic family farm, the Soul Farm Retreat, enhanced with glamping tents, creates an intimate connection with the natural world through guided yoga sessions and unique equine interactions. Visitors can enjoy farm-to-table meals served in rustic elegance or unwind with meditative walks through private woodlands.

Camp Aramoni, Illinois

Finally, one of the most memorable and naturally indulgent fall escapes is an overnight stay at Camp Aramoni, where the rugged camping experience is made more enjoyable with a sense of luxury. Situated near Starved Rock State Park, located 98.6 miles southwest of Chicago, Camp Aramoni is a boutique campground offering a unique glamping experience. Spanning 96 acres, these campgrounds provide an opportunity to connect with nature on a deeper level, with surrounding woodlands, nearby hiking trails, and relaxing campfires under the stars. For adventures beyond the campgrounds, visitors can explore Starved Rock State Park, just 7 miles away, where glacier-carved sandstone canyons create dramatic landscapes. In the fall, vibrant foliage blankets the cliffs, offering stunning views from overlooks like Lover’s Leap and Eagle Cliff, while flowing waterfalls add a serene touch to the season’s beauty.

From the fiery foliage of Starved Rock State Park to the charming streets of Galena and the serene shores of St. Joseph, each destination promises a unique way to embrace the season. Whether you’re enjoying local festivals, exploring scenic trails, or simply relaxing amidst autumn’s glow, these fall escapes near Chicago capture the essence of fall and promise a memorable experience for visitors of all interests and appeals.