Chesterton Packages (Flight + Hotel)

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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 ฿3,307 per night from 21 Apr to 22 Apr
฿3,307
฿3,704 total
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (1,005 reviews)
"Keep up the good work and thank you for getting rid of the guests that were being rowdy"

Reviewed on 17 Apr 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 ฿2,839 per night from 27 Apr to 28 Apr
฿2,839
฿3,180 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,004 reviews)
"Quiet and safe and clean but no elevator"

Reviewed on 16 Apr 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 ฿3,664 per night from 5 May to 6 May
฿3,664
฿4,103 total
includes taxes & fees
5 May - 6 May
8.6/10 Excellent! (1,000 reviews)
"Hotel was really nice and clean overall, just a few small things, our vent fan in the bathroom didn't work and the TV was finicky to turn on."

Reviewed on 12 Apr 2025

Hilton Garden Inn Chesterton
See all 1,321 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 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.

Popular places to visit

Indiana Dunes State Park showing general coastal views and a sandy beach as well as a family

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