Chesterton Vacations

Hotel options

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

Room 1
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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.

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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.

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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.

Chesterton Vacation Packages

Hotel only $108

1 Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1199 reviews

520 South Michigan Ave Map

Winter Sale - Save 20%

With its neon-red sign standing out against the Chicago skyline, its vaulted Italianate ceilings, and glimmering 'Gold Room' banquet hall, the Congress Plaza Hotel makes an imposing first impression. Once known as the "Home of Presidents" due to its popularity with both... More

Hotel only $59

2 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 $71


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 $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

Hotel only $102

5 Hilton Garden Inn Chesterton

3 stars
3.8 / 5 12 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 $69

6 Springhouse Inn

3 stars
3.3 / 5 71 reviews

303 N. Mineral Springs Road Map

One of Chesterton's best hotels and inns, the Springhouse Inn hotel near Chesterton, Indiana provides lodging accommodations and meeting retreat option in Northwest Indiana near the Indiana Dunes State Park, the historic Bailly Homestead, Chellberg Farm and within minutes... More

Hotel only $69

7 Microtel Inn & Suites by Wyndham Michigan City

2 stars
3.9 / 5 41 reviews

9834 W 400 N Map

Stay 3, Save 20%

Enjoy modern comfort at affordable rates at this Microtel Inn and Suites by Wyndham Michigan City hotel conveniently located off Interstate 94 just five miles from Washington Park Zoo, and near restaurants, gaming and live entertainment at Blue Chip Casino, and outdoor... More

Hotel only $52

8 Red Roof Inn Michigan City

2 stars
2.5 / 5 34 reviews

110 West Kieffer Rd Map

This Red Roof Inn is Non Smoking. For shopping, gaming, or just enjoying the beautiful beaches, come to Michigan City. Lighthouse Place Outlet Mall, Blue Chip Casino, and Washington Park Beach are all within 5 miles of this hotel, while unique Indiana State Dunes are just... More

Hotel only $75

9 Country Inn & Suites By Carlson, Michigan City, IN

2 stars
3.8 / 5 21 reviews

3805 North Frontage Road Map

Save 20% on your stay

Complimentary High Speed Internet Access, Complimentary Hot Breakfast, Indoor Pool-Whirlpool, Fitness Center, Close to Outlet Shopping Mall, less than 3 miles to Lake Michigan, Blue Chip Casino, Indiana Dunes and Splash Dunes Waterpark. More

Hotel only $76

10 Country Inn & Suites By Carlson, Portage, IN

3 stars
4.2 / 5 17 reviews

1630 Olmsted Drive Map

Save 15% on your stay

Portage IN is located on Lake Michigan and has many beaches and parks located on the lake. Please be our guest and enjoy the comforts of home at the charming Country Inn and Suites by Carlson, conveniently located in Portage, IN just off of I-94 at exit 19. Just 35... More

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