Things to Do in Chesterton, Indiana

By VI | Disclosure: I use affiliate links

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Need a relaxing getaway near Lake Michigan? I always recommend heading to Chesterton! I’ve wandered its downtown streets, hiked through the dunes, and spent lazy afternoons by the lake—and I think you’ll fall for its small-town charm and natural beauty just like I did. Nestled next to Indiana Dunes National Park, Chesterton offers everything from outdoor adventures to cozy cafés. Whether you’re hiking, shopping, or just taking it slow, I’ve found this to be one of the most delightful escapes in the Midwest.

Chesterton, IN Highlights:

You’ve got to explore Indiana Dunes National Park—I’ve spent hours hiking dunes and walking along the beach, and the lake views never get old. With over 15,000 acres of trails and shoreline, there’s something for everyone.
If you’re visiting between May and October, don’t miss Chesterton’s European Market. I always make time to browse the fresh produce, local crafts, and live music—it’s such a fun weekend vibe.
For a peaceful walk, I head to Coffee Creek Watershed Preserve. You’ll love the boardwalks, quiet trails, and gardens. It’s my favorite spot to slow down and just take in the scenery.
Need a beach day? Indiana Dunes State Park is perfect. I’ve swam, picnicked, and even tackled the “Three Dune Challenge”—it’s a workout, but totally worth it for the views!
For local flavor, you’ve got to check out Historic Downtown Chesterton. I’ve found great little shops, galleries, and cafés while strolling the streets—you’ll feel right at home here.

Best Time to Visit Chesterton, IN

In my experience, the best time to visit Chesterton is from May through October. That’s when the weather’s ideal for beach days, hiking, and local festivals. I especially love coming in the fall—the foliage is gorgeous, and the trails are crisp and quiet.

How to Get to Chesterton, IN

Driving in? I usually take I-94 or the Indiana Toll Road (I-80/I-90). Chesterton’s just about an hour southeast of Chicago—easy and scenic.
Taking the train? You’ll want to hop on the South Shore Line. I’ve used the Dune Park Station nearby—it connects right to downtown Chicago and makes for a smooth, car-free trip.
Flying in? I’ve flown into both Midway and O'Hare—they’re about an hour to an hour and a half away by car. Either one works depending on where you’re coming from.

Where to Stay in Chesterton, IN

Spring House Inn: I’ve stayed here for a quiet retreat—it’s rustic, peaceful, and surrounded by woods. You’ll feel tucked away while still close to everything.
Hilton Garden Inn Chesterton: When I want something modern and convenient, I go here. You’ll have all the amenities, plus it’s close to the highways and parks.
Waterbird Lakeside Inn: I love the lake views at this one—it’s peaceful, scenic, and just a short drive from downtown. If you want something relaxing, this is it.