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Chesterton

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Chesterton Flights as Low as $48

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

Frontier Airlines
Tue, Mar 11 - Wed, Mar 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$48 Roundtrip, found 3 days ago
$48
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Mar 11 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Mar 12, priced at $48 found 3 days ago
Frontier Airlines
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$48 Roundtrip, found 6 days ago
$48
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $48 found 6 days ago
Frontier Airlines
Tue, Mar 18 - Tue, Mar 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 1 day ago
$48
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Mar 25, priced at $48 found 1 day ago
Spirit Airlines
Tue, Mar 18 - Tue, Apr 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 3 days ago
$48
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Mar 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $48 found 3 days ago
Frontier Airlines
Wed, Mar 12 - Wed, Mar 19
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$49 Roundtrip, found 3 days ago
$49
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 12 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Wed, Mar 19, priced at $49 found 3 days ago
Frontier Airlines
Tue, Mar 4 - Sat, Mar 8
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Mar 8, priced at $110 found 1 day ago
Frontier Airlines
Sat, Mar 8 - Wed, Mar 12
TTN
Mercer
MDW
Midway Intl.
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Mar 8 from Mercer to Midway Intl., returning Wed, Mar 12, priced at $111 found 6 days ago
Frontier Airlines
Sat, Mar 1 - Tue, Mar 4
TTN
Mercer
ORD
O'Hare Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Mercer to O'Hare Intl., returning Tue, Mar 4, priced at $135 found 1 day ago
United
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
Select United flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $139 found 6 days ago
American Airlines
Tue, Apr 22 - Tue, Apr 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 22, priced at $177 found 3 days ago
Delta
Tue, Apr 22 - Tue, Apr 22
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, Apr 22, priced at $191 found 2 days ago
Frontier Airlines
Tue, Feb 25 - Wed, Feb 26
IAH
George Bush Intercontinental
MDW
Midway Intl.
$201 Roundtrip, found 17 hours ago
$201
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Feb 25 from George Bush Intercontinental to Midway Intl., returning Wed, Feb 26, priced at $201 found 17 hours ago
Delta
Sat, Mar 8 - Tue, Mar 11
DAL
Love Field
ORD
O'Hare Intl.
$217 Roundtrip, found 13 hours ago
$217
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Mar 8 from Love Field to O'Hare Intl., returning Tue, Mar 11, priced at $217 found 13 hours ago
Delta
Sat, Apr 12 - Tue, Apr 15
DAL
Love Field
MDW
Midway Intl.
$218 Roundtrip, found 5 days ago
$218
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Apr 12 from Love Field to Midway Intl., returning Tue, Apr 15, priced at $218 found 5 days ago
Contour Airlines
Fri, Mar 21 - Mon, Mar 24
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Fri, Mar 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Mar 24, priced at $230 found 1 day ago
Alaska Airlines
Thu, Jul 3 - Mon, Jul 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$22,222 Roundtrip, found 1 day ago
$22,222
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Jul 3 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $22,222 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 March, 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 $48, 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 $48 right now, why wait?

Chesterton Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$42

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 $88 per night from Feb 23 to Feb 24
$88
includes taxes & fees
Feb 23 - Feb 24
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! (1,002 reviews)
"We love this place! It’s close, quiet, quaint. We love UNOs pizza!! We had the pool to ourselves!! Thank you!"

Reviewed on Feb 19, 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 Feb 26 to Feb 27
$95
includes taxes & fees
Feb 26 - Feb 27
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)
"Great easy check in with kind staff ! Clean hotel with close proximity to so many stores ! We arrived on a snowy day and they had a truck and plow on it ! Would recommend !"

Reviewed on Feb 17, 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 $112 per night from Mar 2 to Mar 3
$112
includes taxes & fees
Mar 2 - Mar 3
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! (1,001 reviews)
"Everything ok; very noisy heating system"

Reviewed on Feb 18, 2025

Hilton Garden Inn Chesterton
Waterbird Lakeside Inn
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
The price is $91 per night from Feb 23 to Feb 24
$91
includes taxes & fees
Feb 23 - Feb 24
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! (793 reviews)
"The sheets were so comfortable, the room was spacious, and the view over the lake was lovely:"

Reviewed on Jan 14, 2025

Waterbird Lakeside 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
The price is $87 per night from Feb 23 to Feb 24
$87
includes taxes & fees
Feb 23 - Feb 24
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! (999 reviews)
"I would give five stars but I didn't get the room I originally booked."

Reviewed on Feb 16, 2025

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
The price is $131 per night from Feb 23 to Feb 24
$131
includes taxes & fees
Feb 23 - Feb 24
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! (1,416 reviews)
"Everything met my expectations. Will probably stay there again."

Reviewed on Feb 19, 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 Feb 24 to Feb 25
$115
includes taxes & fees
Feb 24 - Feb 25
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! (1,086 reviews)
Nice stay
"Our stay was good. The room service menu was pleasing and the pricing was good. I give the room service workers 10/10. The pillows were not to my liking. That’s my only complaint. Overall it was a nice stay and we will be staying again."

Reviewed on Feb 17, 2025

Four Winds Casino Resort – New Buffalo
Motel 6 Hammond, IN - Chicago Area
Motel 6 Hammond, IN - Chicago Area
2 out of 5
3840 179th St, Hammond, IN
The price is $62 per night from Feb 23 to Feb 24
$62
includes taxes & fees
Feb 23 - Feb 24
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.2/10 (1,000 reviews)
5 stars
"All around good place and great staff"

Reviewed on Feb 10, 2025

Motel 6 Hammond, IN - Chicago Area
See all 1,292 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.