Chesterton Holidays
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Top Flight + Hotel Deals in Chesterton
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
€1,391
per person
2 Oct - 8 Oct
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on 12 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
€1,995
per person
8 Oct - 14 Oct
found 15 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
It was a good stay. Views, room cleaning everyday and convenient, but you will spend a lot going back and forth to the magnificent mile. No pool but has a Ferris wheel . I recommend.
Reviewed on 17 Aug 2026
Top hotels in Chesterton
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
€107
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Clean room"
Reviewed on 16 Aug 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
€109
18 Aug - 19 Aug
includes taxes & fees
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
€120
1 Sept - 2 Sept
includes taxes & fees
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
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.
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.
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from €1,391 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.
