A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Aug 14 - Aug 15
Tomorrow
Aug 15 - Aug 16
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

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.
￥16,583
￥20,485 total
includes taxes & fees
Aug 30 - Aug 31
Ameristar Casino Hotel East Chicago
View all properties

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Shout to Lisa at the front desk. Lisa was awesome and should be promoted!"
Shane 4-night trip
Posted 16 hours ago
Blue Chip Casino Hotel and Spa
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

8/10 Good
"Ok for what we needed."
Whitley 1-night trip
Posted 18 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 22 hours ago
Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

8/10 Good
"Felt the property could have been very good. It has a super cool setting and rooms over the water was fun. However the room was not so good. It needs better cleaning protocols."
Randy 2-night trip
Posted 2 days ago
Waterbird Lakeside Inn
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 2 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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