A wooden staircase ascending a sandy hill with sparse vegetation.

Find Luxury Hotels in Chesterton, IN

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Check availability on Chesterton Luxury Hotels

Tonight
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chesterton luxury hotels

Lobby sitting area
Lounge
Front of property
Casino

1. Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago
East Chicago
  • Art Deco elegance meets beachfront luxury with casino thrills, fine dining, and marina views.
￥22,272
￥26,787 total
includes taxes & fees
Oct 5 - Oct 6
Ameristar Casino Hotel East Chicago
View all properties

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"What ud expect from a casino hot"
Charles 1-night trip
Posted less than an hour ago
Blue Chip Casino Hotel and Spa
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Everything was perfect breakfast & cleanliness. Definitely would stay there again"
Marc 2-night trip
Posted 3 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"The grandchildren loved fishing from hotel balcony. Was alot of fun"
LeAnne 1-night trip
Posted 5 hours ago
Waterbird Lakeside Inn
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
"Ckean"
Jp 1-night trip
Posted 13 hours ago
Ameristar Casino Hotel East Chicago

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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