Chesterton Vacation Packages

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Flight and hotel packages to Chesterton

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

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 11
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 16 - Jul 20
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking, a library, and express check-in are also offered.

Top Chesterton hotel 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 $110 per night
$110
per night
May 19 - May 20
This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and free perks like continental breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a lobby fireplace are also on offer.
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 $109 per night
$109
per night
May 16 - May 17
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like self-serve breakfast and free self parking.
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 $90 per night
$90
per night
May 19 - May 20
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.
Free WiFi
Parking included
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 $107 per night
$107
per night
May 27 - May 28
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 4 conference rooms, 24-hour business center, and express check-out. Enjoy the spa tub and perks like free self parking.
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 $106 per night
$106
per night
May 27 - May 28
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
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 $122 per night
$122
per night
May 31 - Jun 1
This hotel features a garden, laundry facilities, and free self parking. A picnic area and barbecue grills are also provided.
Pet friendly
Spa
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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 in Chesterton

Image for Indiana Dunes State Park

Indiana Dunes State Park

4.5/5(185 reviews)

The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

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

Bailly Homestead - American Indians and Fur Traders

4.5/5(3 reviews)

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?
Travelocity offers hotel and flight packages starting at an incredible $379. With such amazing bargains, you’ll be exploring all of Chesterton before long.
How long should my Chesterton vacation be?
If you’re looking for some guidance, most visitors spend about 2 nights vacationing in Chesterton. But to discover the true spirit of this place, stay a few extra nights. That way you can tick off more attractions and really soak up the local vibe.
Where can I get the best vacation package deals for Chesterton?
You can pick up sensational Chesterton package deals with Travelocity. Pick and choose from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those vacation dreams into a reality.
Why should I book my Chesterton vacation package via Travelocity?
Because we believe in crafting unforgettable vacation experiences. From hotels and flights to car rentals and activities, our packages make traveling a breeze. Our customer support team is available 24/7 to ensure you’re being well taken care of. We also offer a Price Match Guarantee, so you can lock in your vacation knowing you’ve scored the best deal possible.
Can I save money on my Chesterton car rental if I combine it with my hotel or flight?
Absolutely — bundle your hotel, flight and car into a Chesterton vacation package and you can save a ton. With so many things to do in Chesterton, having your own set of wheels will make exploring a breeze. Once you’ve settled into the driver’s seat, crank up the tunes and make your way to Wrigley Field, a well-known sight about 40 mi from Chesterton.
What is the best time of year to go to Chesterton?
May, June and July are the months when most travelers visit, while December, January and February tend to be less busy. If you have a limited budget, contemplate visiting around . is typically the dearest time to stay here.
Which airport is best for Chesterton?
O’Hare Intl. Airport (ORD) is one of the most popular airports in Chesterton. You’ll find it 50 mi northwest of the bustling downtown area. Other options available to you are South Bend Intl. Airport (SBN) (40 mi away from central Chesterton) and Midway Intl. Airport (MDW) (35 mi away from central Chesterton).
What is there to do in Chesterton?
There’s a certain magic in the air as you stroll through the streets of Chesterton. Coffee Creek Watershed Conservancy Preserve and Lustron House are just two famous attractions that make this city so special, so put them on your to-do list.
Where should I stay when visiting Chesterton?
The Best Western Indian Oak is the first choice of many travelers. Book soon to avoid missing out.