Book Exclusive Chesterton Vacation Packages

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Chesterton flight + hotel packages

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
Price was CA $1,526, price is now CA $1,062 per person
CA $1,062
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,285, price is now CA $1,569 per person
CA $1,569
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,264, price is now CA $1,571 per person
CA $1,571
per person
Oct 20 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,974, price is now CA $1,405 per person
CA $1,405
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,088, price is now CA $1,524 per person
CA $1,524
per person
Oct 20 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Chesterton hotels deals

Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $176 total
Aug 11 - Aug 12
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Parking included
Free WiFi
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $193 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Pool
Breakfast included
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
Free cancellation
The price is CA $159 per night
CA $159
CA $178 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Pool
Hot tub
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
Free cancellation
Reserve now, pay when you stay
The price is CA $154 per night
CA $154
CA $172 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Pool
Breakfast included
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 out of 5
418 Council Road Chesterton IN
Free cancellation
The price is CA $127 per night
CA $127
CA $142 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Breakfast included
Parking included
Furness Mansion

Furness Mansion

2 out of 5
1491 N Furnleigh Ln Chesterton IN
Free cancellation
Reserve now, pay when you stay
The price is CA $155 per night
CA $155
CA $173 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes State Park and Indiana Dunes National Park are located nearby.
Spa
Pet-friendly
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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.

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)
Indiana Dunes State Park is one of the more well-known attractions to visit during your trip to Chesterton. Wander the beautiful beaches and lakeside in the area.
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Frequently asked questions

How much are vacation packages to Chesterton?
Treat yourself to an unforgettable experience in Chesterton with a vacation package starting at CA $1,062. Locking in your flights, tours and hotels with Travelocity is so easy. What's more, our vacation deals will leave you with extra money for loads of fun activities.
How long should my Chesterton vacation be?
Your Chesterton getaway can be as short or as long as you'd like it to be, but the majority of people stay roughly 2 nights. Want to get out and uncover some lesser-known sights? Stay a few extra nights and see a different side of this destination.
Where can I get the best vacation package deals for Chesterton?
There are awesome Chesterton package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep this in mind when you're ready to check another destination off your list.
Why should I book my Chesterton vacation package with Travelocity?
Whether you're planning a weeks-long vacation or a last-minute trip, we have plenty of amazing destinations to choose from at a good price. What's more, we offer 24/7 support, excellent service and a Price Match Guarantee. Save yourself time and money and reserve your dream vacation today.
Will I save money on my Chesterton car rental if I book it with my hotel or flight?
Bundling your hotel, flight and car into a Chesterton vacation package is an excellent way to score an amazing deal. Plus, having your own set of wheels gives you freedom to make your way to all those amazing sights you're itching to see. Located 64 kilometers from Chesterton, Wrigley Field is one place that should be on your must-do list. Turn up the tunes and make a day trip of it.
Which airport is best for Chesterton?
O'Hare Intl. Airport (ORD) is popular. You'll find it approximately 80 kilometers northwest of Chesterton. Your other options are Midway Intl. Airport (MDW) (56 kilometers away from central Chesterton) and South Bend Intl. Airport (SBN) (64 kilometers away from central Chesterton).
What is there to do in Chesterton?
You'll notice a certain magic as you stroll the streets of Chesterton. Dune Acres Beach and Coffee Creek Watershed Conservancy Preserve are just a couple of highlights that entice visitors to this wonderful city, so put them on your list of places to see.
Where should I stay when visiting Chesterton?
Many visitors opt to hit the hay at the Spring House Inn. It's a terrific base for your Chesterton vacation.

Photos of local treasures

Browse Chesterton vacation photos for more inspiration

A wooden staircase ascending a sandy hill with sparse vegetation.
A beach with sand dunes and sparse vegetation.
A beach with waves and two people standing on the shore.
A man and a child holding hands on a beach with waves in the background.
A pebbly beach with a few people and a yellow umbrella.