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Chesterton

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Chesterton Flights as Low as $58

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

Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 17 hours ago
$58
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 17 hours ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 1 day ago
Frontier Airlines
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, found 17 hours ago
$68
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Feb 25, priced at $68 found 17 hours ago
Frontier Airlines
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 17 hours ago
$68
Roundtrip
found 17 hours 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 17 hours ago
Spirit Airlines
Tue, Mar 25 - Tue, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $73 found 1 day ago
Spirit Airlines
Sat, Feb 1 - Mon, Feb 3
LGA
LaGuardia
ORD
O'Hare Intl.
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Feb 1 from LaGuardia to O'Hare Intl., returning Mon, Feb 3, priced at $86 found 1 day ago
Spirit Airlines
Wed, Feb 12 - Wed, Feb 19
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Feb 12 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Feb 19, priced at $116 found 1 day ago
Delta
Wed, Mar 19 - Wed, Mar 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Mar 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 19, priced at $134 found 1 day ago
United
Sat, Mar 8 - Tue, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Mar 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $137 found 2 hours ago
American Airlines
Sat, Mar 8 - Tue, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Mar 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $137 found 2 hours ago
Contour Airlines
Wed, Feb 12 - Thu, Feb 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day 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 1 day ago
Delta
Wed, Feb 19 - Tue, Feb 25
DAL
Love Field
ORD
O'Hare Intl.
$197 Roundtrip, found 17 hours ago
$197
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 19 from Love Field to O'Hare Intl., returning Tue, Feb 25, priced at $197 found 17 hours ago
Delta
Wed, Feb 19 - Tue, Feb 25
DAL
Love Field
MDW
Midway Intl.
$208 Roundtrip, found 17 hours ago
$208
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 19 from Love Field to Midway Intl., returning Tue, Feb 25, priced at $208 found 17 hours ago
Frontier Airlines
Thu, Jan 23 - Sun, Jan 26
LGA
LaGuardia
MDW
Midway Intl.
$237 Roundtrip, found 13 hours ago
$237
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Jan 23 from LaGuardia to Midway Intl., returning Sun, Jan 26, priced at $237 found 13 hours ago
Delta
Tue, May 27 - Sun, Jun 1
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$273 Roundtrip, found 6 days ago
$273
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 27 from Detroit Metropolitan Wayne County to Midway Intl., returning Sun, Jun 1, priced at $273 found 6 days ago
JetBlue Airways
Tue, Mar 25 - Tue, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Mar 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $292 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 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 $58, 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 $58 right now, why wait?

Chesterton Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$68

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 Jan 20 to Jan 21
$88
includes taxes & fees
Jan 20 - Jan 21
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)
"Property was generally fine. Breakfast was very limited, but worked for a single morning. Access to the site was problematic with road construction around the property and some challenges finding how to access the property late at night. Check in was late at night, and we did not have problems getting ..."

Reviewed on Jan 3, 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 $100 per night from Feb 2 to Feb 3
$100
includes taxes & fees
Feb 2 - Feb 3
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)
"Nice quiet overnight stop when traveling in January."

Reviewed on Jan 9, 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 Feb 2 to Feb 3
$112
includes taxes & fees
Feb 2 - Feb 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)
"Front desk was great easy checking took two minutes . After driving 14 hrs that was really nice . Room was inviting ."

Reviewed on Jan 17, 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 Jan 20 to Jan 21
$91
includes taxes & fees
Jan 20 - Jan 21
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! (789 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 $83 per night from Jan 21 to Jan 22
$83
includes taxes & fees
Jan 21 - Jan 22
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! (1,000 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 Jan 20 to Jan 21
$168
includes taxes & fees
Jan 20 - Jan 21
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes National Park and Brincka Cross ...
8.6/10 Excellent! (45 reviews)
Family event
"We could only stay one night but it was amazing will definitely recommend to others and will stay again when we travel to North West Indiana"

Reviewed on Dec 17, 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 $140 per night from Jan 20 to Jan 21
$140
includes taxes & fees
Jan 20 - Jan 21
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! (1,362 reviews)
One night getaway
"A one night getaway with my wife to relax and connect."

Reviewed on Jan 12, 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 Jan 20 to Jan 21
$115
includes taxes & fees
Jan 20 - Jan 21
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! (1,029 reviews)
"We had a nice stay. The staff was very nice!"

Reviewed on Jan 14, 2025

Four Winds Casino Resort – New Buffalo
See all 1,296 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.