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Chesterton

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Chesterton Flights as Low as $82

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

Frontier Airlines
Wed, Sep 2 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 7 hours ago
$82
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $82 found 7 hours ago
Frontier Airlines
Wed, Sep 2 - Sat, Sep 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 7 hours ago
$83
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 12, priced at $83 found 7 hours ago
Frontier Airlines
Sat, Sep 5 - Sat, Sep 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 7 hours ago
$84
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 12, priced at $84 found 7 hours ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$104 Roundtrip, found 17 hours ago
$104
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $104 found 17 hours ago
JetBlue Airways
Wed, Sep 30 - Sat, Oct 3
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Sep 30 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Oct 3, priced at $159 found 4 hours ago
Delta
Wed, Sep 30 - Thu, Oct 1
LGA
LaGuardia
ORD
O'Hare Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Sep 30 from LaGuardia to O'Hare Intl., returning Thu, Oct 1, priced at $159 found 4 hours ago
American Airlines
Tue, Sep 8 - Sat, Sep 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 17 hours ago
$164
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Sep 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 19, priced at $164 found 17 hours ago
Southwest Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$164 Roundtrip, found 17 hours ago
$164
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $164 found 17 hours ago
United
Tue, Sep 8 - Sat, Sep 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 17 hours ago
$164
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Sep 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 19, priced at $164 found 17 hours ago
Frontier Airlines
Tue, Nov 10 - Sat, Nov 14
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Nov 14, priced at $170 found 1 hour ago
Frontier Airlines
Sun, Aug 30 - Tue, Sep 1
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Sep 1, priced at $171 found 2 days ago
Southwest Airlines
Thu, Sep 17 - Sun, Sep 20
LGA
LaGuardia
MDW
Midway Intl.
$206 Roundtrip, found 22 hours ago
$206
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Thu, Sep 17 from LaGuardia to Midway Intl., returning Sun, Sep 20, priced at $206 found 22 hours ago
Frontier Airlines
Sat, Sep 19 - Tue, Oct 6
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Sep 19 from John F. Kennedy Intl. to Midway Intl., returning Tue, Oct 6, priced at $275 found 3 days ago
American Airlines
Thu, Aug 20 - Mon, Aug 24
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$335 Roundtrip, found 18 hours ago
$335
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Aug 20 from Newark Liberty Intl. Airport to Greater Rockford, returning Mon, Aug 24, priced at $335 found 18 hours ago
American Airlines
Wed, Aug 26 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Aug 30, priced at $347 found 1 day ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$530 Roundtrip, found 23 hours ago
$530
Roundtrip
found 23 hours ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $530 found 23 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 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 $82, 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 $82 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$146

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 helpful staff and the clean rooms in ...
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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. ...
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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! (1,016 reviews)
"Cute hotel. Slightly dated but seems like it’s currently being renovated, so no complaints there. The pool area had a fireplace! I wanna go and swim when that’s running! The breakfast left much to be desired. I am vegan and my options were incredibly limited - the oatmeal packets seemed to be out ..."

Reviewed on Aug 9, 2026

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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 ...
7.8/10 Good! (1,018 reviews)
"The hotel had weird smell and the food made me my kids sick and they didn’t clean our rooms and we had to ask for towels and the tub was clogged up and no one ever answered the front desk phone but overall it could have been better."

Reviewed on Aug 9, 2026

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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! (802 reviews)
"Building is small and old, but the rooms and lobby are updated and bed was very comfortable. Can be a little loud because the upper level has a balcony to the lower level, the noise travels. Did not take advantage of the continental breakfast"

Reviewed on Aug 9, 2026

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Quality Inn Chesterton near Indiana Dunes National Park I-94
Furness Mansion

Furness Mansion

2 out of 5
1491 N Furnleigh Ln Chesterton IN
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes State Park and Indiana Dunes National ...
9/10 Wonderful! (91 reviews)
"We were a bit confused upon arriving because there was no staff present. I forgot to view the message that had the room number and room code in it so once I found that we were great. It was very comfortable and a very nice room. The fire alarm went off right before 7 AM and there was a strong burning ..."

Reviewed on Aug 11, 2026

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Furness Mansion
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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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 ...
6.8/10 (373 reviews)
"The cheapest one in the area"

Reviewed on Aug 9, 2026

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Fairbridge Inn Express Chesterton
See all 1,400 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.