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Chesterton Vacations

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
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Ages of children at time of trip (for pricing, discounts)

Your Chesterton vacation

From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Chesterton vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.

Create your own Chesterton travel plans
Build your own Chesterton vacation itinerary. Choose a flight that matches your schedule and a hotel with the amenities you need. Book them together for extra discounts you won't find when booking separately.

Find Chesterton travel discounts
Be the first to know about exclusive offers and last-minute deals on Chesterton travel. Sign for our deals e-mail , or follow us on Twitter and Facebook for promo codes, discounts and more. Our global network of travel experts find big-time savings and travel deals just for you.

Get Chesterton travel support 24/7
Reach out to an Orbitz travel specialist for Chesterton vacation assistance. Our specialists are available around the clock at 1-800-504-3248. We can even help with last-minute Chesterton vacations.

Sign up for free Chesterton travel alerts
Make travel plans smoother with Orbitz Care Alerts. Receive real-time info about flight delays, weather and other events via phone, e-mail or text. Keep up to six other people in the loop with travel alerts, too.

Scope out your Chesterton vacation options and savings
With the Orbitz Matrix Display, you can view all your flight and hotel options quickly. Plus, you'll see what you can save on your travel packages when you book them together.

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Chesterton Vacation Packages

Hotel only $67


3 stars
3.8 / 5 36 reviews

558 Indian Boundary Road Map

Save 10% on your stay

Discover all that northern Indiana has to offer, from Indiana Dunes State Park to an easy commute to Chicago, from this charming Chesterton hotel. Conveniently located off the I-94 and the Toll Road, the BEST WESTERN Indian Oak makes it easy to experience the areas most... More

Hotel only $102

2 Hilton Garden Inn Chesterton

3 stars
4.0 / 5 11 reviews

501 Gateway Boulevard Map

Complimentary wired and Wi-Fi Internet Access

The Hilton Garden Inn Chesterton hotel in Indiana is conveniently located off Interstate 80-90 exit 31, with easy access to Valparaiso, Portage, Michigan City, Westville, South Bend and Gary, IN. Antique shopping is located nearby.All of our 120 guest rooms and suites at... More

Hotel only $59

3 Econo Lodge Chesterton

2 stars
2.0 / 5 1 reviews

713 Plaza Dr. Map

Conveniently located with easy access to I-94 and Indiana Toll Road I-80-90. Blue Chip and Empress Casino, Indiana Dunes and State Park, Pine Ski Resort and Chesterton Antique Market nearby. Several restaurants within walking distance. Amenities include free continental... More

Hotel only $69

4 Quality Inn Chesterton

2 stars
2.5 / 5 2 reviews

418 Council Road Map

The Quality Inn is conveniently located within walking distance to restaurants, shopping and the hospital and just a short drive to National Lakeshore, Dunes State Park, Bue Chip Casino, Four Winds Casino, Marquette Mall and Lighthouse Outlet Mall. This is a non-smoking... More