Book Exclusive Chesterton Vacation Packages

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Chesterton flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Price was CA $1,459, price is now CA $979 per person
CA $979
per person
Jul 24 - Jul 28
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,547, price is now CA $2,236 per person
CA $2,236
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG

Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG

2.5 out of 5
Price was CA $1,530, price is now CA $1,007 per person
CA $1,007
per person
Jul 24 - Jul 28
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rolling Meadows. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Jump Zone are located nearby.
Four Points by Sheraton Chicago Schaumburg

Four Points by Sheraton Chicago Schaumburg

3 out of 5
Price was CA $1,469, price is now CA $1,011 per person
CA $1,011
per person
Jul 24 - Jul 28
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Spring Valley are located nearby.
Holiday Inn Express Chicago NW - Arlington Heights by IHG

Holiday Inn Express Chicago NW - Arlington Heights by IHG

2.5 out of 5
Price was CA $1,571, price is now CA $1,082 per person
CA $1,082
per person
Jul 24 - Jul 28
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.

Top Chesterton hotels deals

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 $196 per night
CA $196
CA $219 total
Jun 15 - Jun 16
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
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 $180 per night
CA $180
CA $209 total
Jun 15 - Jun 16
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

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 $165 per night
CA $165
CA $185 total
Jun 15 - Jun 16
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 $210 per night
CA $210
CA $236 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this 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
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 $167 per night
CA $167
CA $187 total
Jun 15 - Jun 16
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Spa
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
The price is CA $151 per night
CA $151
CA $169 total
Jul 7 - Jul 8
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
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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

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.

Indiana Dunes State Park
Indiana Dunes National Park Sign

Indiana Dunes Visitor Center

Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area.

Indiana Dunes Visitor Center
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 $979. 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

Viewed on an early Spring day, a wooden staircase along a sandy hillside at Indiana Dunes National Park, near Chesterton, IN.
On a cloudy day in early Springtime, the view of Lake Michigan and the sandy dunes at Indiana Dunes State Park, near Chesterton, IN.
sunset on the beach Indiana Dunes
Father and 1 year old daughter at Indiana Dunes National Park in the summer gazing at Lake Michigan's waves
Indiana Dunes National Park Kemil Beach and Dunbar Beach area. Sunbathers on a rocky beach of Lake Michigan.