Chesterton Vacations from $342

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $566, price is now $342 per person
$342
per person
Mar 4 - Mar 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great view, awesome bar, fun staff.

Reviewed on Dec 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $743, price is now $431 per person
$431
per person
Mar 4 - Mar 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $376 per person
$376
per person
Mar 4 - Mar 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Excellent, close to everything

Reviewed on Dec 26, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $765, price is now $450 per person
$450
per person
Mar 4 - Mar 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Room was really clean and fresh

Reviewed on Dec 27, 2025

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $575, price is now $348 per person
$348
per person
Jan 26 - Feb 2
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
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Discover the most popular places to visit in Chesterton

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

Indiana Dunes State Park

4.5/5(185 reviews)

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
This is a very nice place to hike.

Bailly Homestead - American Indians and Fur Traders

4.5/5(3 reviews)

You can find out about the history of Porter with a stop at Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.

Bailly Homestead - American Indians and Fur Traders

Indiana Dunes Visitor Center

Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area.

Indiana Dunes Visitor Center

Chesterton Hotel Deals

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 out of 5
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $105 total per night from Dec 30 to Dec 31
$105 total
Dec 30 - Dec 31
Total with taxes and fees
8/10 Very Good! (999 reviews)
Great staff and hospitality! Everything was clean and tidy.

Reviewed on Nov 28, 2025

Comfort Inn & Suites Porter near Indiana Dunes
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Jan 11 to Jan 12
$123 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Very clean room Staff friendly

Reviewed on Dec 7, 2025

Hilton Garden Inn Chesterton
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
$93 nightly
The price is $105 total per night from Jan 2 to Jan 3
$105 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
We we went to breakfast and the juice was out as well as the yogurt. Went to front desk, told them, and she immediately went and changed them out. Front desk was super friendly and even allowed us to swim longer than pool was open. Pillows are like the size of throw pillows lol which was odd but ...

Reviewed on Dec 23, 2025

Best Western Indian Oak
See all 1,387 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.

Find the Best Chesterton Vacation Packages

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.

Chesterton Essential Information

Language
English
Currency
U.S dollars
Population
13,400
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach

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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 $342 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.

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