The Best Luxury Hotels in Chesterton, IN from ￥13,964 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 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.

A modern hotel lobby with a coffee station, seating area, and a reception desk.

1. Ameristar Casino Hotel East Chicago

East Chicago

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

￥19,399

￥23,614 total

includes taxes & fees

Oct 5 - Oct 6

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Top Chesterton Hotel Reviews

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent

"Property is great, very helpful front desk staff. It is a short (under 5 minute) drive away from the 'town' area of New Buffalo (and the beach). Don't take the Amtrak to get here like we did though, there are no Lyfts/Ubers. And there is no sidewalk to walk from the property to the town and beach."

Blue Chip Casino Hotel and Spa

10/10 Excellent

"Clean room and clean casino had a great time"

Waterbird Lakeside Inn

8/10 Good

"Balcony chairs were old.. view is amazing, but chairs are old! Overall highly recommend staying here. Balcony needs TLC."

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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