The Best Luxury Hotels in Chesterton, IN from ￥16,137 in 2026

A wooden staircase ascending a sandy hill with sparse vegetation.

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Our top choices for Chesterton luxury hotels

A modern lobby with a sofa, coffee table, and a fireplace.

A bar area with a counter, multiple TVs, and a seating area with chairs and tables.

A multi-story hotel with a prominent 'AMERISTAR' sign, featuring a modern architectural design with large windows and a flat roof.

A casino floor with multiple slot machines and a few blackjack tables.

1. Ameristar Casino Hotel East Chicago

East Chicago

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

￥16,571

￥20,470 total

includes taxes & fees

Aug 31 - Sep 1

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Top Chesterton Hotel Reviews

Microtel Inn & Suites by Wyndham Michigan City

10/10 Excellent

"We stayed here a week because we did not have power following the 8/11/26. The staff took care of us. It is a clean and safe place to stay. It’s no frills but it’s what we needed when we couldn’t be at home. Thank you all for the welcoming spirit and patience. The Gray Family"

Blue Chip Casino Hotel and Spa

8/10 Good

"There was no soap at the sink that was outside of the bathroom. Had to use the one in the shower. Otherwise everything was great and the food was fulfilling. Will stay there again hope the pool will be restored by then."

Best Western Indian Oak

8/10 Good

"Stay was good and close to the National Park, Chesterton downtown is a cute area. Pool was refreshing after a long day. Grab and go breakfast was decent."

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

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