The Best Luxury Hotels in Chesterton, IN from ￥13,537 in 2026

A wooden staircase ascending a sandy hill with sparse vegetation.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Chesterton Luxury Hotels

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chesterton luxury hotels

A modern lobby with a sofa, coffee table, and a fireplace.

A multi-story hotel with a prominent 'AMERISTAR' sign, featuring a modern architectural design with large windows and a flat roof.

A bar area with a counter, multiple TVs, and a seating area with chairs and tables.

A casino floor with multiple slot machines and a few blackjack tables.

1. Ameristar Casino Hotel East Chicago

East Chicago

Art Deco elegance meets beachfront luxury with casino thrills, fine dining, and marina views.

￥18,785

￥22,937 total

includes taxes & fees

Oct 6 - Oct 7

View all properties

Top Chesterton Hotel Reviews

Quality Inn Chesterton near Indiana Dunes National Park I-94

8/10 Good

"Hotel was great! Just wish there was an elevator. But the front desk gal helped me up the stairs with my stroller - she was fabulous!"

Ameristar Casino Hotel East Chicago

10/10 Excellent

"Staff went above and beyond to accommodate me and my friends"

Waterbird Lakeside Inn

10/10 Excellent

"I arrived at the hotel after being discharged from a local hospital. I was traveling from NY to Colorado by motorcycle when I was hit by a truck. After 2 days in the hospital, I booked this hotel to recover, treat my wounds and wait for my motorcycle to be inspected. I ended up staying at Waterbird for 6 nights. The staff was amazing. So kind, caring and helpful. My room was quite large, comfortable and clean. The private lakeside deck was the perfect spot to drink morning coffee and relax while my wounds started to heal. Thank you so much, Missy and Max at the front desk. Thank you to Christina, Jessica, and Tracy, the housekeepers who made sure I had what I needed each day. I am truly grateful."

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, Indiana Dunes Visitor Center, and Bailly Homestead - American Indians and Fur Traders. If you have extra time while you're in the area, you might want to see Indiana Dunes National Park and Indiana Dunes State Park.

Explore a world of travel with Expedia

More ways to book

Book Luxury Hotels in Chesterton on Expedia.com

Find Luxury Hotels in Chesterton, IN

Change your mind

Treat yourself

Be picky