Book Exclusive Chesterton Vacation Packages

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Chesterton flight + hotel packages

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JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willis Tower and Millennium Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul. 5 - Jul. 8
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 restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 31 - Aug. 5
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 $150 per night
CA $150
per night
May 14 - May 15
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.
Breakfast included
Pool
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 $149 per night
CA $149
per night
May 16 - May 17
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
Pool
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 $123 per night
CA $123
per night
May 20 - May 21
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Parking included
Laundry
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 $145 per night
CA $145
per night
May 27 - May 28
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and room service. 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.
Hot tub
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 $144 per night
CA $144
per night
May 21 - May 22
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a 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.
Hot tub
Pool
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 $175 per night
CA $175
per night
May 15 - May 16
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.
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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

Image for Indiana Dunes State Park

Indiana Dunes State Park

4/5(1 review)

Explore the great outdoors at Indiana Dunes State Park, a lovely green space in Chesterton. Wander the beautiful beaches and lakeside in the area.

Indiana Dunes State Park
Image for 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
Image for 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?
CA $758 is all you’ll need for an unforgettable vacation in Chesterton. Bundle your flights and hotel into a vacation package with Travelocity and watch the savings start to add up. With prices as good as these, you’ll want to start packing your bags now!
How long should my Chesterton vacation be?
Many travelers reserve a hotel for 2 nights in Chesterton. But that doesn’t necessarily mean you’re limited to that. How long you choose to stay really boils down to what you hope to do during your vacation. If you want to explore every square inch of this superb destination, consider staying another few nights (or even longer!).
Where can I get the best vacation package deals for Chesterton?
Landing the best package deal to Chesterton is a piece of cake with Travelocity. With 400 air carriers and 665,000 properties across the globe, you’ll have loads of choice when picking your flights and hotels.
Why should I purchase my Chesterton vacation bundle with Travelocity?
Because you’ll never roam alone if you book your trip with us, and we offer round-the-clock customer support and high-quality service to boot. Add to that our Price Match Guarantee and a huge range of experiences to select from. We’re here to help you have the trip of a lifetime.
Can I save on my Chesterton car rental if I bundle it with my hotel or flight?
Combining your hotel, car and flight into a Chesterton vacation package is a great way to score an incredible deal. Plus, having your own set of wheels gives you freedom to make your way to all those big-name sights you’re itching to explore. Situated 64 kilometersfrom Chesterton, Wrigley Field is one place that should have a place on your itinerary. Turn up the tunes and make a day trip of it.
What is the best time of year to go to Chesterton?
Visiting in the least busy months, , comes with advantages — think more cost-effective flights and hotels and less grappling with hordes of strangers. But there’s magic in the air in the busiest season. More events are likely to be on and more attractions will be open in . If you’re watching your budget, generally has the cheapest hotel rates. Expect to pay more for a bed in .
Which airport is best for Chesterton?
Chicago, IL (ORD-O’Hare Intl.) is one of the most popular airports in Chesterton. It’s located 80 kilometersnorthwest of the downtown area. Other choices include Chicago, IL (MDW-Midway Intl.) (60 kilometersaway from central Chesterton) and South Bend, IN (SBN-South Bend Intl.) (64 kilometersaway from central Chesterton).
What is there to do in Chesterton?
Indiana Dunes State Park is just one of the memorable sights that make Chesterton such a popular tourist destination. But allow yourself enough time to explore the city’s lesser-known attractions too. This is sometimes where the best vacation memories are made.
Where should I stay when visiting Chesterton?
The Waterbird Lakeside Inn (2.0 stars) and the Fairbridge Inn Express Chesterton (1.5 stars) are fantastic options for those visiting Chesterton on a shoestring.
Can I go on vacation to Chesterton at this time?
Don’t take off to Chesterton without the facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor can fill you in. Our travel experts have pulled together all the information you need to make your getaway as stress-free as possible.