Chesterton Vacations from $156

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Your Chesterton Vacation

When you organize a vacation 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 neighborhood 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, organizing your ultimate tailored Chesterton vacation is easy with Expedia.

The Latest Chesterton vacation packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
The Langham, Chicago
Hyatt Regency Deerfield
The Stella Hotel & Ballroom
Hotel Riu Plaza Chicago
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Discover the most popular places to visit in Chesterton

Chesterton Hotel Deals

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
$113 nightly
The price is $127 total per night from Sep 2 to Sep 3
$127 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Charm"

Reviewed on Aug 22, 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
$102 nightly
The price is $114 total per night from Sep 1 to Sep 2
$114 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"Very lovely place to stay. The lake is very pretty with lots of wildlife. Although the hotel is older, it is very quaint. It is also very quiet, the staff were very pleasant and helpful, and the room and bathroom were so very nice. I’d definitely stay here again."

Reviewed on Aug 18, 2025

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Aug 26 to Aug 27
$115 total
Aug 26 - Aug 27
Total with taxes and fees
8/10 Very Good! (910 reviews)
Good stopping place.
"We checked in and found the room to be nice for the cost. The only downside is that it is above a lake and the humidity in Indiana at this time of year is high so the room was humid. The A/C worked fine and cooled the room, but the level of humidity was higher then I preferred. There was no musty ..."

Reviewed on Aug 22, 2025

Waterbird Lakeside Inn
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.

Things to do in and around Chesterton

Chesterton, Indiana, is perfect for those seeking outdoor adventures and scenic beauty. Enjoy various recreational areas, playgrounds, and fairgrounds. Popular activities include exploring nature through biking trails, engaging in nature walks, and taking in some light sightseeing. Whether you're looking for family-friendly fun or a peaceful retreat in nature, Chesterton offers a delightful mix of attractions for every visitor.

Shopping

In Chesterton, you can visit local shops for unique gifts. If you're up for a drive, Lighthouse Place Premium Outlets (11 miles away) and Westfield Southlake Mall (16 miles away) offer diverse shopping experiences with entertainment and dining options. Garwood Orchards (13 miles away) is great for local produce and gifts.

Recreation

Experience tranquility at Marquette Park, where you can unwind amidst nature. Enjoy a captivating show at Chicago Street Theatre, perfect for a date night or family outing. For some outdoor fun, head to the Disk Golf Course, where you can engage in a friendly game surrounded by fresh air.

Adventure

Experience splashes of fun at Deep River Water Park, located 13 miles from Chesterton, featuring thrilling slides and family attractions. For indoor excitement, visit Team Combat LIVE, 14 miles away, for arcade-style adventures. Explore the scenic Cowles Bog Trailhead right in Chesterton for an unforgettable hiking experience.

Nightlife

Chesterton's nightlife is vibrant and inviting. Visit the Round Barn Union Pier Tasting Room, about 25 miles away, for a cozy pub atmosphere filled with entertainment and romantic vibes. Enjoy a variety of drinks while soaking in the lively ambiance, perfect for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chesterton

Chesterton, Indiana, is a charming destination perfect for outdoor and adventure vacations. Visitors can enjoy beautiful beaches and explore the scenic landscapes of nearby state and urban parks. With a focus on family-friendly experiences, Chesterton offers a variety of attractions, including the renowned Indiana Dunes, making it an ideal spot for those seeking both relaxation and adventure in nature.

  • Indiana Dunes National Park: Located 3 miles from Chesterton, this stunning national park offers breathtaking scenery and outdoor adventures. Hike along scenic trails, explore diverse ecosystems, and enjoy the picturesque views of Lake Michigan.
  • Lake View Beach: Just 6 miles away, Lake View Beach provides a relaxing atmosphere with its sandy shores and gentle waves. It's a perfect spot for sunbathing, swimming, and enjoying beach vibes with family and friends.
  • Indiana Dunes Visitor Center: Situated within Chesterton, this visitor center is your gateway to adventure. With engaging exhibits and helpful staff, it’s ideal for families looking to learn about the park’s natural beauty and plan their outdoor activities.

Tips to save on your trip to Chesterton

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chesterton.
  • Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Chesterton.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this top destination from $156 on Expedia. However, how much your vacation 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?
You're likely to find lower rates and better availability in December, January and February. Check out our cheap Chesterton vacation packages and you could land some great off-season discounts.
How many days is enough for Chesterton?
Generally, a few days is ideal for a Chesterton vacation. With a well-organized schedule, you can visit all the popular sights including Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Chesterton?
Chesterton is a good vacation destination with attractions like Indiana Dunes Visitor Center among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Chesterton vacation promises a good time for everyone.
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," "Traveler 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalize 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 vacation package to Chesterton?
If you're considering an impromptu Chesterton vacation, 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.
Does Expedia offer Book Now, Pay Later Chesterton vacation packages?
Your Chesterton trip is meant to be an escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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