Chesterton Holidays from £956

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Your Chesterton Holiday

With every last detail organised before you go, our Chesterton holiday packages mean you can simply focus on letting the good times roll. Whether you're staying in the neighbourhood of Miller Beach, which is great for nature, or someplace else in town, this fun city offers a wealth of discoveries. Eager to start exploring your surroundings? Indiana Dunes National Park, Indiana Dunes State Park and Dune Acres Beach are among the top-rated places to visit during a trip to Chesterton. Don't delay visiting this destination any longer. Your ultimate Chesterton holiday is a couple of clicks away with Expedia.

The Latest Chesterton Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (205 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,896 reviews)
Nice hotel close to shopping and restaurants. Hotel restaurant breakfast buffet food was cold. Valet parking too expensive. Staff was nice and accommodating. Our floor was noisy with people partying on Friday night.

Reviewed on 8 May 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
per person
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,197 reviews)
Good service and cleaning , the hotel is close to all principal areas of the city.

Reviewed on 10 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago

Reviewed on 10 May 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The staff were very kind when we requested to extend our stay -they made sure we got the best value as well. The rooms are small but well maintained. Perfect for a small weekend trip!

Reviewed on 10 May 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,124 reviews)
Need more pillows in the room.

Reviewed on 10 May 2024

Chesterton Essential Information

Language
English
Currency
U.S dollars
Population
13,400
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach

Our pick of the best Chesterton Hotel Deals

Waterbird Lakeside Inn
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the clean rooms in their reviews.
7.8/10 Good! (696 reviews)
"The property was older but nice. It was older and parts of it were not very clean. However it is conveniently located to lots of dining etc"

Reviewed on 6 May 2024

Waterbird Lakeside Inn
Best Western Indian Oak
Best Western Indian Oak
2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the pool in their reviews. ...
8.4/10 Very Good! (971 reviews)
"Best hotel ive stayed at in a while. Normal breakfast options. Pool is huge and not freezing. They also had a sauna. Overall dont have anything to complain about."

Reviewed on 28 Apr 2024

Best Western Indian Oak
Spring House Inn
Spring House Inn
2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (880 reviews)
"Quiet and peaceful inn. A nice and clean room was good, butit was a bit of a problem that the soundproofing was not good."

Reviewed on 5 May 2024

Spring House Inn
See all 1,260 properties in Chesterton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Chesterton holiday with Expedia?
Choose Expedia to plan your next big adventure simply and all in the same place. Our top tip for scoring a terrific deal on a Chesterton retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a few awesome tours and activities. Most bookings also come with flexible cancellation policies, so there’s no need to panic if you have to change plans. Round-the-clock help with amending and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Chesterton?
Chesterton can get busy in May, June and July, so if you want to avoid the crowds, travel in December, January and February. Arrange your visit to Chesterton based on what type of adventure you’re looking for. January is the coolest month, when average daytime temperatures are -3ºC. In July, the warmest period, expect temperatures of around 22ºC during the day.
What are the top hotels for my holiday in Chesterton?
Best Western Indian Oak in the Porter Beach neighbourhood is a wonderful choice for a Chesterton holiday. Reserve a room here and you’ll be well-placed to explore all that this vibrant city has to offer.
How do I get a cheap holiday to Chesterton?
If you love bargains, combine your bookings into a Chesterton holiday. Whether you’re looking for hotels, flights, hire cars or day tours, you can book them all in one place. You’ll have a wealth of choice at your fingertips as well. Expedia has over 400 airlines and 321,000 hotels around the globe to pick from. Fly with who you want, stay in a place you like and save precious money — now that’s the ideal holiday! Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Chesterton holiday?
Offering top attractions such as Indiana Dunes National Park and Indiana Dunes State Park, a holiday in Chesterton is full of fun things to do and see. Lake View Beach and Portage Lakefront Beach are a couple of other sights also worth a look.
What is the best area to stay in when on holiday in Chesterton?
If you plan to check out Coffee Creek Watershed Conservancy Preserve, maximise your time sightseeing and stay nearby. It’s one of the best attractions in Chesterton.
Do I need a visa for my Chesterton holiday?
Check the latest information on official government websites. Your nationality and whether you’re visiting for business, leisure or study will determine if you require a visa for Chesterton. Get familiar with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow plenty of time for processing. Some visas may take weeks or even months to obtain, depending on the country.
What should I wear on my Chesterton holiday?
Consider the type of activities planned during your trip to Chesterton and take versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, look up a few style blogs or relevant social media accounts. Pack with confidence by looking up the local weather conditions in Chesterton. July brings the warmest temperatures, with daytime averages of 22ºC, while January days average -3ºC, making it the coolest time of year.
What does an Expedia Chesterton holiday include?
Flights, hire cars and hotels — we’ve got them covered. With Expedia, you can create your Chesterton travel package the way you want. All you have to do is work out exactly what you need. Once you’ve made your booking, why not add fun things like activities and experiences? The more you bundle, the bigger your savings! Explore a large selection of property types and select one that matches your travel needs. The most sought-after rentals here are private holiday homes and cottages. With Expedia, you can easily customise your Chesterton escape any way you want.
Does Expedia offer Book Now, Pay Later Chesterton holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Don’t forget to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying in multiple transactions works for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • No-deposit holidays: When you come across an incredible deal but don’t have the full amount yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Chesterton Expedia holiday?
Yes, you sure can. Expedia has access to more than 400 partner airlines globally, so choose the carrier that best suits your budget and travel needs.

Discover the most popular places to visit in Chesterton

Image for Indiana Dunes State Park

Indiana Dunes State Park

4/5(1 review)

The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

Indiana Dunes State Park
Image for Bailly Homestead - American Indians and Fur Traders

Bailly Homestead - American Indians and Fur Traders

You can find out about the history of Porter with a trip to Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.

Bailly Homestead - American Indians and Fur Traders
Image for Waverly Beach

Waverly Beach

Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.

Waverly Beach

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.