Chesterton Vacations from NT$42,501

Book a Hotel + Flight or Car together to unlock savings

Photo by City Circus Wandering

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chesterton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Great place in Evanston. So close to everything.

Reviewed on 2025/7/31

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on 2025/8/1

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
6.8/10 (822 reviews)
The hotel had no on-site staff. We had to call a phone number to get our room key and were put on hold for a long time. The room only had hand soap—shampoo and conditioner had to be picked up from downstairs. The toilet paper roll in our room was already half used. A perk was receiving three free drinks from the bar next door. A nice spot to check out is Cheesy, located right across the street.

Reviewed on 2025/7/31

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
Room was clean, balcony had a nice view, bed were comfortable, shower was nice

Reviewed on 2025/7/31

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,002 reviews)
Excellent attention from the reception area. And excellent and cordial smilling face

Reviewed on 2025/8/1

Find the Best Chesterton Vacation Packages

Chesterton Hotel Deals

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 NT$3,267 per night from Sep 2 to Sep 3
NT$3,267
NT$3,659 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"We enjoyed staying at the Spring House Inn! The room was clean and spacious. There were great options at the continental breakfast. The staff was friendly & helpful! Our stay was great!"

Reviewed on 2025/7/30

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
The price is NT$3,057 per night from Sep 1 to Sep 2
NT$3,057
NT$3,424 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
It was fine. Probably wouldn’t choose it again.
"This hotel was ok. Not the worst I’ve stayed at and not the best. Front desk seemed frazzled. While the room was mostly clean, there were cigarette butts left on the patio. It was walking distance to several eateries which was helpful."

Reviewed on 2025/7/28

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (896 reviews)
"Nice quiet area"

Reviewed on 2025/8/1

Get rates
Waterbird Lakeside Inn
See all 1,379 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.

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

Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this top destination from NT$42,501 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?
If you're looking to book a cheap Chesterton vacation package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chesterton?
Typically, a few days is enough for a Chesterton vacation. With a carefully crafted itinerary, you can see all the top attractions like Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton vacation guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good vacation destination.
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.
How to plan a trip to Chesterton?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Chesterton.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Chesterton. Then, pick a property that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Chesterton. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the right Chesterton vacation package for you.

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