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 21 - Sep 22
Tomorrow
Sep 22 - Sep 23
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
￥18,620
￥22,735 total
includes taxes & fees
Oct 6 - Oct 7
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
"Our original room was in the old tower which needs a refresh. However, for a small fee they updated us to the newer tower which was terrific. It was very clean, well maintained and quiet. The casino itself was too smoky for me, and there were not that many food options."
Evan 1-night trip
Posted 9 hours ago
Blue Chip Casino Hotel and Spa
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

10/10 Excellent
"Excellent location for the dunes- helpful staff - good overall - a little expensive - its not "luxury"- but seems consistent with the area."
Laurel 2-night trip
Posted 13 hours ago
Quality Inn Chesterton near Indiana Dunes National Park I-94
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Nice hotel near lots of dining"
Sally 2-night trip
Posted 17 hours ago
Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Love this hotel! Staff is so friendly and helpful. I arrived at the hotel injured from a motorcycle accident that occurred on my way from NY to Colorado. The whole staff is so caring and kind. My room is lovely and comfortable. I am temporarily stranded due to the accident but so glad I chose this hotel to recuperate at."
Dina 1-night trip
Posted 2 days ago
Waterbird Lakeside Inn

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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