Downtown Chesterton, Indiana

Discover shopping, dining, and accommodation in downtown Chesterton.

Moving to Chesterton?

Order a Free Relocation Guide
Plan your trip in Chesterton using Travique: AI Powered Planner

Shop Downtown

Shop With Friends

Invite Friends

Talk To Our AI-Agents

AI Agent

We are seeking partnerships with forward-thinking city officials and business leaders to replicate
their downtowns and launch immersive virtual cities together.

Shop Downtown Discount Card

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.

Learn More

Shop

Gen. Tech LLC

(219) 617-5187

131 Ivy Street

Chesterton, Indiana

Deal or Discount: Military Veterans Discounts Daily

Authentic Thai Food and Sushi.

Hotels

Hilton Garden Inn Chesterton

501 Gateway Boulevard

Chesterton, Indiana

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

Hotel Tips

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.

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

Things To Do

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.

Chesterton brings a custom fit every time a shoe is bought locally. Nothing beats the hands on experience of shoe shopping to add to your collection of Men's, Women's and Children's shoes. Try them on, walk around and make sure you have the best fit as every manufacturer is a bit different on sizing.

Chesterton helps you expand your skills and learn some new ways to expand your artisan flare? Sign up for classes at your kitchen supply store, yarn shop, art and craft shop and photo gallery. You'll be having great fun with your new friends as you you take on that next project.

Why Do You Love Downtown?

Roberta Gomes

it's so quaint!

BOB BLACKMAN

Just a fun place to visit.

Megan H.

I love being able to browse a variety of my favorite restaurants and bars, all within easy walking distance of convenient parking. Enjoying local fare and live music downtown after a grilling day at the office makes every day feel like the weekend.

Kathleen Zimmerman

I get the best of both worlds of big city living and upper peninsula awareness.

Richard Held

Unique shops.

Join our newsletter

Support Cancer Research

The American Cancer Society does not endorse any product or service.