Chesterton Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,106, price is now CA $794 per person
CA $794
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

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 $128 per night from Nov 18 to Nov 19
CA $128
CA $151 total
Nov 18 - Nov 19
includes taxes & fees
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
The price is CA $126 per night from Nov 17 to Nov 18
CA $126
CA $141 total
Nov 17 - Nov 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Clean well maintain room pleasant staff better than most bfast wasynparking and access to freeway and monouteqfeous upcharge for notre dame home football weekend dates"

Reviewed on Nov 10, 2026

Best Western Indian Oak
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr. Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Dec 12 to Dec 13
CA $123
CA $138 total
Dec 12 - Dec 13
includes taxes & fees
Fairbridge Inn Express Chesterton
See all 1,463 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

Stay near popular Chesterton attractions

A sandy beach with the ocean in the background and a grassy hill with trees.

Indiana Dunes State Park

9.0/10 (717 reviews)
The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.
See properties

Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this popular destination from CA $671 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.