Chesterton Vacation Packages

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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.

Top Chesterton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was CA $1,080, price is now CA $621 per person
CA $621
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on Aug. 22, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,315, price is now CA $788 per person
CA $788
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,118 per person
CA $1,118
per person
Nov 21 - Nov 24
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was CA $1,699, price is now CA $1,070 per person
CA $1,070
per person
Oct 6 - Oct 10
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on Aug. 24, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $2,075, price is now CA $1,322 per person
CA $1,322
per person
Nov 3 - Nov 6
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
10/10 Exceptional! (2 reviews)

Ready to book your vacation to Chesterton?

 

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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 CA $151 per night from Sep 2 to Sep 3
CA $151
CA $176 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Charm"

Reviewed on Aug. 22, 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
The price is CA $141 per night from Sep 2 to Sep 3
CA $141
CA $158 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Very lovely place to stay. The lake is very pretty with lots of wildlife. Although the hotel is older, it is very quaint. It is also very quiet, the staff were very pleasant and helpful, and the room and bathroom were so very nice. I’d definitely stay here again."

Reviewed on Aug. 18, 2025

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
The price is CA $134 per night from Aug 27 to Aug 28
CA $134
CA $150 total
Aug 27 - Aug 28
includes taxes & fees
8/10 Very Good! (912 reviews)
"A quiet place to stay overlooking a lovely lake. We really enjoyed having the balcony over the water. The staff were very kind and helpful as well."

Reviewed on Aug. 24, 2025

Waterbird Lakeside Inn
See all 1,376 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this popular destination from CA $621 on Expedia. But how much your vacation to Chesterton costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Chesterton?
December, January and February are the best times to look for cheap Chesterton vacation packages. Choosing to travel in quieter periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Chesterton?
You can easily visit all the top attractions in Chesterton in a few days, including the must-see Coffee Creek Watershed Conservancy Preserve. If you're looking for a longer Chesterton vacation, look at which kind of activities and day trips are available nearby.
Is it worth booking a vacation package to Chesterton?
Boasting a host of highlights starting with its amazing golfing, Chesterton is a good vacation destination. Whether you'd like to discover attractions like Coffee Creek Watershed Conservancy Preserve and Lustron House or venture off the beaten track, you'll find loads to see and do on your Chesterton vacation.
How to find the best Chesterton package deals?
Use Expedia's filter tool to find some terrific Chesterton package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chesterton package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Chesterton vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Chesterton vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chesterton?
If you're considering a spontaneous Chesterton adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Chesterton?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Chesterton.
  2. Set a budget: Consider expenses such as transportation, flights and meals when working out how much to put aside for your trip to Chesterton. Then, select a property that works with your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Chesterton. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Chesterton vacation package.

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