The Best Luxury Hotels in Chesterton, IN from ￥13,993 in 2026

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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.

￥19,665

￥23,872 total

includes taxes & fees

Sep 22 - Sep 23

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Top Chesterton Hotel Reviews

Waterbird Lakeside Inn

10/10 Excellent

"The room was clean,balcony was neat, feed the fish and turtles, ac worked great, staff was nice and helpful, booked 4 days but only needed 1, but the hardest thing was to get a receipt, had to wait till 8 am but they said they could email BUTthat don't work for DOT, OTHER THAN THAT I'LL WILL BE BACK, ITS A LITTLE HIGH ON THE PRICE, BUT, NO BED BUGS , NO BREAKFAST, BUT THE ROOMS ARE VERRY NICE ,!!!!"

Ameristar Casino Hotel East Chicago

8/10 Good

"Everything was good except for the service during breakfast. The waiter took our order, came back about a half hour later and asked if we were ready to pay our bill. Never bought any food. We just left without eating."

Best Western Indian Oak

10/10 Excellent

"I had the best time ever. My service dog was with me and the staff was amazing with him being there I room was so clean. I loved my balcony. We did not want to leave it was amazing"

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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