Chesterton Vacations from $503

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Your Chesterton Vacation

With everything organized before you go away, our Chesterton vacation packages mean you can concentrate on enjoying your getaway. Whether you're based in the neighborhood of Miller Beach, which is good for nature, or somewhere else, this city promises an array of discoveries. A trip to Chesterton is a superb opportunity to see the sights. Make sure you visit well-known attractions like Indiana Dunes National Park, Indiana Dunes State Park and Dune Acres Beach. Stop dreaming and start doing. Check out the range of options on Expedia today and put your Chesterton vacation plans into gear!

The Latest Chesterton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
7.6/10 Good! (6,733 reviews)
Its close to manny atractions manny food places near and it is clean.

Reviewed on May 17, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (1,009 reviews)
Staff very friendly and helpful. Rooms were good. No coffee makers in rooms which is a bit different but each morning complimemtary coffee was available in the lobby. Really good location for us and we would highly reccommend.

Reviewed on May 14, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

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

Chesterton Hotel Deals

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
The price is $110 per night from May 19 to May 20
$110
$123 total
includes taxes & fees
May 19 - May 20
8.4/10 Very Good! (981 reviews)
"The pool and sauna was very nice."

Reviewed on May 16, 2024

Best Western Indian Oak
Spring House Inn
Spring House Inn
2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is $109 per night from May 19 to May 20
$109
$122 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (882 reviews)
"Setting in trees; beautiful unique hotel building. Good breakfast."

Reviewed on May 13, 2024

Spring House Inn
Waterbird Lakeside Inn
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is $90 per night from May 19 to May 20
$90
$101 total
includes taxes & fees
May 19 - May 20
7.8/10 Good! (698 reviews)
"We’ve stayed here many times. The only concern is the sometimes spotty wi-fi. Always comfortable and the wildlife is entertaining, especially the turtles and swallows. Will return."

Reviewed on May 13, 2024

Waterbird Lakeside Inn
See all 1,276 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chesterton vacation package cost?
The cheapest Chesterton package is $503, so your dream escape can become a reality — without a hefty price tag. Combine flights, hotels, car rentals and more to create a package that’s perfect for you.
How do I get a cheap travel package to Chesterton?
Bundling your hotel and flight with Expedia won’t just save precious time — it’ll save you cash too. A Chesterton vacation package makes it simple to put together the ideal trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your busy schedule won’t be a problem. On top of that, we’ve got over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Chesterton?
With fascinating attractions such as Indiana Dunes National Park and Indiana Dunes Visitor Center in this neighborhood, look for a hotel situated near them. Coffee Creek Watershed Conservancy Preserve is another Chesterton sight that people flock to.
What are the top hotels in Chesterton?
One of the most popular places to stay in Chesterton is Hilton Garden Inn Chesterton, in the Porter Beach area. Wander around the city by day and then put your feet up in this comfortable property come nightfall.
How far in advance should I book my Chesterton vacation?
It’s hard to pick the best time for airfares, but we usually say the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you’re booking last minute, don’t despair. Bargain prices occasionally appear just weeks before departure dates.
What does an Expedia Chesterton travel package include?
It all depends on what kind of escape you have in mind. Chesterton travel deals can include car rentals, hotels and flights. You can mix and match to find the package that suits your style and budget. You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking a Chesterton travel package?
Whether it’s adventure or relaxation you’re seeking, a Chesterton vacation package lets you organize your escape your way. Plus, you’ll score great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Chesterton Expedia vacation package?
Yes, you sure can. We offer more than 550 partner airlines across the globe, so opt for the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my Chesterton vacation package?
It is possible to cancel your Chesterton booking if your plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Chesterton

Image for Indiana Dunes State Park

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
Image for Bailly Homestead - American Indians and Fur Traders

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
Image for Waverly Beach

Waverly Beach

Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.

Waverly Beach

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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.