The Best Luxury Hotels in Chesterton, IN from ￥13,726 in 2026

A wooden staircase ascending a sandy hill with sparse vegetation.

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Our top choices for Chesterton luxury hotels

1. Ameristar Casino Hotel East Chicago

East Chicago

Art Deco elegance meets beachfront luxury with casino thrills, fine dining, and marina views.

￥22,230

￥26,735 total

includes taxes & fees

Oct 6 - Oct 7

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Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

10/10 Excellent

"Wonderful hotel"

Blue Chip Casino Hotel and Spa

10/10 Excellent

"It was my first time only thing that it wasn’t a microwave in the room everything was Nice"

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent

"I did not like to see so many cannabis stores within walking distance of our hotel.."

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Chesterton?

Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesterton offers. Known for its restaurants, Chesterton also has some interesting things to see and do including Lake Michigan, so you may want to take in the local sights during your visit.

When can I expect good weather in Chesterton?

Planning for the weather is an important factor for making your trip to Chesterton a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.

What's there to see and do in Chesterton?

Enjoy Chesterton and visit Lake Michigan, Lustron House, and Indiana Dunes Visitor Center. If you have extra time while you're in the area, you might want to see Bailly Homestead - American Indians and Fur Traders and Indiana Dunes National Park.

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Find Luxury Hotels in Chesterton, IN

Change your mind

Treat yourself

Be picky

Check availability on Chesterton Luxury Hotels

Our top choices for Chesterton luxury hotels

1. Ameristar Casino Hotel East Chicago

Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

Blue Chip Casino Hotel and Spa

Holiday Inn Express & Suites New Buffalo by IHG

Frequently asked questions

Explore a world of travel with Expedia