Best-rated Hotels in Chesterton for an Unforgettable Stay

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Choose from exclusive hotel collections.

We offer thousands of Chesterton hotels and accommodations from some of the world's most renowned hotel chains as well as unique gems in the region that you won’t find anywhere else.

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Hotels by class
3 stars 2
2 stars 3
Unrated 9
Accommodation type
Holiday homes 6
Inns 3
Hotels 2
Apartment 1
Bed & Breakfast 1
Motel 1
Thematic Hotels
Luxury accommodations 8
Extended Stay 7
Vacation Rentals 7
Family Friendly hotels 7
Pet-friendly hotels 5
Private Villas 5
Cheap and budget hotels 3
Hotels with indoor pool 2
Jacuzzi 2
Beach hotels 2
Resorts 2
Business hotels 2
Romantic hotels 2
Golf hotels 1
Exceptional design hotels 1
Central hotels 1
Boutique hotels 1
Sustainability certification 1
All Chesterton hotels

Hotels by location

Nearby
City Centre Chesterton 11
Burns Harbor Town Park Dept 11
Chesterton Town Park Board 10
Dunes State Park 7
National Park Svc 7
Richardson Wildlife Sanctuary Chesterton 1
Victory Park 10
Dogwood Park 10
Landmarks
Park
Landmark
Popular attractions
Chicago Metropolitan Area >
Chesterton

Welcome To Chesterton

Discover the hidden gem of Chesterton, where small-town charm meets natural beauty. Stroll along the picturesque streets lined with historic houses, indulge in local cuisine at quaint cafes, and immerse yourself in the vibrant arts scene. Experience the enchanting landscapes, from the sandy shores of Lake Michigan to the scenic trails through Indiana Dunes State Park. Plan your visit to Chesterton today and uncover a world of captivating attractions and endless adventure.

What Our Users Say About Popular Chesterton Hotels

Warwick Allerton Chicago
9.8

Exceptional

us Ethel 07 September 2022
Fancy brand-new hotel in the middle of Chicago.
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Central Loop Hotel
9.8

Exceptional

us Ann 07 October 2022
Spotless, recently refurbished hotel, it has perfect staff and location. It is set in a central area, walking distance to a church and an art gallery.
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Eurostars Magnificent Mile
9.8

Exceptional

us Susan 14 July 2022
I liked this trendy boutique hotel and stayed for 2 nights here. I've booked king room with fantastic views and everything was perfect.
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Embassy Suites By Hilton Chicago Downtown Magnificent Mile
9.8

Exceptional

us William 14 November 2022
It was the best of Chicago hotels I visited before now. For a 4 star hotel everything was amazing, I appreciated to be here. The staff were attentive and accommodating. The location was stunning, a 10-15 minute walking distance from Chicago Water Tower.
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River Hotel
9.8

Exceptional

us Craig 13 December 2022
Enjoyed staying here. the staff were great and the location was convenient. Loads of dining options and bars nearby to grab a bite to eat or have a drink 🍹.
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Raffaello Chicago
9.8

Exceptional

us Liz 14 August 2022
The hotel was fairly clean. the location was stunning near Michigan Avenue with easy access to most shops. - I liked the updated and cozy room with a nice view. - the staff were accommodating and exceptional in every interaction we had.
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Hotel Saint Clair - Magnificent Mile
9.8

Exceptional

us Joshua 23 December 2022
The hotel is clean and budget-friendly. Located conveniently close to restaurants. The rooms are newly decorated and functional. Friendly and helpful staff at the reception desk.
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Freehand Chicago
9.8

Exceptional

us Curtis 15 February 2023
Clean rooms with air conditioning and a private bathroom, plus free WiFi 🌟.
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Hotel Felix
9.8

Exceptional

us Harry 23 August 2021
We loved this interesting place and its unbeatable location. The room we had was contemporary where toilet did n't flush. It had superb rooftop restaurant.
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Hyatt Regency Chicago
9.8

Exceptional

us Ralph 02 November 2022
I had a great time during my 2-night stay here, the location was perfect, just a short walk to Riverwalk, and the breakfast options were fantastic.
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Save Time on Trip Arrangements by Booking One of Our Hand-picked Hotels

Exclusive 3-star Hotels
Quality 2-star Hotels
Enjoy authentic experiences without compromising on comfort and convenience.
Best Western Indian Oak

558 Indian Boundary Road, Chesterton, United States

Good
284 reviews

79 US$

min. price/night

Hilton Garden Inn Chesterton

501 Gateway Boulevard, Chesterton, United States

Excellent
202 reviews

110 US$

min. price/night

Discover the hidden gems of Chesterton by booking one of its 2-star hotels.
Waterbird Lakeside Inn

556 Indian Boundary Road, Chesterton, United States

Good
408 reviews

70 US$

min. price/night

Quality Inn Chesterton Near Indiana Dunes National Park I-94

418 Council Road, Chesterton, United States

Good
209 reviews

76 US$

min. price/night

Fairbridge Inn Express Chesterton

713 Plaza Drive, Chesterton, United States

Good
17 reviews

90 US$

min. price/night

Travelers’ Choice

Check out our most booked accommodations and find reliable places that users have tried and tested.
Blue Birdhouse - Indiana Dunes - Pet Friendly

5 West Beam Street, Chesterton, United States

Excellent
27 reviews

165 US$

min. price/night

Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms

105 West Michigan Avenue, Chesterton, United States

Excellent
26 reviews

Furness Mansion Hotel

1491 N Furnleigh Ln, Chesterton, United States

Good
10 reviews

Your Midwest Dunes Vacation Tri-State Paradise!

1541 Eagle Street, Chesterton, United States

Excellent
9 reviews

212 US$

min. price/night

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