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Chesterton

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Chesterton Flights as Low as $63

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jul 8 - Wed, Jul 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $63 found 1 day ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 17 hours ago
$76
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $76 found 17 hours ago
Frontier Airlines
Tue, Jul 22 - Wed, Jul 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jul 30, priced at $108 found 1 day ago
Spirit Airlines
Wed, Jul 23 - Wed, Jul 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 16 hours ago
$120
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $120 found 16 hours ago
United
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 18 hours ago
$132
Roundtrip
found 18 hours ago
Select United flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 18 hours ago
American Airlines
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 18 hours ago
$132
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 18 hours ago
Delta
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 18 hours ago
$132
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $132 found 18 hours ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $157 found 1 day ago
Frontier Airlines
Mon, Jul 7 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$165 Roundtrip, found 19 hours ago
$165
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Jul 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jul 16, priced at $165 found 19 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 17 hours ago
$191
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 17 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 1 day ago
Contour Airlines
Wed, Jul 16 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Wed, Jul 16 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $203 found 1 day ago
Alaska Airlines
Sat, Sep 27 - Tue, Sep 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$243 Roundtrip, found 16 hours ago
$243
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Sat, Sep 27 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $243 found 16 hours ago
Delta
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jul 14 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 15, priced at $256 found 1 day ago
JetBlue Airways
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$303 Roundtrip, found 17 hours ago
$303
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $303 found 17 hours ago
Sun Country Airlines
Sun, Jul 13 - Mon, Jul 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Jul 13 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $317 found 1 day ago

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 July, 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 16 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 $63, 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 $63 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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 breakfast and the pool in our reviews. ...
8.4/10 Very Good! (1,002 reviews)
"Overall, very good."

Reviewed on Jun 13, 2025

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Best Western Indian Oak
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! (1,009 reviews)
"A pleasant stay! Rooms are spacious and well equipped."

Reviewed on Jun 10, 2025

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Spring House Inn
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! (839 reviews)
"The lake view was wonderful. Unfortunately there was a lot of goose droppings everywhere so you had to watch your step. Staff was nice."

Reviewed on Jun 14, 2025

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Waterbird Lakeside Inn
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! (607 reviews)
"Hotel was in need of updating. 2 story and no elevator. Not a problem for us but might be for others. Staff was extremely nice and helpful. Breakfast was better than expected."

Reviewed on Jun 10, 2025

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Quality Inn Chesterton near Indiana Dunes National Park I-94
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)
"Clean. Quiet. Hot breakfast typical for this type of hotel. Convenient to Indiana Dunes Natl Park where I spent 2.5 days."

Reviewed on Jun 5, 2025

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Comfort Inn & Suites Porter near Indiana Dunes
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 room service. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,000 reviews)
"Courteous friendly staff, relaxing trip"

Reviewed on Jun 4, 2025

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Hilton Garden Inn 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! (1,542 reviews)
"The stay was very nice"

Reviewed on Jun 14, 2025

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Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo
Four Winds Casino Resort – New Buffalo
3.5 out of 5
11111 Wilson Road, New Buffalo, MI
Stay at this 3.5-star business-friendly hotel in New Buffalo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,312 reviews)
"Great food. Very relaxing. Clean. It wasn't one thing, it was a combination of everything."

Reviewed on Jun 14, 2025

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Four Winds Casino Resort – New Buffalo
See all 1,344 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.