Deals on vacations and trips to Chesterton

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Chesterton flight + hotel vacation packages

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Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $465 per person
$465
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and a free grocery shopping service are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,464, price is now $1,189 per person
$1,189
per person
Oct 12 - Oct 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,890, price is now $1,522 per person
$1,522
per person
Oct 12 - Oct 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,565, price is now $840 per person
$840
per person
Oct 12 - Oct 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,668, price is now $948 per person
$948
per person
Oct 12 - Oct 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.

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
$113 nightly
The price is $127 total per night
$127 total
Sep 2 - Sep 3
Total with taxes and fees
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.
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
$102 nightly
The price is $114 total per night
$114 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Pool
Parking 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
$102 nightly
The price is $115 total per night
$115 total
Aug 25 - Aug 26
Total with taxes and fees
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.
Parking included
Free WiFi
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
$106 nightly
The price is $119 total per night
$119 total
Sep 2 - Sep 3
Total with taxes and fees
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 hot tub and free perks like continental breakfast and free self parking.
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
$92 nightly
The price is $103 total per night
$103 total
Sep 7 - Sep 8
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
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
$129 nightly
The price is $145 total per night
$145 total
Sep 4 - Sep 5
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, 24-hour business center, and express check-out. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
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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 which includes a sandy beach and general coastal views as well as a family

Indiana Dunes State Park

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
This is a very nice place to hike.

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
Michigan lake was a favorite stop and very much like the 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 $465. 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 40 mi 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 50 mi northwest of Chesterton. Your other options are Midway Intl. Airport (MDW) (35 mi away from central Chesterton) and South Bend Intl. Airport (SBN) (40 mi 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