Best-rated hotels in Chesterton for your unforgettable stay

Detailed descriptions, travelers’ reviews, and handpicked hotel collections will help you book your perfect accommodation.

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Why book with us?

Choose from exclusive hotel collection

We offer thousands of Chesterton hotels and accommodations from world's renowned hotel chains to unique gems of the region you won’t find anywhere else.

Enjoy seamless booking experience

Once you choose your best place to stay, take a minute to complete a quick reservation form and get an instant confirmation letter to your email address.

Benefit from flexible travel options

We provide the most flexible cancellation options, so you get your deposit back in case of a change of plans or other unforeseen circumstances.

Find a hotel

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

Hotels by location

Nearby
City Center Chesterton 12
Richardson Wildlife Sanctuary Chesterton 1
National Park Svc 8
Chesterton Park 12
Dunes State Park 7
Dogwood Park 12
Chesterton Town Park Board 12
Victory Park 12
Burns Harbor Town Park Dept 12
Landmarks
Parks
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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 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 your trip arrangements by booking one of our hand-picked hotels

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

558 Indian Boundary Road, Chesterton, United States

Good
272 reviews

78 US$

min. price/night

Hilton Garden Inn Chesterton

501 Gateway Boulevard, Chesterton, United States

Excellent
188 reviews

110 US$

min. price/night

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

556 Indian Boundary Road, Chesterton, United States

Good
390 reviews

70 US$

min. price/night

Quality Inn Chesterton Near Indiana Dunes National Park I-94

418 Council Road, Chesterton, United States

Good
212 reviews

76 US$

min. price/night

Fairbridge Inn Express Chesterton

713 Plaza Drive, Chesterton, United States

Good
16 reviews

90 US$

min. price/night

Travelers’ choice

Check out the most booked accommodations to find reliable places that our users have tried and tested.
Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms

105 West Michigan Avenue, Chesterton, United States

Excellent
28 reviews

Your Midwest Dunes Vacation Tri-State Paradise!

1541 Eagle Street, Chesterton, United States

Excellent
9 reviews

228 US$

min. price/night

Cozy Abode About 3 Mi To Indiana Dunes Natl Park

803 S Calumet Rd, Chesterton, United States

Excellent
4 reviews

Riley'S Railhouse Bed & Breakfast

123 North 4Th Street, Chesterton, United States

176 US$

min. price/night

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