Chesterton Holidays from NZ$1,675

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The Latest Chesterton Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 13 hours ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
8.2/10 Very Good! (1,766 reviews)
Property was nice and clean today

Reviewed on 25 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 6 hours ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
Outstanding breakfast!

Reviewed on 23 Jun. 2025

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 13 hours ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
Great location. Nice rooms

Reviewed on 22 Jun. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 13 hours ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (3,355 reviews)
I have stayed in many Chicago hotels. This hotel is in the city center and walkable to everything you want to see. It is modern and clean. The rooftop bar is very popular. So popular we couldn't get a seat. The restaurant below the rooftop is less busy. The food is very good. Our room was modern and clean and tiny. The bed was comfortable and the bathroom modern with nice products. My lower star ranking is that for the price tag I prefer the Thompson or Four Seasons or JW Marriott or the Langham. This hotel might appeal more to a younger crowd. I wouldn't stay here again with so many very nice hotels nearby.

Reviewed on 24 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
28 July - 2 Aug
found 13 hours ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun. 2025

Chesterton Holiday

Our pick of the best Chesterton Hotel Deals

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 NZ$261 per night from 29 June to 30 June
NZ$261
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"location"

Reviewed on 24 Jun. 2025

Best Western Indian Oak
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 NZ$222 per night from 26 June to 27 June
NZ$222
26 June - 27 June
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"The staff was friendly and the grounds are wonderful"

Reviewed on 24 Jun. 2025

Spring House Inn
Waterbird Lakeside Inn
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 29 June to 30 June
NZ$202
29 June - 30 June
includes taxes & fees
8/10 Very Good! (846 reviews)
"We were locked out at 8:30 AM (key card not working) and no one was available at the desk to help. Card finally worked after ~20 attempts. Everything else was fine."

Reviewed on 22 Jun. 2025

Waterbird Lakeside Inn
See all 1,352 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.

Frequently asked questions

How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from NZ$1,675 on Expedia. However, how much your holiday to Chesterton costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Chesterton?
If you're looking to book a cheap Chesterton holiday package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and flights during these months --- perfect for a budget-friendly getaway.
How many days is enough for Chesterton?
Typically, a few days is enough for a Chesterton holiday. With a carefully crafted itinerary, you can see all the top attractions like Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton holiday guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good holiday destination.
How to find the best Chesterton package deals?
Landing a cheap Chesterton package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Chesterton package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalise your Chesterton trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chesterton?
If you're considering an impromptu Chesterton holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterton?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Chesterton.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Chesterton. Then, pick a property that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Chesterton. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Chesterton holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.