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Chesterton

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Chesterton Flights as Low as $75

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

Spirit Airlines
Tue, Jul 22 - Tue, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 14 hours ago
$75
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $75 found 14 hours ago
Frontier Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 6, priced at $90 found 3 days ago
Frontier Airlines
Fri, Aug 15 - Sun, Aug 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $90 found 3 days ago
Frontier Airlines
Tue, Jul 29 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $112 found 5 days ago
Spirit Airlines
Wed, Sep 24 - Sat, Sep 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Sep 24 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $130 found 4 days ago
Delta
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 12 hours ago
$132
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 12 hours ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 12 hours ago
$132
Roundtrip
found 12 hours ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 12 hours ago
American Airlines
Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 14 hours ago
$132
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 14 hours ago
Spirit Airlines
Tue, Nov 4 - Tue, Nov 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$132 Roundtrip, found 17 hours ago
$132
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Tue, Nov 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Nov 11, priced at $132 found 17 hours ago
Frontier Airlines
Tue, Jul 15 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jul 23, priced at $139 found 4 days ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $189 found 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 13 hours ago
$191
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 13 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 22 hours ago
$197
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 22 hours ago
Alaska Airlines
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 14 hours ago
$216
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 found 14 hours ago
Delta
Sat, Jul 12 - Tue, Jul 15
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$251 Roundtrip, found 4 days ago
$251
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jul 12 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Jul 15, priced at $251 found 4 days ago
Delta
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 9 hours ago
$255
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $255 found 9 hours 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 $75, 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 $75 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$112

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! (1,000 reviews)
"The room was nice and clean. The dining area was too small for the mornings we were there and insufficient kitchen equipment. Highly recommend having two waffle making stations at different locations. Also recommend two toasters. Both of these stations had lines the entire time I wae eating."

Reviewed on Jul 1, 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)
"Would love to come back again! Enjoyed sauna and pool in the evening. Very close to Indiana Dunes National and State parks, and nice restaurants. Our room patio faced a beautiful forest. Very relaxing and tranquil stay!"

Reviewed on Jul 3, 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! (860 reviews)
"The view off the balcony is great"

Reviewed on Jul 4, 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! (628 reviews)
"Good stay. Our room had nonfunctional air conditioning so we were able to get another room."

Reviewed on Jul 6, 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! (1,001 reviews)
"We loved staying here."

Reviewed on Jun 26, 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 (303 reviews)
"Everyone was friendly and helpful"

Reviewed on Jun 30, 2025

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Fairbridge Inn Express Chesterton
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)
"Awesome staff and property. Close to area attractions. Clean and comfy rooms. Nice little breakfast as well"

Reviewed on Jul 1, 2025

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Comfort Inn & Suites Porter near Indiana Dunes
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! (1,577 reviews)
"Great place"

Reviewed on Jul 5, 2025

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Blue Chip Casino Hotel and Spa
See all 1,369 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.