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
Aug 16 - Aug 17
Tomorrow
Aug 17 - Aug 18
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Chesterton luxury hotels

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.
¥16,568
¥20,466 total
includes taxes & fees
Aug 30 - Aug 31
Ameristar Casino Hotel East Chicago
View all properties

Top Chesterton Hotel Reviews

Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"The hotel is a little older, but the room was super clean and large. We loved watching the turtles and the geese from the balcony! The parking was also convenient."
Robin 1-night trip
Posted less than an hour ago
Waterbird Lakeside Inn
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Arriving at the hotel Lisa at the front desk was very welcoming. So many guests were there due to the recent power outage from the tornado, and Lisa made the check-in process very smooth. The two queen beds are very spacious for a family of four. The only disappointment was when asked for more face towels and dry off towels we were told that it was a limit. My husband explained that it was only two towels of each in the room so we should at least get four towels for each guest that is booked in the room and then we were given an extra two towels."
Krystal 1-night trip
Posted 5 hours ago
Blue Chip Casino Hotel and Spa
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

8/10 Good
"Clean, comfortable room!"
Mara 3-night trip
Posted 11 hours ago
Baymont by Wyndham New Buffalo
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"The breakfast was great and we enjoyed the lake view. Didn’t get a chance to do much else because of the storm and the loss of electricity. That was the only reason we left early. We would definitely stay there again."
Susan 3-night trip
Posted 2 days ago
Best Western Indian Oak
Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

8/10 Good
"Good value for this hotel. Rooms were comfortable and clean. Breakfast included scrambled eggs and sausage as well as waffles and cold items. Not too far of I-94 so it was much less expensive to stay in Michigan City than closer to Chicago."
Robin 1-night trip
Posted 3 days ago
Microtel Inn & Suites by Wyndham Michigan City

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 Indiana Dunes State Park, 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, Indiana Dunes State Park, and Lake Michigan. If you have extra time while you're in the area, you might want to see Lustron House and Indiana Dunes Visitor Center.

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