The Ultimate Chicago to Saugatuck Road Trip Itinerary

Chicago's towering skyscrapers and bustling streets feel worlds apart from the tranquil shores and artsy charm of Saugatuck, Michigan. But that's exactly what makes this road trip so magical. As a seasoned road tripper and adventure tour operator, I've driven this route more times than I can count, and it never fails to amaze me how much diversity you can pack into just 139 miles.

This journey takes you from the heart of the Midwest's largest city to a quaint beach town known as the "Art Coast of Michigan." Along the way, you'll cruise past stunning Lake Michigan vistas, climb towering sand dunes, explore charming lakeside communities, and immerse yourself in nature's beauty. It's a perfect blend of urban excitement, small-town charm, and outdoor adventure.

So buckle up, roll down the windows, and get ready for an unforgettable road trip from the Windy City to the shores of Lake Michigan. Whether you're a first-time visitor or a seasoned Midwest explorer, this itinerary will show you the best this route has to offer, with plenty of insider tips to make your journey truly special.

Explore Indiana Dunes National Park

Just an hour's drive from Chicago, Indiana Dunes National Park offers your first taste of Lake Michigan's stunning shoreline. This 15,000-acre park boasts 15 miles of sandy beaches, towering dunes, wetlands, prairies, and forests. Hike the Dune Succession Trail for a crash course in dune ecology, or brave the 3-dune challenge for a heart-pumping workout with rewarding views. After your hike, cool off with a swim in Lake Michigan's refreshing waters.

• Location: 1215 N State Road 49, Porter, IN 46304
• Best Time to Visit: Early morning for cooler temperatures and fewer crowds
• Duration: 2-3 hours

Why Stop Here: Experience the unique ecosystem of Lake Michigan's southern shore and enjoy breathtaking views from atop massive sand dunes.

Road Tripper's Tip: Pack a picnic to enjoy on the beach after your hike. The Portage Lakefront and Riverwalk area offers great facilities and a more secluded beach experience.

Discover Michigan City's Washington Park Beach

As you enter Michigan, make your first stop at Michigan City's Washington Park Beach. This expansive sandy beach offers a perfect place to stretch your legs and soak in Lake Michigan views. The park's claim to fame is its historic lighthouse, perched on a pier extending into the lake. Take a stroll along the pier for fantastic photo opportunities, especially at sunset when the lighthouse is beautifully illuminated.

• Location: 115 Lakeshore Drive, Michigan City, IN 46360
• Best Time to Visit: Late afternoon for the best lighting
• Duration: 1-2 hours

Why Stop Here: Capture iconic lighthouse photos and enjoy a classic Lake Michigan beach experience.

Road Tripper's Tip: Bring quarters for the parking meters, and arrive early on summer weekends to secure a spot.

Taste Wine at Round Barn Estate

As you continue north, take a slight detour inland to Round Barn Estate. This unique winery, distillery, and brewery is housed in a stunning Amish-built round barn relocated from Rochester, Indiana. Sample their award-winning wines, craft beers, and spirits while enjoying the picturesque vineyard views. Don't miss their signature DiVine Vodka, made from grapes grown on the estate.

• Location: 10983 Hills Rd, Baroda, MI 49101
• Best Time to Visit: Weekday afternoons for a more intimate experience
• Duration: 1-2 hours

Why Stop Here: Experience the burgeoning Southwest Michigan wine scene in a unique, historic setting.

Road Tripper's Tip: Designate a driver or consider staying nearby to fully enjoy the tasting experience. The nearby town of Baroda offers charming B&Bs.

Climb the Dunes at Warren Dunes State Park

Warren Dunes State Park is home to some of the most impressive sand dunes on Lake Michigan's eastern shore. The park's star attraction is the 260-foot-tall dune formation that offers panoramic views of the lake and surrounding forest. Climb to the top for a workout that rewards you with breathtaking vistas, then run or roll down for a thrilling descent. The park also features three miles of sandy beach perfect for swimming and sunbathing.

• Location: 12032 Red Arrow Highway, Sawyer, MI 49125
• Best Time to Visit: Early morning or late afternoon to avoid the midday heat
• Duration: 2-3 hours

Why Stop Here: Experience the thrill of climbing and descending massive sand dunes with stunning lake views.

Road Tripper's Tip: Bring plenty of water and wear sturdy shoes for the dune climb. The sand can get extremely hot in the summer!

Savor Fresh Fruit at Jollay Orchards

Michigan's fertile soil and lakeside climate create perfect conditions for growing delicious fruit. Experience this firsthand at Jollay Orchards, a family-owned farm that's been operating for over 160 years. Depending on the season, you can pick your own cherries, peaches, apples, or pumpkins. Don't miss their famous fruit-filled doughnuts, a local favorite that's worth every calorie.

• Location: 1850 Friday Rd, Coloma, MI 49038
• Best Time to Visit: Late summer for the widest variety of fruits
• Duration: 1-2 hours

Why Stop Here: Taste the freshest seasonal fruits and experience Michigan's agricultural heritage.

Road Tripper's Tip: Check their website or call ahead to see what's in season for picking. The farm also offers hayrides and a corn maze in the fall.

Explore Downtown St. Joseph

Known as the "Riviera of the Midwest," St. Joseph is a charming lakeside town that's perfect for a leisurely stroll. Start at the Whirlpool Compass Fountain, an interactive water feature that's a hit with kids and adults alike. Walk along the bluff for stunning lake views, then head down to Silver Beach for some sun and sand. Don't miss the Silver Beach Carousel, a beautifully restored merry-go-round that's been delighting visitors for over a century.

• Location: Downtown St. Joseph, MI 49085
• Best Time to Visit: Late afternoon to catch the sunset
• Duration: 2-3 hours

Why Stop Here: Experience a quintessential Lake Michigan beach town with a perfect blend of history and modern attractions.

Road Tripper's Tip: Park at Silver Beach and walk up to downtown. It's a bit of a climb, but you'll be rewarded with great views and you won't have to worry about downtown parking.

Visit the Curious Kids' Museum

If you're traveling with children (or are a kid at heart), don't miss the Curious Kids' Museum. This hands-on museum offers over 100 interactive exhibits that make learning about science, technology, and culture fun. Kids can climb aboard a real Coast Guard boat, explore a giant bubble tower, or try their hand at being a TV weather forecaster. It's a perfect place to break up the drive and let kids burn off some energy.

• Location: 415 Lake Blvd, St. Joseph, MI 49085
• Best Time to Visit: Weekday mornings tend to be less crowded
• Duration: 1-2 hours

Why Stop Here: Engage curious minds with hands-on learning experiences in a fun, interactive environment.

Road Tripper's Tip: Combine your visit with a trip to the nearby Curious Kids' Discovery Zone on Silver Beach for even more interactive fun.

Take a Detour to Fernwood Botanical Garden

For a peaceful break from the road, take a short detour to Fernwood Botanical Garden. This 105-acre property features beautiful gardens, natural areas, and an arboretum. Stroll through the Japanese-inspired garden, explore the tallgrass prairie, or walk the trails through beech-maple forests. The garden's diverse plant collections and tranquil atmosphere make it a refreshing stop on your journey.

• Location: 13988 Range Line Rd, Niles, MI 49120
• Best Time to Visit: Spring for blooming flowers or fall for autumn colors
• Duration: 1-2 hours

Why Stop Here: Immerse yourself in nature and enjoy a moment of tranquility in beautifully curated gardens.

Road Tripper's Tip: Check their event calendar before your visit. Fernwood often hosts plant sales, art exhibitions, and educational programs.

Sample Craft Beer at The Livery

Michigan is known for its craft beer scene, and The Livery in Benton Harbor is a standout brewery. Housed in a restored 1905 horse livery, this microbrewery offers a rotating selection of unique, hand-forged ales and lagers. Try their famous Trippel Weizenbock or the McGilligan's IPA. The Livery also features live music on weekends and a menu of wood-fired pizzas that pair perfectly with their brews.

• Location: 190 5th St, Benton Harbor, MI 49022
• Best Time to Visit: Friday or Saturday evening for live music
• Duration: 1-2 hours

Why Stop Here: Experience Michigan's renowned craft beer scene in a historic, atmospheric setting.

Road Tripper's Tip: If you're not a beer drinker, try their house-made sodas or ciders. Don't forget to grab a growler of your favorite brew to enjoy later in your trip.

Hike the Black River Preserve

As you approach South Haven, take a break to stretch your legs at the Black River Preserve. This 122-acre nature preserve offers hiking trails through mature forests and along the scenic Black River. The 2.5-mile loop trail provides a moderate hike with beautiful river views and opportunities to spot local wildlife. In spring, the forest floor comes alive with a carpet of wildflowers.

• Location: 2nd Ave, South Haven, MI 49090
• Best Time to Visit: Early morning for the best chance of wildlife sightings
• Duration: 1-2 hours

Why Stop Here: Immerse yourself in Michigan's natural beauty and enjoy a peaceful riverside hike.

Road Tripper's Tip: Wear sturdy shoes and bring bug spray, especially in the summer months. The trail can be muddy after rain, so check conditions before you go.

Explore Downtown South Haven

South Haven is a picturesque beach town that's worth a longer stop. Start your visit at the Michigan Maritime Museum, where you can learn about the area's rich nautical history and even take a sail on a replica 19th-century tall ship. Stroll down the charming downtown, lined with unique shops and galleries. Don't miss the South Haven Light, a historic lighthouse at the end of a long pier – it's one of the most photographed spots in town.

• Location: Downtown South Haven, MI 49090
• Best Time to Visit: Late afternoon to catch the sunset at the lighthouse
• Duration: 2-3 hours

Why Stop Here: Experience the charm of a classic Lake Michigan beach town with a rich maritime history.

Road Tripper's Tip: If you're visiting in August, try to catch the National Blueberry Festival, a celebration of the area's famous crop.

Indulge at Sherman's Dairy Bar

No trip to South Haven is complete without a stop at Sherman's Dairy Bar. This local institution has been serving up generous scoops of homemade ice cream since 1916. With over 50 flavors to choose from, including unique options like Grasshopper (mint ice cream with Oreos) and Chocolate Malt Supreme, you're sure to find a new favorite. The portions are famously huge, so consider sharing or opting for a single scoop.

• Location: 1601 Phoenix St, South Haven, MI 49090
• Best Time to Visit: Early evening for a pre-dinner treat
• Duration: 30 minutes to 1 hour

Why Stop Here: Taste some of the best homemade ice cream in Michigan in ridiculously generous portions.

Road Tripper's Tip: Try the Blue Moon flavor – it's a local favorite and a vibrant blue color that kids love.

Visit Fenn Valley Vineyards

As you continue north, make a stop at Fenn Valley Vineyards. This family-owned winery has been producing award-winning wines since 1973. Take a tour of the vineyards and winery to learn about the wine-making process, then enjoy a tasting of their diverse selection. From crisp Rieslings to bold Cabernet Francs, Fenn Valley showcases the best of Michigan wines. Don't miss their popular Capriccio, a sweet red wine that's perfect for summer sipping.

• Location: 6130 122nd Ave, Fennville, MI 49408
• Best Time to Visit: Weekday afternoons for a more personalized experience
• Duration: 1-2 hours

Why Stop Here: Discover Michigan's underrated wine scene and enjoy tastings with beautiful vineyard views.

Road Tripper's Tip: Check their events calendar – Fenn Valley often hosts fun wine and food pairing events or live music on weekends.

Pick Fruit at Crane Orchards

Just a short drive from Fenn Valley, you'll find Crane Orchards, a family-friendly farm where you can pick your own fruit. Depending on the season, you might find apples, peaches, blueberries, or pumpkins ripe for the picking. The orchard also features a corn maze in the fall and offers tractor rides for a full farm experience. Don't leave without trying one of their famous pies – the cherry crumb is a local favorite.

• Location: 6054 124th Ave, Fennville, MI 49408
• Best Time to Visit: September-October for apple picking and fall activities
• Duration: 1-2 hours

Why Stop Here: Experience the joy of picking your own fresh fruit and enjoy classic farm activities.

Road Tripper's Tip: Bring cash, as some farm stand purchases are cash only. Wear comfortable shoes you don't mind getting a bit muddy.

Explore Saugatuck Dunes State Park

As you approach Saugatuck, take some time to explore Saugatuck Dunes State Park. This 1,000-acre park features 2.5 miles of secluded Lake Michigan beach and coastal dunes that reach up to 200 feet tall. Hike the 5.5-mile trail system through wooded dunes and along the lakeshore for stunning views and a sense of peaceful isolation. The beach here is less crowded than in town, offering a more serene Lake Michigan experience.

• Location: 6575 138th Ave, Holland, MI 49423
• Best Time to Visit: Early morning for the best chance of having the beach to yourself
• Duration: 2-3 hours

Why Stop Here: Experience the natural beauty of Lake Michigan's dunes and enjoy a peaceful, less crowded beach.

Road Tripper's Tip: The hike to the beach is about a mile from the parking lot, so come prepared with water and anything you'll need for your beach time.

Ride the Saugatuck Chain Ferry

Upon reaching Saugatuck, start your visit with a unique experience – a ride on the Saugatuck Chain Ferry. This hand-cranked ferry is the only one of its kind still operating in the United States. The short trip across the Kalamazoo River offers great views of the harbor and is a fun way to reach Oval Beach. It's more than just transportation; it's a charming nod to Saugatuck's history and a must-do experience for any visitor.

• Location: 730 Water St, Saugatuck, MI 49453
• Best Time to Visit: Mid-morning before the day gets too hot
• Duration: 5-10 minutes for the crossing

Why Stop Here: Experience a unique piece of living history and enjoy scenic harbor views.

Road Tripper's Tip: The ferry is cash only, so make sure you have a few dollar bills on hand. It's a short ride, but a memorable one!

Relax on Oval Beach

Oval Beach is the jewel in Saugatuck's crown, consistently ranked as one of the best beaches in the world. With its soft sand, clear water, and backdrop of rolling dunes, it's easy to see why. Spend some time swimming, sunbathing, or beach combing. The sunsets here are legendary, painting the sky in vibrant oranges and pinks reflected in Lake Michigan's waters.

• Location: Perryman St & Oval Beach Dr, Saugatuck, MI 49453
• Best Time to Visit: Late afternoon for swimming and staying for sunset
• Duration: 2-3 hours or more

Why Stop Here: Experience one of the world's best beaches and witness a breathtaking Lake Michigan sunset.

Road Tripper's Tip: Parking can be limited on busy summer weekends. Consider taking the Saugatuck Dune Rides to the beach for a fun alternative.

Climb Mount Baldhead

For a bird's eye view of Saugatuck and the surrounding area, tackle the climb up Mount Baldhead. This large sand dune features a stairway of 302 steps leading to its summit. The climb is steep but short, and the panoramic views from the top are well worth the effort. You'll see Oval Beach, the Kalamazoo River, and the town of Saugatuck spread out before you.

• Location: Mt Baldhead Park, Saugatuck, MI 49453
• Best Time to Visit: Early morning for cooler temperatures and great lighting
• Duration: 30 minutes to 1 hour

Why Stop Here: Gain a new perspective on Saugatuck's geography and enjoy stunning panoramic views.

Road Tripper's Tip: Bring water and take your time on the climb. Once at the top, you can take a trail down to Oval Beach for a rewarding cool-off.

Explore Saugatuck's Art Galleries

Saugatuck isn't called the "Art Coast of Michigan" for nothing. The town is home to numerous galleries showcasing works from local and national artists. Start your art tour at the Saugatuck Center for the Arts, which features rotating exhibits and performances. Then, stroll down Butler Street, popping into galleries like Good Goods and James Brandess Studios & Gallery. You might just find the perfect artistic souvenir to remember your trip.

• Location: Downtown Saugatuck, MI 49453
• Best Time to Visit: Friday evenings when many galleries host openings or events
• Duration: 2-3 hours

Why Stop Here: Immerse yourself in Saugatuck's vibrant art scene and maybe take home a unique piece.

Road Tripper's Tip: Pick up a gallery guide at the visitor center for a comprehensive list of local art spaces.

Take a Saugatuck Dune Ride

For a thrilling way to experience Saugatuck's famous dunes, hop on a Saugatuck Dune Ride. These 40-minute tours take you through the steep slopes and deep valleys of a private dune area in converted trucks. Your driver will share interesting facts about the dunes' geology and local history while you hold on for a bumpy, fun-filled ride. It's a unique way to see parts of the dunes that are otherwise inaccessible.

• Location: 6495 Blue Star Hwy, Saugatuck, MI 49453
• Best Time to Visit: Mid-morning before the day gets too hot
• Duration: 40 minutes

Why Stop Here: Experience the thrill of dune riding while learning about the area's unique ecosystem.

Road Tripper's Tip: Bring sunglasses and secure any loose items - it can get windy on the dunes!

Kayak the Kalamazoo River

For a peaceful way to explore Saugatuck's waterways, rent a kayak and paddle the Kalamazoo River. The calm waters are perfect for beginners, and you'll get a unique perspective of the town from the water. Paddle past picturesque cottages, under the old chain ferry, and if you're up for it, all the way to the river mouth at Lake Michigan. Keep an eye out for local wildlife, including herons and turtles sunning themselves on logs.

• Location: Big Lake Outfitters, 453 Water St, Saugatuck, MI 49453
• Best Time to Visit: Early morning for calm waters and wildlife sightings
• Duration: 2-3 hours

Why Stop Here: Enjoy a peaceful paddle and see Saugatuck from a different angle.

Road Tripper's Tip: Pack a waterproof bag for your phone to snap photos, and don't forget sunscreen and water.

Sample Local Brews at Saugatuck Brewing Company

Cap off your Saugatuck adventure with a visit to Saugatuck Brewing Company. This local brewery offers a wide range of craft beers, from their popular Oval Beach Blonde Ale to seasonal specialties. Take a tour to learn about the brewing process, then settle in for a tasting flight. The brewery also serves up tasty pub fare if you're feeling hungry. Don't miss their beer garden on a nice day - it's the perfect spot to relax and reflect on your road trip adventures.

• Location: 2948 Blue Star Hwy, Douglas, MI 49406
• Best Time to Visit: Late afternoon or early evening
• Duration: 1-2 hours

Why Stop Here: Taste locally crafted beers and unwind after your road trip journey.

Road Tripper's Tip: Try their "Brew on Premise" experience if you have time - you can craft your own beer to take home!

Your Day-by-Day Chicago to Saugatuck Road Trip Adventure

Now that we've explored the highlights of this epic road trip, let's put it all together into a 3-day adventure. Remember, this itinerary is flexible – feel free to adjust it based on your interests, energy levels, and how long you'd like to linger in each location.

Day 1: Chicago to St. Joseph

• Morning: Depart Chicago early to beat traffic
• Mid-morning: Explore Indiana Dunes National Park (50 miles, ~1 hour from Chicago)
  • Hike the Dune Succession Trail
  • Take a quick swim if weather permits
• Lunch: Picnic on the beach or grab a bite in Michigan City
• Afternoon: Visit Washington Park Beach in Michigan City (10 miles, ~15 minutes)
  • Walk the pier and see the lighthouse
• Late Afternoon: Stop at Round Barn Estate (35 miles, ~40 minutes)
  • Wine tasting and tour
• Evening: Arrive in St. Joseph (25 miles, ~30 minutes)
  • Dinner at Clementine's Too
  • Overnight in St. Joseph

Road Tripper's Tip: Fill up on gas before leaving Chicago, as prices tend to be higher in tourist areas along the lakeshore.

Day 2: St. Joseph to South Haven

• Morning: Explore downtown St. Joseph
  • Visit the Curious Kids' Museum
  • Walk along Silver Beach
• Lunch: Grab a bite at Silver Beach Pizza
• Afternoon: Head to Warren Dunes State Park (15 miles, ~20 minutes)
  • Climb the dunes and enjoy the beach
• Mid-Afternoon: Visit Fernwood Botanical Garden (20 miles, ~25 minutes)
• Evening: Drive to South Haven (30 miles, ~40 minutes)
  • Dinner at Clementine's
  • Ice cream at Sherman's Dairy Bar
  • Overnight in South Haven

Road Tripper's Tip: Pack a cooler for beach snacks and to bring home Michigan produce from roadside stands.

Day 3: South Haven to Saugatuck

• Morning: Explore downtown South Haven
  • Visit the Michigan Maritime Museum
  • Walk the pier to South Haven Light
• Late Morning: Drive to Fenn Valley Vineyards (15 miles, ~20 minutes)
  • Wine tasting and tour
• Lunch: Picnic at Fenn Valley or head to Crane Orchards (5 miles, ~10 minutes)
  • Pick seasonal fruit
• Afternoon: Drive to Saugatuck (15 miles, ~20 minutes)
  • Hike at Saugatuck Dunes State Park
• Late Afternoon: Explore downtown Saugatuck
  • Ride the Chain Ferry
  • Visit art galleries
• Evening: Relax at Oval Beach
  • Watch the sunset
  • Dinner at The Southerner
• Optional: End the night with a beer at Saugatuck Brewing Company

Road Tripper's Tip: Book accommodations in Saugatuck in advance, especially during peak summer season.

Wrapping Up Your Chicago to Saugatuck Road Trip

As you complete your journey from the urban jungle of Chicago to the artsy shores of Saugatuck, take a moment to reflect on the diverse experiences you've had. From climbing sand dunes to sipping local wines, from exploring charming lake towns to relaxing on world-class beaches, this road trip offers a perfect blend of adventure, relaxation, and cultural experiences.

Remember, the joy of a road trip is in the journey itself, so don't hesitate to make unexpected stops or detours along the way. Maybe you'll discover a hidden beach, a quirky roadside attraction, or a farm stand with the juiciest peaches you've ever tasted. These unplanned moments often become the most memorable parts of a trip.

As you plan your return journey (or your next adventure), consider taking a different route back to Chicago. The inland route through Kalamazoo and Battle Creek offers its own unique attractions, including the Air Zoo Aerospace & Science Museum and the original Kellogg's Cereal City.

Whether you're a first-time visitor to the region or a seasoned Midwest explorer, the Chicago to Saugatuck route showcases some of the best that Michigan and Indiana have to offer. From the natural beauty of the Lake Michigan shore to the warm hospitality of small-town America, this road trip is sure to leave you with lasting memories and a desire to return.

So pack your bags, cue up your road trip playlist, and hit the road. Adventure awaits on the shores of Lake Michigan!