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Chesterton

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Chesterton Flights as Low as $60

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

Frontier Airlines
Tue, Sep 23 - Tue, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$60 Roundtrip, found 13 hours ago
$60
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Sep 23 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Sep 30, priced at $60 found 13 hours ago
Spirit Airlines
Tue, Aug 12 - Tue, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 6 hours ago
$72
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $72 found 6 hours ago
Frontier Airlines
Mon, Aug 25 - Wed, Aug 27
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $87 found 2 days ago
Frontier Airlines
Thu, Oct 2 - Tue, Oct 7
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Oct 7, priced at $90 found 1 day ago
Delta
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $132 found 2 days ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 19 hours ago
$134
Roundtrip
found 19 hours ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $134 found 19 hours ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $134 found 2 days ago
Bargain Flight
Sat, Nov 8 - Sat, Nov 8
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$182 Roundtrip, found 6 hours ago
$182
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Sat, Nov 8 from Seattle - Tacoma Intl. to O'Hare Intl., returning Sat, Nov 8, priced at $182 found 6 hours ago
Delta
Tue, Aug 26 - Tue, Aug 26
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 26 from Love Field to O'Hare Intl., returning Tue, Aug 26, priced at $191 found 1 day ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 1 day ago
$193
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 $193 found 1 day ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 5 hours ago
Frontier Airlines
Sun, Aug 3 - Wed, Aug 13
FSD
Sioux Falls Regional
ORD
O'Hare Intl.
$201 Roundtrip, found 6 hours ago
$201
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, Aug 3 from Sioux Falls Regional to O'Hare Intl., returning Wed, Aug 13, priced at $201 found 6 hours ago
Hawaiian Airlines
Wed, Sep 3 - Sun, Sep 7
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Wed, Sep 3 from Seattle - Tacoma Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $206 found 4 days ago
Frontier Airlines
Thu, Aug 14 - Sat, Aug 16
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$263 Roundtrip, found 5 hours ago
$263
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Seattle - Tacoma Intl. to Midway Intl., returning Sat, Aug 16, priced at $263 found 5 hours ago
Frontier Airlines
Fri, Aug 22 - Mon, Aug 25
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 22 from Seattle Paine Field Intl. Airport to O'Hare Intl., returning Mon, Aug 25, priced at $268 found 1 day ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 6 hours ago
$272
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $272 found 6 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 September, 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 15 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 $60, 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 $60 right now, why wait?

Chesterton Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$60

Last Minute Hotel Deals in Chesterton

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! (1,022 reviews)
"Easy check in although there is no early check in option but the room was clean and comfortable. Breakfast has an adequate selection but all of the egg and sausage options offered were cold at 7 am when the breakfast opened so we had to heat that up in our room’s microwave because there isn’t a microwave ..."

Reviewed on Jul 28, 2025

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Spring House Inn
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! (1,009 reviews)
"all good"

Reviewed on Jul 24, 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! (886 reviews)
"Mattress and sheets were fantastic- lake view is awesome!"

Reviewed on Jul 21, 2025

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Waterbird Lakeside Inn
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! (1,004 reviews)
"The staff member that greeted me was so nice and personable."

Reviewed on Jul 27, 2025

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Hilton Garden Inn 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! (1,008 reviews)
Awesome service and staff!!
"The staff are great and so sweet. Very attentive to their guests. Whatever I needed, they got for me right away. Continental breakfast is awesome. Complimentary lemon water in lobby is great as well. Pool and spa are awesome. This is my 2nd time staying here and I WILL BE BACK!"

Reviewed on Jul 25, 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! (646 reviews)
Great friendly place and reasonably priced
"Fabulous - warm & friendly welcome, clean room, great window blackout curtains, comfy bed, topped off by a good breakfast! Heat your own turkey sausage burrito and waffles! Definitely a great value!"

Reviewed on Jul 22, 2025

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Quality Inn Chesterton near Indiana Dunes National Park I-94
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 (316 reviews)
"This place is like my second home"

Reviewed on Jul 22, 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! (1,634 reviews)
"The staff was great. The ac in my room wasn't working and they moved me into a much better room. The hotel is very nice and bright. Only issue was the heavy smoke smell in the casino but the hotel itself was great."

Reviewed on Jul 24, 2025

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Blue Chip Casino Hotel and Spa
See all 1,378 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.