Chesterton Holidays
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Chesterton Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
S$1,578
per person
8 Nov - 12 Nov
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Had to request towels three times throughout the day before brought up. Thermostat stopped working, maintenance came and “fixed”, it stopped again in the middle of night spent a stuffy, hot night’s sleep. Shower drain clogged, informed front desk, maintenance never came that day. Glad we checked out the next day before anything else went wrong.
Spend your $ somewhere else!
Reviewed on 18 Sept, 2026
Top hotels in Chesterton
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
S$123
1 Oct - 2 Oct
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"The priority had an Forest charm and everything was well cared for except the pool which had sand in it and lots of chlorine. Enjoyed our stay and would come again."
Reviewed on 17 Sept, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
S$158
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Pool, sauna, view, all excellent! What a pretty place!"
Reviewed on 18 Sept, 2026
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Fully refundable
S$149
18 Oct - 19 Oct
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Pleasant staff very clean room"
Reviewed on 14 Sept, 2026
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.
Stay near popular Chesterton attractions
Photo by Susan Ross
Indiana Dunes State Park
9.0/10 (717 reviews)
Towering sand dunes rise nearly 200 feet above Lake Michigan's pristine shoreline. Hike the 16.5 miles of trails through diverse ecosystems or relax on the beach with panoramic lake views.
Coffee Creek Watershed Conservancy Preserve
8.6/10 (25 reviews)
Explore 157 acres of diverse Indiana ecosystems along five miles of scenic trails at Coffee Creek Watershed Preserve. Watch for migrating salmon and trout from one of seven bridges spanning the tranquil creek.
Photo by Kapone Flores-Arellano
Waverly Beach
9.0/10 (20 reviews)
Waverly Beach offers serene shoreline views and sandy beaches along Lake Michigan within Indiana Dunes State Park. Follow the easy 0.9-mile trail through shaded woods to reach this peaceful swimming and sunbathing haven.
Bailly Homestead - American Indians and Fur Traders
9.0/10 (27 reviews)
Step into Joseph Bailly's 1820s fur trading post, a cultural crossroads of early frontier life. Explore the restored main house, chapel, and log buildings while walking scenic trails through Indiana's rich history.
Lustron House
8.0/10 (9 reviews)
This rare Lustron House showcases innovative post-WWII architecture with its porcelain-enameled steel panels—a perfect example of mid-century prefabricated housing design for architecture enthusiasts.
Dune Acres Beach
10.0/10 (2 reviews)
This serene Lake Michigan shoreline offers a peaceful retreat amid natural dunes and scenic beauty. Enjoy soft sands and gentle waves while exploring nearby trails perfect for birdwatching and connecting with nature.
Chellberg Farm
8.8/10 (29 reviews)
This historic Swedish-American farmstead showcases 19th-century rural life with its 1885 brick house and original barn. Visit during Maple Sugar Time in March for traditional syrup-making demonstrations.
Chesterton Art Center
You can spend time browsing the exhibits at Chesterton Art Center during your trip to Chesterton. Stroll along the beaches or visit the shops in the area.
Frequently asked questions
How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from S$1,578 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?
- 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.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
