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 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chesterton luxury hotels

Lobby sitting area
Casino
Front of property
Lounge

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.
￥22,288
￥26,806 total
includes taxes & fees
Oct 5 - Oct 6
Ameristar Casino Hotel East Chicago
View all properties

Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"The Hotel and staffs are nice helpful. It's a blessing for those who enjoy alcoholic beverage, one can have some drinks on the casino and walk straight to your hotel room. However, this property is located at an industrial area. I do not recommend strolling beyound the hotel's property as its very dark, isolated and sketchy. This gives a completely difgerent perspective of Chicago and city vibes that one would be expecting from."
Ambarish 3-night trip
Posted 23 hours ago
Ameristar Casino Hotel East Chicago
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

10/10 Excellent
"Hair dryer was broke and AC water was leaking from the room upper room. The staff changed my room. It was ok."
Fernanda 1-night trip
Posted 23 hours ago
Baymont by Wyndham New Buffalo
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Really liked being lakeside and able to walk around outside without having to walk inside down halls. Friendly helpful staff too."
Robert 2-night trip
Posted 1 day ago
Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Amazing stay. The balcony view was amazing. The room was huge. I highly recommend!"
Michelle 3-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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