Chesterton Vacations from $212

Book a Hotel + Flight or Car together to unlock savings

Photo by City Circus Wandering

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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $361, price is now $212 per person
$212
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast are fresh. Shops are near by.

Reviewed on Oct 10, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $455, price is now $225 per person
$225
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $559, price is now $318 per person
$318
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
8.2/10 Very Good! (1,009 reviews)
Nothing to complain about. It’s an okay place.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,001, price is now $576 per person
$576
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

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Discover the most popular places to visit in Chesterton

Indiana Dunes State Park which includes a sandy beach and general coastal views as well as a family

Indiana Dunes State Park

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
This is a very nice place to hike.

Bailly Homestead - American Indians and Fur Traders

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

Indiana Dunes Visitor Center

Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area.

Indiana Dunes Visitor Center

Chesterton Hotel Deals

Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from Nov 2 to Nov 3
$101 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (961 reviews)
"Parking seemed safe enough. The building is older and in need of attention. Broken window pane on one of the upstairs window. One light in my room didnt function and the bathroom door was splintering at the bottom. Room was clean! Though the building was in need of update and repair it was clean! ..."

Reviewed on Oct 8, 2025

Waterbird Lakeside Inn
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
$103 nightly
The price is $116 total per night from Oct 12 to Oct 13
$116 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
"Our stay at the Spring House Inn was fine. It wasn't stellar, it wasn't awful. The place is dated. And every creaking floor tells that story. There is a weird smell throughout - if it's not bleach, it's something floral mixed with bleach and all the halls had Glade Plug Ins in them. Breakfast was ..."

Reviewed on Oct 7, 2025

Spring House Inn
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
$93 nightly
The price is $105 total per night from Nov 2 to Nov 3
$105 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Ac was great, room was spacious and comfortable, patio view was very nice, National and State Park near by, great restaurant selections and some within walking distance. Rooms were clean, plenty of parking, and a very quiet area."

Reviewed on Oct 6, 2025

Best Western Indian Oak
See all 1,393 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.

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

How much does a Chesterton vacation package cost?
You can grab a vacation package to this top destination from $212 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.

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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.