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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 7
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Gorgeous views, great in room dining, staff were very nice

Reviewed on Apr. 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
TV did not work. Was told that it was a problem with the system for everyone and would be fixed in 10 minutes. An hour later I called again and was told the engineer would come to our room next. The engineer never came. No follow up from anyone else. The TV did not work until the next day.

Reviewed on Apr. 29, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Good room, comfortable bed, excellent location.

Reviewed on Apr. 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
I stay here everytime I visit home. Great space and location.

Reviewed on Apr. 29, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr. 28, 2025

Ready to book your vacation to Chesterton?

 

Choose your dates

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 May 5 to May 6
CA $151
CA $169 total
includes taxes & fees
May 5 - May 6
8.8/10 Excellent! (1,003 reviews)
"The room was nice and very clean! Very 70s cottage inspired! I love it! Balcony is mesmerizingly beautiful! Bathroom is clean! Enough towels! New bedding! Nice tv! Had Harry Potter and the order of the phoenix had just started when I got in! (I LOVE HP) and they have a nice clean microwave and also ..."

Reviewed on Apr. 27, 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 $118 per night from May 6 to May 7
CA $118
CA $132 total
includes taxes & fees
May 6 - May 7
8.4/10 Very Good! (1,003 reviews)
"Wonderful property. Very nice staff. Excellent stay. Would prefer them to have two queens instead of two double beds. Very scenic view. Clean hotel."

Reviewed on Apr. 21, 2025

Best Western Indian Oak
Comfort Inn & Suites Porter near Indiana Dunes
Comfort Inn & Suites Porter near Indiana Dunes
2.5 out of 5
1800 West US Highway 20, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from May 18 to May 19
CA $112
CA $125 total
includes taxes & fees
May 18 - May 19
8/10 Very Good! (1,003 reviews)
"Everyone was very nice and helpful. Would definitely stay again!"

Reviewed on Apr. 26, 2025

Comfort Inn & Suites Porter near Indiana Dunes
See all 1,323 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this popular destination from CA $842 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.