Chesterton Vacations 2025/2026 from CA $435

Chesterton flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Grand Royal Hotel O'Hare - Chicago

CA $435

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.

Art Villa

West Town

CA $1,208

per person

Dec 29 - Jan 3

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.

Park Hyatt Chicago

Downtown Chicago

CA $1,369

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $874

per person

Dec 1 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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.

Level Chicago Fulton Market

Downtown Chicago

CA $810

per person

Dec 29 - Jan 3

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Top Chesterton hotels deals

Spring House Inn

303 N Mineral Springs Rd, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $139

CA $162 total

Oct 21 - Oct 22

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

Waterbird Lakeside Inn

556 Indian Boundary Road, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $350

CA $393 total

Oct 31 - Nov 1

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

Best Western Indian Oak

558 Indian Boundary Road, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $131

CA $147 total

Nov 2 - Nov 3

includes taxes & fees

Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the pool and the helpful staff 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

1800 West US Highway 20, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $146

CA $164 total

Nov 6 - Nov 7

includes taxes & fees

Pool

Hot tub

Hilton Garden Inn Chesterton

501 Gateway Boulevard, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $164

CA $184 total

Nov 16 - Nov 17

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

Quality Inn Chesterton near Indiana Dunes National Park I-94

418 Council Road, Chesterton, IN

Free cancellation

Reserve now, pay when you stay

CA $118

CA $132 total

Nov 16 - Nov 17

includes taxes & fees

Breakfast included

Parking included

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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

4/5(1 review)

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

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.

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.

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 $435. 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.