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Chesterton

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Chesterton Flights as Low as $63

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

Frontier Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 2 days ago
$63
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $63 found 2 days ago
Frontier Airlines
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Feb 25, priced at $68 found 1 day ago
Frontier Airlines
Tue, Feb 18 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Feb 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 25, priced at $68 found 3 days ago
Spirit Airlines
Wed, Jan 8 - Wed, Jan 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jan 8, priced at $88 found 2 days ago
Frontier Airlines
Mon, Jan 13 - Thu, Jan 16
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jan 13 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Jan 16, priced at $118 found 1 day ago
Frontier Airlines
Mon, Feb 3 - Wed, Feb 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 3 from Los Angeles Intl. to Midway Intl., returning Wed, Feb 12, priced at $118 found 1 day ago
Frontier Airlines
Mon, Jan 27 - Sat, Feb 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 9 hours ago
$118
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Jan 27 from Los Angeles Intl. to O'Hare Intl., returning Sat, Feb 1, priced at $118 found 9 hours ago
American Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 2 days ago
Delta
Tue, Jan 7 - Tue, Jan 7
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jan 7 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, Jan 7, priced at $137 found 5 days ago
Delta
Wed, Jan 22 - Wed, Jan 29
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Jan 22 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Jan 29, priced at $137 found 5 days ago
United
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select United flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $137 found 2 days ago
Sun Country Airlines
Fri, Apr 25 - Mon, Apr 28
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Select Sun Country Airlines flight, departing Fri, Apr 25 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Apr 28, priced at $137 found 5 hours ago
Contour Airlines
Wed, Feb 12 - Thu, Feb 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 14 hours ago
$189
Roundtrip
found 14 hours ago
Select Contour Airlines flight, departing Wed, Feb 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Feb 13, priced at $189 found 14 hours ago
Delta
Tue, Feb 4 - Tue, Feb 4
DAL
Love Field
ORD
O'Hare Intl.
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Feb 4 from Love Field to O'Hare Intl., returning Tue, Feb 4, priced at $193 found 2 days ago
Delta
Wed, Jan 29 - Fri, Jan 31
DAL
Love Field
MDW
Midway Intl.
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jan 29 from Love Field to Midway Intl., returning Fri, Jan 31, priced at $206 found 4 days ago
Alaska Airlines
Fri, Jan 24 - Thu, Jan 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$256 Roundtrip, found 9 hours ago
$256
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Fri, Jan 24 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jan 30, priced at $256 found 9 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 February, 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 $63, 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 $63 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$62

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 $100 per night from Dec 22 to Dec 23
$100
includes taxes & fees
Dec 22 - Dec 23
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! (1,000 reviews)
"Love the room! Spacious. And quiet"

Reviewed on Dec 1, 2024

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 Dec 29 to Dec 30
$95
includes taxes & fees
Dec 29 - Dec 30
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! (1,001 reviews)
"This property was perfect except for one thing. The roo overhead light has a motion sensor so if anyone gets up in middle of night qhole room lights up. Very difficu k t to get any rest."

Reviewed on Dec 18, 2024

Best Western Indian Oak
Hilton Garden Inn Chesterton
Hilton Garden Inn Chesterton
3 out of 5
501 Gateway Boulevard, Chesterton, IN
The price is $121 per night from Jan 1 to Jan 2
$121
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (1,000 reviews)
"Very service"

Reviewed on Nov 29, 2024

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 Dec 22 to Dec 23
$91
includes taxes & fees
Dec 22 - Dec 23
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! (785 reviews)
"Beautiful views. Large rooms with comfortable beds. Reasonable rates and friendly staff. Needs some updates here and there, but overall, a nice place to stay. No continental breakfast, but maybe a nice big pot of fresh coffee would of been appreciated rather than the little weak brew they have in ..."

Reviewed on Dec 4, 2024

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 $97 per night from Jan 5 to Jan 6
$97
includes taxes & fees
Jan 5 - Jan 6, 2025
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)
"Clean, comfortable, spacious"

Reviewed on Dec 9, 2024

Comfort Inn & Suites Porter near Indiana Dunes
Furness Mansion
Furness Mansion
2 out of 5
1491 N Furnleigh Ln, Chesterton, IN
The price is $168 per night from Dec 20 to Dec 21
$168
includes taxes & fees
Dec 20 - Dec 21
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes National Park and Kemil Beach are ...
8.4/10 Very Good! (41 reviews)
"."

Reviewed on Nov 7, 2024

Furness Mansion
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 $138 per night from Dec 22 to Dec 23
$138
includes taxes & fees
Dec 22 - Dec 23
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! (1,338 reviews)
"Great place"

Reviewed on Dec 16, 2024

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 $152 per night from Jan 7 to Jan 8
$152
includes taxes & fees
Jan 7 - Jan 8, 2025
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! (1,011 reviews)
Great place
"Great place to stay. Room was very clean and actually had three chairs to sit in!"

Reviewed on Dec 17, 2024

Four Winds Casino Resort – New Buffalo
See all 1,284 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.