Book Exclusive Chesterton Vacation Packages

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Chesterton flight + hotel packages

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The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $2,387, price is now CA $1,671 per person
CA $1,671
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,585, price is now CA $1,706 per person
CA $1,706
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) 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 $2,709, price is now CA $1,880 per person
CA $1,880
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $3,583, price is now CA $2,497 per person
CA $2,497
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was CA $2,827, price is now CA $2,071 per person
CA $2,071
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Chesterton hotels deals

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
The price is CA $116 per night
CA $116
CA $137 total
Oct 4 - Oct 5
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
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 $157 per night
CA $157
CA $175 total
Oct 6 - Oct 7
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 $126 per night
CA $126
CA $141 total
Oct 18 - Oct 19
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
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 $150 per night
CA $150
CA $168 total
Oct 25 - Oct 26
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
Furness Mansion

Furness Mansion

2 out of 5
1491 N Furnleigh Ln Chesterton IN
The price is CA $169 per night
CA $169
CA $190 total
Oct 7 - Oct 8
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
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 $133 per night
CA $133
CA $149 total
Oct 26 - Oct 27
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
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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 wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

Indiana Dunes State Park

9.0/10 (717 reviews)
You can take time to visit Indiana Dunes State Park during your travels to Chesterton. Wander the beautiful beaches and lakeside in the area.
See properties

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 $1,671. 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.