Downtown Chesterton, Indiana

Discover shopping, dining, and accommodation in downtown Chesterton.

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ShopDowntown.org Discount Card Program

The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.

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Gen. Tech LLC

(219) 617-5187

131 Ivy Street

Chesterton, Indiana

Deal or Discount: Military Veterans Discounts Daily

Authentic Thai Food and Sushi.

Hotels

BEST WESTERN INDIAN OAK

558 Indian Boundary Road

Chesterton, Indiana

Econo Lodge Chesterton

713 Plaza Dr.

Chesterton, Indiana

Quality Inn

418 Council Road

Chesterton, Indiana

Hilton Garden Inn Chesterton

501 Gateway Boulevard

Chesterton, Indiana

Hotel Tips

Not all online booking systems are fully integrated with hotel reservations systems so there is a chance that smaller hotels are hand entering your stay from a fax machine which leaves room for errors. Book directly with hotel to avoid any problems and ask for a price match if you find a better price online.

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Things To Do

Chesterton has several options for shopping for specialty food items that are not found in regular grocery stores. Shops tailored for "foodies" offer tastings of the products as well as scheduled culinary classes to perfect your skills. Shop for infused oils, salts and spices from around the World!

Chesterton has a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.

Chesterton shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Why Do You Love Downtown?

Christy Richards

Because I love to shop local and the stores and owners make your visit welcoming inviting you to return again with a smile on their face.

Jeremy Holmes

Supporting small business downtown is a very real way to support your local community. Downtown businesses are locals, like us.

Kate O'Rorke

We love the amazing shops and restaurants. The city is so clean and everyone is friendly and welcoming.

Erin Lawless

The shops and bakery make it an appealing destination for people who want to keep small businesses going by enjoying those shops as well

Tammy Cooper

Downtowns are so cute and has a very relaxed inviting vibe that puts a smile on my face. In addition, downtown was so clean. It was fun visiting the unique shops and boutiques and everyone was very friendly. Our stroll around Lithia Park was beautiful and so peaceful. It truly is a gem. Lastly, we ate at 4 or 5 different restaurants that had great food and great service.

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