Chesterton Vacations from $285

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$285
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$417
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
A bit surprised that there was no business facility room despite being listed as a hotel feature

Reviewed on Oct 9, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
Save 100% on your flight
$300
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight
$618
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$476
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
👍

Reviewed on Oct 8, 2026

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Stay near popular Chesterton attractions

A sandy beach with the ocean in the background and a grassy hill with trees.

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.
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A sandy beach with a large tree trunk in the foreground and a clear blue sky.
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.
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A pathway leading to a sign reading "Coffee Creek Watershed Preserve."

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.
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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.
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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.
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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.
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Portage Imagination Glen Park

Explore the great outdoors at Portage Imagination Glen Park, a lovely green space in Chesterton. Stroll along the beaches or visit the shops in the area.
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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.
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Chesterton Hotel Deals

Spring House Inn

Spring House Inn

303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
$103 nightly
$116 total
Nov 1 - Nov 2
Total with taxes and fees
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
$85 nightly
$95 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Loved the balcony looking out on the small lake behind the hotel. The front desk clerk was nice. Updated bathrooms were nice ecxept ours would not stay closed & had to use a washcoth to hold to closed.Otherwise a very nice stay for going to Indiana Dunes State Park"

Reviewed on Oct 8, 2026

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
$95 nightly
$106 total
Oct 26 - Oct 27
Total with taxes and fees
Waterbird Lakeside Inn
See all 1,422 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, offers a perfect blend of outdoor adventure and scenic beauty. Visitors can explore popular attractions like local parks, enjoy nature walks, and take advantage of biking trails. The recreational areas and playgrounds make it an ideal destination for families, while nature enthusiasts will appreciate the opportunity for little sightseeing and exploration of the area's natural landscapes.

Shopping

In Chesterton, you can shop at local boutiques and specialty stores. If you're up for a drive, visit Lighthouse Place Premium Outlets for a variety of shops, or explore Westfield Southlake Mall for more options and entertainment. Garwood Orchards offers unique gifts and local produce.

Recreation

Explore Marquette Park for a serene day surrounded by nature, perfect for relaxation and mindfulness. Experience the charm of Chicago Street Theatre for an evening filled with culture and entertainment. For outdoor enthusiasts, enjoy a round of disc golf at the nearby Disc Golf Course, embracing friendly competition.

Adventure

Experience thrills at Deep River Water Park, located 13 miles from Chesterton, where you can enjoy exciting water slides and family fun. For an adrenaline rush, visit Team Combat LIVE, 14 miles away, featuring immersive arcade battles. Don’t miss the scenic Cowles Bog Trailhead, perfect for hiking right in Chesterton.

Nightlife

Experience a unique nightlife in Chesterton with a visit to the Round Barn Union Pier Tasting Room, located 25 miles away. Enjoy a cozy pub atmosphere filled with entertainment and romantic vibes, perfect for unwinding after a day of exploration.

*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 fantastic destination for outdoor enthusiasts and families alike, offering beautiful scenery and adventure opportunities. Visitors can explore the stunning beaches and trails of the nearby Indiana Dunes National Park, as well as enjoy the local urban parks. With various attractions catering to outdoor activities and family experiences, Chesterton promises a memorable getaway for all types of travelers.

  • Indiana Dunes National Park: Just 3 miles from Chesterton, this national park offers breathtaking scenery and a variety of outdoor adventures. Explore miles of sandy beaches, hike scenic trails, and enjoy the diverse ecosystems that make this park a natural wonder.
  • Lake View Beach: Located 6 miles away, Lake View Beach is a serene spot perfect for relaxing under the sun. With its soft sands and stunning views of Lake Michigan, it’s an ideal place for swimming, picnicking, or simply soaking in the beach vibes.
  • Indiana Dunes Visitor Center: Situated within Chesterton, this visitor center is your gateway to adventure. Families can learn about the park's natural history and find resources for exploring the surrounding outdoor wonders, making it a great starting point for your trip.

Tips to save on your trip to Chesterton

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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

What's included in a Chesterton vacation package?
A Chesterton vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in Chesterton offer free breakfast, providing a convenient start to your day. For flights, you'll typically fly into Chicago O'Hare International Airport (ORD), about 50 miles from Chesterton, or other regional airports.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Chesterton vacation package?
When you bundle, you can save up to 30%*. To save money on a Chesterton package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Chesterton?
For families, a Chesterton vacation package built around a stay at Hilton Garden Inn Chesterton (rated 8.3 out of 10) is a strong choice. This hotel offers family rooms, an indoor pool, and a restaurant, with travelers often praising its spacious rooms and accommodating staff.Couples seeking a romantic getaway might prefer a package with Spring House Inn. Rated 8.1 out of 10, this inn features a bar/lounge and an indoor pool, and travelers frequently highlight its fantastic staff, cozy rooms, and beautiful location near Indiana Dunes National Park.If you're looking for the best value, consider a Chesterton vacation package that includes Quality Inn Chesterton near Indiana Dunes National Park I-94. This hotel provides free breakfast and rooms with kitchens, and travelers often note the great breakfast and convenient location.
What are the top things to do in Chesterton?
A Chesterton vacation offers plenty of outdoor and nature-focused activities, from exploring national parks to relaxing on Lake Michigan's shores:Browse and book things to do in Chesterton on Expedia.
Do you need to rent a car in Chesterton, or is public transport enough?
For a Chesterton vacation package, a rental car offers the most flexibility to explore the area's outdoor attractions and beaches. While Chesterton does have some public transport options, a car makes it easier to reach the various natural parks and lakeside spots.The Northwest Indiana Commuter Transportation District operates a regional train service, with a stop at the Dune Park station north of Chesterton, providing connections to Chicago and South Bend. Local bus routes also serve the area, including indirect connections to Valparaiso University on weekends. However, for exploring the many beaches and parks that make up a Chesterton beach vacation package, having your own vehicle is often recommended.
Are Chesterton vacation package hotels conveniently located?
Chesterton vacation package hotels are generally well-located for exploring the area's natural attractions. Many properties are situated close to central Chesterton and the Indiana Dunes National Park.For instance, Spring House Inn and Best Western Indian Oak are both about 1 mile from central Chesterton. The Hilton Garden Inn Chesterton is about 3 miles from central Chesterton. This proximity makes it easy to access the town's amenities and the nearby natural beauty.
Can I change or cancel my Chesterton vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chesterton vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chesterton vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesterton vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chesterton?
To find last-minute vacation packages to Chesterton, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chesterton vacation packages?
Free cancellation on a Chesterton vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chesterton vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesterton getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chesterton vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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.