When the leaves start to turn and the air gets crisp, there’s nothing better than escaping the city for a weekend retreat. If you’re looking for the best Fall Getaways near Chicago, offer a perfect blend of vibrant foliage, cozy accommodations, and seasonal activities. From sipping cider at local orchards to hiking along the dunes of Lake Michigan, this region is an easy drive that feels like a true escape.

1. Scenic Drives Through Southwest Michigan

Fall color peaks between late September and mid-October, making Southwest Michigan one of the Midwest’s best fall getaways near Chicago. Take US-12 (the historic Old Sauk Trail) or Red Arrow Highway for tree-lined stretches bursting with orange, gold, and red. Don’t forget to stop at Warren Dunes State Park to climb the dunes and catch panoramic lake views framed by fall foliage.

As you plan your Fall Getaways near Chicago, consider visiting the stunning parks and natural spaces that showcase the season’s beauty.

Plan your trip with the Pure Michigan Fall Color Map or check live foliage updates at ExploreFall.com. For more inspiration, try a one-day road trip from New Buffalo during peak season.

2. Apple Orchards & Cider Mills

Nothing says autumn like apple picking. Just minutes from New Buffalo, you’ll find family-friendly orchards offering hayrides, pumpkin patches, and fresh donuts. Popular stops include Williams Orchard and Garwood Orchards in La Porte, or Fruit Acres Farm Market and Jollay Orchards up in Coloma. A cup of hot cider or a caramel apple makes the perfect seasonal treat during your Fall Getaway near Chicago.

For the ultimate autumn experience, discover more Fall Getaways near Chicago by exploring hidden gems in the region.

3. Wineries & Breweries

Southwest Michigan is wine country, and fall is harvest season. Cozy tasting rooms and hearty seasonal brews make this time of year especially inviting. Stop in at Journeyman Distillery for craft spirits, grab a pint at Beer Church Brewing in New Buffalo, or try seasonal pours at Zorn Brew Works in Michigan City, Greenbush Brewing in Sawyer, and Haymarket Taproom in Bridgman.

Wine tasting is a must during your Fall Getaways near Chicago. Enjoy scenic views paired with seasonal flavors.

For wine lovers, there’s no shortage of options. Tabor Hill Winery & Restaurant is a destination with vineyard views and an on-site restaurant. Solasta Winery, located across from Warren Dunes, is a boutique gem, while Dablon Vineyards offers elegant indoor and outdoor tasting spaces. Other favorites include 12 Corners Vineyards and Contessa Wine Cellars.

To make things effortless, guests at Copper Top Ridge can book a curated experience with Grape & Grain Tours, a wine and brewery tour service that takes you to some of the region’s best tasting rooms — no driving required.

4. Outdoor Adventures

Fall weather is ideal for exploring the outdoors during Fall Getaways near Chicago. The Galien River County Park boardwalk is perfect for birdwatching and wildlife spotting against colorful treetops. Bikers can follow trails that weave through charming small towns — check out our New Buffalo biking guide for local routes.

5. Explore Local Charm

Beyond orchards and wineries, Harbor Country offers plenty of small-town character. Spend an afternoon browsing boutique shops, art galleries, and cafés in downtown New Buffalo, where the vibe is both cozy and sophisticated.

Don’t miss out on the local charm that enhances your Fall Getaways near Chicago. Unique shops and cozy cafes await.

6. Cozy Nights at Copper Top Ridge

After a day of exploring Southwest Michigan, nothing beats unwinding in a private vacation rental. At Copper Top Ridge in New Buffalo, you can soak in the hot tub, relax by the fire pit, or curl up next to the fireplace. With space for friends and family, it’s the perfect Fall Getaway from Chicago — just 90 minutes from the city.

Your Fall Getaway near Chicago wouldn’t be complete without relaxing at the perfect vacation rental.

👉 Ready to plan your escape? Take a closer look at our vacation rental with hot tub & fire pit.

Planning your next Fall Getaways near Chicago? Start with a comfortable and inviting space.

🧳 What to Pack

• Warm layers and a cozy sweater

• Hiking shoes for trails and dunes

• A camera for fall foliage shots

• A bottle of local wine to enjoy by the fire pit

🛒 Recommended Gear for Your Fall Getaway

To make your trip even more comfortable, here are a few essentials we recommend (affiliate links — we may earn a small commission at no cost to you):

• Cozy Fall Picnic Blanket – Ideal for vineyard picnics, dune overlooks, or fireside lounging.

• Travel Thermos – Keeps cider or coffee hot while exploring trails or orchards.

• Waterproof Sand Dune Hiking Shoes – Perfect for tackling Warren Dunes or fall hikes.

• Women’s Packable Rain Jacket – Lightweight, waterproof, and reflective for crisp autumn days.

• Fujifilm Instax Mini 41 Instant Camera (Vintage) – Capture fall memories instantly with a retro touch.

• JBL Flip 7 Bluetooth Speaker – Bring your favorite music to the patio, fire pit, or hot tub.

Packing smart ensures your Fall Getaway near Chicago is both comfortable and memorable.

Remember, the right gear enhances your Fall Getaway near Chicago experience.

Whether you’re craving outdoor adventure, local wine and cider, or a cozy retreat with friends, Southwest Michigan has it all. For couples, families, or groups, fall is the perfect season to experience the charm of Harbor Country.

For unforgettable experiences, check out our favorite Fall Getaways near Chicago tailored for everyone.

👉 Book Your Fall Getaway at Copper Top Ridge

Your ideal Fall Getaways near Chicago are just a reservation away!