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Cheap Flights to Chesterton

Fall in love at first flight with your vacation to Chesterton by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chesterton on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chesterton, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chesterton

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chesterton with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the RFD airport.

What is the cheapest month to fly to Chesterton?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chesterton are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chesterton?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Chesterton.

What airport is best to fly into Chesterton?

When you’re planning your trip to Chesterton, convenience is the name of the game. Luckily, Chesterton Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chesterton must-do list.

How much are flights to Chesterton?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chesterton on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chesterton?

The trick to saving a stack of cash on your flight to Chesterton? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$187

Last Minute Hotel Deals in Chesterton

Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,000 reviews)
"Everything was fine"

Reviewed on Sep 8, 2025

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Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
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. ...
8/10 Very Good! (938 reviews)
"We liked the hospitality. Very nice hostess at the front. Room was okay. Comfy bed. The area surrounding the outside walk up needs updates and fixes. The room inside needs updates for more modern tastes. The batbroom cabinet was broken and wouldn't close completely"

Reviewed on Sep 8, 2025

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Waterbird Lakeside Inn
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
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 ...
8.8/10 Excellent! (1,008 reviews)
"Nice heated pool and sauna. Also was able to build a fire outside in the swinging area around the fire pit!"

Reviewed on Sep 10, 2025

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Spring House Inn
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
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 ...
8/10 Very Good! (1,000 reviews)
"Great service, clean and very comfortable. Good sleep and pleasant breakfast available."

Reviewed on Sep 10, 2025

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Comfort Inn & Suites Porter near Indiana Dunes
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
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 ...
8/10 Very Good! (682 reviews)
Casual and comfortable.
"Stay was comfortable and quiet. Easy check in. Good breakfast. Surrounding city had several dinner options and seemed safe to walk or drive around."

Reviewed on Sep 7, 2025

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Quality Inn Chesterton near Indiana Dunes National Park I-94
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,006 reviews)
"We chose this hotel because it had a pool and laundry facilities, and neither were working when we were there so that was a bit of a disappointment. We were doing a lot of hiking, so a pool/hot tub at the end of the day would have been nice. Also, we needed to do some laundry and couldn't do that ..."

Reviewed on Sep 12, 2025

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Hilton Garden Inn Chesterton
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr., Chesterton, IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
6.6/10 (333 reviews)
"the stay was very great, don’t know why it’s rated so low, it’s a good place in a great location, worth the price"

Reviewed on Aug 31, 2025

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Fairbridge Inn Express Chesterton
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Stay at this 3.5-star spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (1,705 reviews)
Could use some improvement
"Hotel was ok but there are some issues. There is no entrance near the check in desk which is weird, long walk. Exceptionally long wait time to check in. There was only one bar and one bar tender on duty for the whole hotel and casino, long waits. Our room in the old tower was still nice. Parking ..."

Reviewed on Sep 10, 2025

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Blue Chip Casino Hotel and Spa
See all 1,387 properties in Chesterton
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.