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Chesterton

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Chesterton Flights as Low as $80

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

Spirit Airlines
Mon, May 19 - Sun, May 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 25, priced at $80 found 1 hour ago
Frontier Airlines
Sat, May 17 - Sat, May 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 1 hour ago
$94
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 17 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 17, priced at $94 found 1 hour ago
Frontier Airlines
Tue, May 6 - Tue, May 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 6, priced at $98 found 1 hour ago
Frontier Airlines
Wed, May 14 - Tue, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 20, priced at $100 found 1 hour ago
Frontier Airlines
Wed, May 7 - Mon, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$101 Roundtrip, found 1 hour ago
$101
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, May 12, priced at $101 found 1 hour ago
Spirit Airlines
Tue, May 27 - Wed, Jun 4
LGA
LaGuardia
ORD
O'Hare Intl.
$111 Roundtrip, found 3 days ago
$111
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 27 from LaGuardia to O'Hare Intl., returning Wed, Jun 4, priced at $111 found 3 days ago
Spirit Airlines
Tue, Jun 10 - Tue, Jun 10
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 10 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $130 found 1 hour ago
Delta
Sat, May 17 - Sat, May 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 1 hour ago
$154
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 17 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 17, priced at $154 found 1 hour ago
American Airlines
Sat, May 17 - Sat, May 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 1 hour ago
$154
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, May 17 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 17, priced at $154 found 1 hour ago
Spirit Airlines
Tue, Jun 3 - Wed, Jun 11
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Harry Reid Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $157 found 1 hour ago
United
Sat, May 31 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select United flight, departing Sat, May 31 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jun 4, priced at $159 found 1 hour ago
Delta
Tue, Jul 22 - Wed, Jul 23
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jul 22 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Wed, Jul 23, priced at $217 found 1 hour ago
Frontier Airlines
Tue, Apr 15 - Tue, Apr 22
LGA
LaGuardia
MDW
Midway Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Apr 15 from LaGuardia to Midway Intl., returning Tue, Apr 22, priced at $230 found 4 days ago
Frontier Airlines
Fri, Jun 27 - Sat, Jul 12
LAS
Harry Reid Intl.
MDW
Midway Intl.
$242 Roundtrip, found 1 hour ago
$242
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jun 27 from Harry Reid Intl. to Midway Intl., returning Sat, Jul 12, priced at $242 found 1 hour ago
JetBlue Airways
Wed, May 7 - Wed, May 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$279 Roundtrip, found 1 hour ago
$279
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 14, priced at $279 found 1 hour ago
Alaska Airlines
Tue, Jun 3 - Wed, Jun 11
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$312 Roundtrip, found 1 hour ago
$312
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Jun 3 from Harry Reid Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $312 found 1 hour 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 May, 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 $80, 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 $80 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$100

Last Minute Hotel Deals in Chesterton

Spring House Inn
Spring House Inn
2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
The price is $111 per night from Apr 15 to Apr 16
$111
includes taxes & fees
Apr 15 - Apr 16
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! (1,001 reviews)
"It was family friendly but also it was quiet enough for my husband's and mine mini get away weekend."

Reviewed on Apr 7, 2025

Spring House Inn
Best Western Indian Oak
Best Western Indian Oak
2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
The price is $95 per night from Apr 21 to Apr 22
$95
includes taxes & fees
Apr 21 - Apr 22
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)
"The room was very clean as expected and the staff was very kind and helpful when I had questions."

Reviewed on Apr 8, 2025

Best Western Indian Oak
Hilton Garden Inn Chesterton
Hilton Garden Inn Chesterton
3 out of 5
501 Gateway Boulevard, Chesterton, IN
The price is $117 per night from Apr 20 to Apr 21
$117
includes taxes & fees
Apr 20 - Apr 21
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! (1,005 reviews)
"Hotel was really nice and clean overall, just a few small things, our vent fan in the bathroom didn't work and the TV was finicky to turn on."

Reviewed on Apr 12, 2025

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
The price is $101 per night from May 7 to May 8
$101
includes taxes & fees
May 7 - May 8
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! (1,002 reviews)
"It was very welcoming! Pool and hot tub were hreat"

Reviewed on Apr 2, 2025

Comfort Inn & Suites Porter near Indiana Dunes
Waterbird Lakeside Inn
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
The price is $86 per night from Apr 15 to Apr 16
$86
includes taxes & fees
Apr 15 - Apr 16
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! (805 reviews)
"Nothing special"

Reviewed on Apr 13, 2025

Waterbird Lakeside Inn
Blue Chip Casino Hotel and Spa
Blue Chip Casino Hotel and Spa
3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
The price is $140 per night from Apr 15 to Apr 16
$140
includes taxes & fees
Apr 15 - Apr 16
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! (1,472 reviews)
"Had a great time"

Reviewed on Apr 11, 2025

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
The price is $115 per night from Apr 15 to Apr 16
$115
includes taxes & fees
Apr 15 - Apr 16
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! (1,191 reviews)
"Large, nice casino on a beautiful wooded property. Lots of deer on the drive in. Great staff. Big, clean rooms."

Reviewed on Apr 11, 2025

Four Winds Casino Resort – New Buffalo
Fairfield Inn and Suites By Marriott Merrillville
Fairfield Inn and Suites By Marriott Merrillville
2.5 out of 5
8275 Georgia St, Merrillville, IN
The price is $99 per night from Apr 27 to Apr 28
$99
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,004 reviews)
"It was close to our tournament thats why we like. Service is really good."

Reviewed on Apr 13, 2025

Fairfield Inn and Suites By Marriott Merrillville
See all 1,323 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.