Chesterton(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Chesterton, Indiana, the top choice for families is Holiday Inn Express Chesterton, offering spacious family rooms, free breakfast, and proximity to Lake George Park—perfect for outdoor fun. For a more historic experience, consider The Historic Chesterton Inn, a beautifully restored 19th-century inn with vintage charm, located just minutes from Chesterton Public Library and ideal for exploring local heritage and small-town atmosphere.

The downtown district of Chesterton is the prime area for sightseeing, with walkable access to Chesterton City Hall, Historic Downtown District, and charming local eateries. Stay at boutique options like The Chesterton House Bed & Breakfast, which offers guided local tours and is steps away from railway history sites and Victorian-era architecture, giving you an authentic taste of the town’s rich past.

Each summer, Chesterton hosts the Heritage Festival, celebrating its 19th-century agricultural roots and traditional crafts. Visitors can explore historic farming tools, enjoy folk music performances, and join hands-on pottery workshops. Don’t miss the Chesterton Historical Society Museum, which houses rare artifacts detailing early immigrant life in northern Indiana, offering deep insight into the town’s founding era.

The Chesterton Water Tower, with its iconic red brick dome and classic design, is one of the most photographed landmarks in town. Another favorite is St. Mary’s Church, featuring striking Gothic spires and stained-glass windows that glow in sunlight. The Chesterton Riverwalk Trail, a scenic path along the river, also offers stunning photo opportunities blending natural beauty with small-town charm.

Yes, some premium accommodations like The Chesterton House Bed & Breakfast provide pre-booked airport shuttles to Gary International Airport (GRR) and South Bend Regional Airport (SBN), requiring a 24-hour notice. While most downtown hotels don’t have scheduled shuttles, they can assist with car rentals or ride-sharing bookings to ensure seamless travel arrangements.

Try the signature fried chicken burger and homemade apple pie at Chesterton Diner, sourced from nearby farms. For a fusion twist, visit Barnyard Bistro, where Midwestern comfort food meets French culinary finesse—highlighting slow-cooked beef and seasonal vegetables. On Saturdays, don’t miss the Chesterton Farmers Market, offering fresh-baked breads, jams, and artisanal goods straight from local producers.

Absolutely. Chesterton is ideal for road trips, with clear streets and easy access to I-65 Highway, connecting quickly to Chicago and South Bend. Ample parking is available at hotels and attractions. Driving allows convenient access to nearby gems like Pleasant Lake State Park and Duneland Beach, perfect for lakeside relaxation and scenic drives.

For couples seeking romance, The Chesterton House Bed & Breakfast offers private fireplaces, secluded balconies overlooking oak trees, and customized candlelit dinner packages. Nearby, Riverfront Lodge features lake-view suites with hot tubs and panoramic glass walls—ideal for intimate evenings while watching sunsets over the Chesterton Riverwalk.

The peak season runs from late spring to early fall (May–September), when the weather is pleasant and outdoor events thrive. Major highlights include the Heritage Festival in June and the Riverfront Music Series in August. Winter months bring quieter charm with snowscapes and holiday lights, appealing to travelers seeking peaceful retreats.

Yes, several hotels welcome pets. Options like Holiday Inn Express Chesterton and The Chesterton House Bed & Breakfast offer pet-friendly rooms for a small fee ($25 per night). Amenities include pet beds, bowls, and maps to nearby dog parks. Always confirm availability in advance to avoid disappointment.