Great Lakes Road Trip Itinerary: 7 Days of Adventure, Scenery, and Small-Town Charm

So, you’ve got the itch for a road trip and want something a little different than just another highway adventure? Let me pitch you this: a Great Lakes road trip. Picture winding coastal drives, quirky little towns, lighthouse photo ops, fresh-caught fish dinners, and sunsets that look like they were stolen straight from an art gallery. Sounds dreamy, right?

I’m going to lay out a 7-day Great Lakes road trip itinerary that mixes scenic drives, fun cities, hidden gems, and plenty of time to just chill by the water. You can tweak it based on your starting point, but this route works great if you’re beginning in Chicago (because, let’s be honest, O’Hare is where a lot of trips begin).

Day 1: Chicago to Milwaukee – Lake Michigan’s Southern Edge

Distance: ~90 miles, 1.5–2 hours

Start with a morning in Chicago. Grab some deep-dish pizza to-go (yes, even at 10 a.m.—you’ll thank me later), then hop on I-94 north. Your first big stop? Milwaukee, perched right on the shore of Lake Michigan.

Milwaukee’s got this cool mix of history and hipster vibes. Check out the Milwaukee Art Museum (that wing-shaped building is Instagram gold), stroll along the RiverWalk, and maybe tour a brewery. Lakefront Brewery is a fan favorite, and you can sip while staring at the water.

End the evening with dinner by the lake. If you’re into fish fry (a Midwest classic), Friday nights in Milwaukee are legendary for it.

Day 2: Milwaukee to Door County – Small Towns & Cherry Pies

Distance: ~160 miles, 3 hours

Now the fun really begins. Head northeast toward Door County, Wisconsin’s answer to Cape Cod. It’s this skinny peninsula sticking out into Lake Michigan, and it’s adorable in the best possible way.

Door County is dotted with small towns—Fish Creek, Egg Harbor, Sister Bay—that feel like they were built for road-trippers. Spend the day hopping from one to another. Eat cherry pie, kayak the shoreline, or check out Cave Point County Park for dramatic limestone cliffs.

At night, catch a sunset in Ephraim or Sister Bay. Seriously, they put on a show.

Day 3: Door County to Mackinac Island – Ferry Time

Distance: ~280 miles, 5–6 hours (plus ferry)

This is a longer drive day, but it’s worth it. Head north through Wisconsin, cross the Upper Peninsula of Michigan, and make your way to Mackinaw City. From there, hop on the ferry to Mackinac Island.

Now, Mackinac is a whole different world. No cars allowed—just horses, bikes, and your own two feet. Rent a bike and circle the island (it’s only 8 miles around), sample the famous fudge, and stay overnight if you can swing it. You’ll feel like you’ve stepped back in time.

Day 4: Mackinac Island to Traverse City – Wine Country Meets the Lake

Distance: ~150 miles, 3–4 hours

After a ferry ride back to the mainland, head south to Traverse City, one of Michigan’s gems. Known for cherries, beaches, and wineries, this spot will make you want to slow down.

Check out the Old Mission Peninsula for vineyards with lake views that will leave you speechless. Or, if you’re into something more adventurous, Sleeping Bear Dunes National Lakeshore is just a short drive west—massive sand dunes you can climb, with views that look like you’re staring out over the Caribbean. Can you imagine that in Michigan?

Day 5: Traverse City to Grand Rapids – City Vibes & Craft Beer

Distance: ~140 miles, 2.5 hours

Say goodbye to Traverse City and head toward Grand Rapids, Michigan’s craft beer capital. This is your city day. Explore art murals, stop into a few breweries (Founders Brewing is the big one, but there are dozens), and take a stroll through Frederik Meijer Gardens if you’re into a calmer vibe.

Grand Rapids is a good halfway stop before looping back toward Lake Michigan’s western shore.

Day 6: Grand Rapids to Indiana Dunes – Beaches & Sand Dunes

Distance: ~120 miles, 2.5 hours

Today you’re going to be surprised. When people think Indiana, they don’t usually think beaches—but Indiana Dunes National Park proves them wrong. The dunes are right on Lake Michigan, and the park is a perfect place for swimming, hiking, or just relaxing on the sand.

This stop also puts you right back near Chicago, but don’t rush—spend the night nearby so you can soak in the quieter side of Lake Michigan before heading back into city life.

Day 7: Back to Chicago – Full Circle

Distance: ~50 miles, 1 hour

And just like that, you’ve circled back to Chicago. Use your last day to explore something you missed on Day 1. Maybe a lakefront bike ride, a stroll through Millennium Park, or one more slice of deep dish. Because honestly, can there ever be too much pizza?

Road Trip Tips for the Great Lakes

Best time to go: Summer (June–September) is prime for warm weather and beach time, but fall brings incredible leaf colors.
Pack layers: Even in July, nights by the lakes can get chilly.
Take it slow: The drives aren’t super long, but the charm is in the stops. Don’t rush from A to B.
Local eats: Try the fish fries in Wisconsin, cherries in Traverse City, fudge on Mackinac, and yes—cheese curds everywhere.

Why This Great Lakes Itinerary Works

This route gives you a mix of big city energy, small-town charm, and pure natural beauty. You’ll see two states (Wisconsin and Michigan), dip into Indiana, and circle Lake Michigan while sneaking peeks of Lake Huron too.

Honestly, it’s the kind of trip that makes you feel like you’ve seen a whole slice of America in just one week.

What do you think? Ready to gas up the car and hit the road?