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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.

Spirit Airlines
Tue, May 13 - Tue, May 13
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$82 Roundtrip, found 10 hours ago
$82
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, May 13, priced at $82 found 10 hours ago
Spirit Airlines
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $96 found 6 days ago
Spirit Airlines
Wed, Jun 11 - Wed, Jul 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jun 11 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jul 2, priced at $102 just found
Spirit Airlines
Tue, May 13 - Sat, May 24
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$103 Roundtrip, found 14 hours ago
$103
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, May 24, priced at $103 found 14 hours ago
Spirit Airlines
Tue, May 27 - Mon, Jun 2
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$104 Roundtrip, found 17 hours ago
$104
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Tue, May 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jun 2, priced at $104 found 17 hours ago
Frontier Airlines
Sun, May 25 - Thu, Jun 5
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 19 hours ago
$124
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sun, May 25 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $124 found 19 hours ago
United
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select United flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $157 found 6 days ago
American Airlines
Wed, Jul 9 - Wed, Jul 23
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jul 23, priced at $159 found 3 days ago
Frontier Airlines
Mon, Jun 9 - Thu, Jun 12
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Philadelphia Intl. to O'Hare Intl., returning Thu, Jun 12, priced at $167 found 4 days ago
Bargain Flight
Wed, May 28 - Thu, Jun 5
BUF
Buffalo Niagara Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 16 hours ago
$170
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Wed, May 28 from Buffalo Niagara Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $170 found 16 hours ago
Delta
Tue, May 20 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 20 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $177 found 6 days ago
JetBlue Airways
Tue, May 13 - Wed, May 21
BUF
Buffalo Niagara Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, May 13 from Buffalo Niagara Intl. to O'Hare Intl., returning Wed, May 21, priced at $183 found 1 day ago
Delta
Sat, May 24 - Wed, May 28
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 24 from Raleigh - Durham Intl. to Midway Intl., returning Wed, May 28, priced at $200 found 1 day ago
Frontier Airlines
Sun, May 11 - Thu, May 15
BUF
Buffalo Niagara Intl.
MDW
Midway Intl.
$200 Roundtrip, found 18 hours ago
$200
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sun, May 11 from Buffalo Niagara Intl. to Midway Intl., returning Thu, May 15, priced at $200 found 18 hours ago
Frontier Airlines
Sat, May 17 - Mon, May 19
TTN
Mercer
ORD
O'Hare Intl.
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Mercer to O'Hare Intl., returning Mon, May 19, priced at $214 found 4 days ago
Delta
Sat, May 3 - Sat, May 10
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$411 Roundtrip, found 1 day ago
$411
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 3 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, May 10, priced at $411 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 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 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 $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
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$111

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 $122 per night from May 1 to May 2
$122
includes taxes & fees
May 1 - May 2
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! (1,003 reviews)
"The room was nice and very clean! Very 70s cottage inspired! I love it! Balcony is mesmerizingly beautiful! Bathroom is clean! Enough towels! New bedding! Nice tv! Had Harry Potter and the order of the phoenix had just started when I got in! (I LOVE HP) and they have a nice clean microwave and also ..."

Reviewed on Apr 27, 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 May 6 to May 7
$95
includes taxes & fees
May 6 - May 7
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! (1,003 reviews)
"Wonderful property. Very nice staff. Excellent stay. Would prefer them to have two queens instead of two double beds. Very scenic view. Clean hotel."

Reviewed on Apr 21, 2025

Best Western Indian Oak
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 $91 per night from May 18 to May 19
$91
includes taxes & fees
May 18 - May 19
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)
"Everyone was very nice and helpful. Would definitely stay again!"

Reviewed on Apr 26, 2025

Comfort Inn & Suites Porter near Indiana Dunes
Hilton Garden Inn Chesterton
Hilton Garden Inn Chesterton
3 out of 5
501 Gateway Boulevard, Chesterton, IN
The price is $129 per night from May 19 to May 20
$129
includes taxes & fees
May 19 - May 20
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! (1,003 reviews)
"Excellent staff and very good restaurant!"

Reviewed on Apr 28, 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 May 1 to May 2
$91
includes taxes & fees
May 1 - May 2
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! (810 reviews)
Emergency stay was perfect
"Local power outage at our home made us relocate. Waterbird was awesome"

Reviewed on Apr 26, 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 May 1 to May 2
$140
includes taxes & fees
May 1 - May 2
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! (1,485 reviews)
"Great place"

Reviewed on Apr 27, 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 May 1 to May 2
$115
includes taxes & fees
May 1 - May 2
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! (1,219 reviews)
"Everything is great with the exception of the p"

Reviewed on Apr 26, 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 May 1 to May 2
$62
includes taxes & fees
May 1 - May 2
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)
"Was perfect for price all rooms subject to change"

Reviewed on Apr 28, 2025

Motel 6 Hammond, IN - Chicago Area
See all 1,322 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.