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Chesterton Vacations from $602

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The Latest Chesterton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 20 - Aug 24

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.2/10 - Very Good (2,848 reviews)
    "Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay."
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $904
    $602
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Full-size fridge, microwave, oven, stovetop
    Sep 30 - Oct 5

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (502 reviews)
    "Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
    Reviewed July 14, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,517
    $918
    per traveler
    found 18 hours ago
    Level Chicago – Old Town
  • Lobby sitting area
    Aug 26 - Aug 30

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.4/10 - Very Good (2,041 reviews)
    "Clean room but the bathroom is the smallest one I've experienced in a hotel."
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,085
    $683
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Front of property
    Aug 20 - Aug 24

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,749 reviews)
    "The room and hotel exceeded my expectations. The hotel was located in the best spot. I would definitely stay here again."
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,323
    $849
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Smart TV
    Aug 20 - Aug 24

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (528 reviews)
    "Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!"
    Reviewed July 17, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,135
    $756
    per traveler
    found 1 day ago
    Level Chicago Fulton Market

Where to stay in Chesterton

Find the best Chesterton areas and neighborhoods for the activities you enjoy most. Learn more about Chesterton
Learn more about Chesterton
A sandy beach with a large tree trunk in the foreground and a clear blue sky.
Photo by Kapone Flores-Arellano
Open Photo by Kapone Flores-Arellano

Porter Beach

While visiting Porter Beach, you might make a stop by sights like Indiana Dunes National Park and Lake Michigan.

Discover the most popular places to visit in Chesterton

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.

Chesterton Hotel Deals

Property entrance

Spring House Inn

Spring House Inn
2.5 star property
1.3 mi from Chesterton
9.0 out of 10, Wonderful, (1,003 reviews)
"Beautiful and clean hidden gem!! My daughter thinks it a hotel Lorelei Gilmore would run!! Easy access to Indiana Dunes and Chesterton. Repeat guest!"
$143 nightly
The price is $161
Jul 20 - Jul 21
Total with taxes and fees
Spring House 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.
See all properties in Chesterton

Frequently Asked Questions

How much does a Chesterton vacation package cost?

You can grab a vacation package to this top destination from $602 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.

Book with confidence

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.

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.

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