Chesterton Holidays from £1,263

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    Packages with flights are ATOL protected

Your Chesterton Holiday

When you organise a holiday package to Chesterton, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this lively city from your base in a neighbourhood like Miller Beach, which is great for nature. If your trip to Chesterton includes a little sightseeing, check out well-known attractions like Indiana Dunes State Park, Coffee Creek Watershed Conservancy Preserve and Portage Lakefront Beach. Whatever your travel plans or the size of your budget, organising your ultimate tailored Chesterton holiday is easy with Expedia.

Top Chesterton Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
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
9 Oct - 14 Oct
found 5 hours ago
Return flight included
Aberdeen (ABZ) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
It’s super convenient bc it’s on the pier but beware it’s connected so it’s not its own building. Still we felt safe and it was very clean

Reviewed on 16 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Aug - 30 Aug
found 20 hours ago
Return direct flight included
Aberdeen (ABZ) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on 15 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 5 hours ago
Return flight included
Aberdeen (ABZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 5 hours ago
Return flight included
Aberdeen (ABZ) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on 17 Jul 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
per person
9 Oct - 14 Oct
found 5 hours ago
Return flight included
Aberdeen (ABZ) to Chicago (ORD)
8.8/10 Excellent! (3,033 reviews)
I had an excellent experience during my stay. The service was outstanding—staff were friendly, attentive, and went out of their way to ensure everything was perfect. The location was also ideal, offering convenient access to everything I needed in the city. If I find myself back in Chicago, this will definitely be my first choice for accommodations. Highly recommended.

Reviewed on 16 Jul 2025

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

Top hotels in Chesterton

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is £108 per night from 3 Aug to 4 Aug
£108
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The surroundings were beautiful and quiet. Liked how kitchy the building"

Reviewed on 11 Jul 2025

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is £92 per night from 13 Aug to 14 Aug
£92
13 Aug - 14 Aug
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
Nice and convenient hotel
"Nice hotel that is super convenient to the Indiana dunes. Pool was nice and the service was friendly and helpful."

Reviewed on 14 Jul 2025

Best Western Indian Oak
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is £104 per night from 17 Aug to 18 Aug
£104
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"We loved staying here."

Reviewed on 26 Jun 2025

Hilton Garden Inn Chesterton
See all 1,377 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.

* 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.