Book Exclusive Chesterton Vacation Packages

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Chesterton flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4-star 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 5-star 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff 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
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise 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
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $198 total
Aug 3 - Aug 4
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 $151 per night
CA $151
CA $170 total
Aug 13 - Aug 14
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Pool
Breakfast included
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 $164 per night
CA $164
CA $184 total
Aug 3 - Aug 4
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
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $158 per night
CA $158
CA $177 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), 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
Pet-friendly
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
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $176 total
Aug 24 - Aug 25
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
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
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $129 total
Aug 25 - Aug 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.
Breakfast included
Parking included
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See all available properties in Chesterton
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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.

Popular places to visit

Indiana Dunes State Park showing general coastal views and a beach as well as a family

Indiana Dunes State Park

You can take time to visit Indiana Dunes State Park during your travels to Chesterton. Wander the beautiful beaches and lakeside in the area.

Indiana Dunes State Park
Bailly Homestead - American Indians and Fur Traders

Bailly Homestead - American Indians and Fur Traders

You can find out about the history of Porter with a stop at Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.

Bailly Homestead - American Indians and Fur Traders
Waverly Beach

Waverly Beach

Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.

Waverly Beach

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 $1,599. 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

Photo provided by Indiana Office of Tourism Development
Photo provided by Indiana Office of Tourism Development
Chesterton
Chesterton
Chesterton
Photo by Susan Ross
Photo by Susan Ross