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Save up to $413 | Book Flight + Hotel at the same time^
Save up to $413 | Book Flight + Hotel at the same time^
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Save up to $413 | Book Flight + Hotel at the same time^

Chesterton Vacations

Chesterton Vacations

Whether you're setting out on a short and sweet break or a long and leisurely adventure, it's best to know a little bit about Chesterton before setting off.

It's located 6 miles (10 kilometers) away from Portage and 8 miles (13 kilometers) from Westville.

It shouldn't be hard to make some new friends in this part of Northwest Indiana. It boasts a population of roughly 13,000 locals.

Chesterton Vacation Packages

It's as simple as ABC to plan an adventure in Chesterton via Travelocity. Fantastic savings will be all yours when you buy an airfare and accommodation deal. And there's more — you can pick from more than 400 airline companies and 665,000 properties.

Our Customer 1st Guarantee gives you the security of 24/7 personal assistance on everything from flights and accommodations to car rentals and experiences. If you happen to stumble upon a lower price on a different site, we'll refund the difference^.

All travel reservations can be easily altered with no penalty from us. And as long as you get in fast, most accommodations won't charge you either^.

Where to stay in Chesterton

Preparing to tread the path less traveled in Chesterton? Before you dive into that epic adventure, you'll need someplace to stay. Select from our 14 properties and get your escape off on the right foot.

When you've got all those unforgettable vacation experiences to organize, who wants to waste time scouring the web for a place to stay? Don't worry, we've done all the hard work for you. The Best Western Indian Oak are a few of our highly recommended properties in the region.

Where do you fly into for Chesterton?

Heading into Midway International Airport (MDW)? After you've disembarked and collected your luggage, downtown Chesterton will be just 40 miles (64 kilometers) from here.

Can I rent a car in Chesterton?

Going off the beaten track is always an awesome way to experience the local culture. So, how about doing it from behind a steering wheel? Organize a rental vehicle via Travelocity and get ready to crank up the music in Chesterton.

After you've grabbed your luggage at Porter County Municipal Airport, you'll be driving off into the sunset before you know it. Inquire about cars at Enterprise, 11 miles (18 kilometers) from the terminal at 557 S Washington St.

Places to visit in Chesterton

Indiana Dunes State Park is an appealing escape for anyone yearning to get in touch with nature.

Want more options?

Enjoy beautiful scenery and appreciate nature at Indiana Dunes National Lakeshore.

But that's not all.

Go for a walk and enjoy the unspoiled location at Coffee Creek Watershed Conservancy Preserve.

Places to Visit Near Chesterton

If you've explored the offerings of Chesterton already, don't fret. In fact, you've got renowned attractions right around the corner! The Art Institute of Chicago draws people from all continents of the globe. Chicago, about 35 miles (56 kilometers) from Chesterton, is a convenient base when stopping by this world-famous attraction.

^Terms and conditions apply.

Top Chesterton Hotels Deals

$92
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3.0 out of 5.0 501 Gateway Boulevard, Chesterton, IN
4.6/5
(13 Reviews)
This hotel features an indoor pool, a spa tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the fitness center and perks like free self parking.
$68
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5.0 558 Indian Boundary Road, Chesterton, IN
3/5
(12 Reviews)
This hotel features an indoor pool and a 24-hour fitness center. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the steam room and free perks like full breakfast and free self parking.
$51
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

1.5 out of 5.0 713 Plaza Dr., Chesterton, IN
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Free continental breakfast is served. The front desk is staffed around-the-clock and free newspapers are on offer.

Things to do in Chesterton

See all 2 things to do in Chesterton

^Savings based on all package bookings made with Flight + Hotel on Travelocity.com from January 1, 2018 to December 31, 2018, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.