Cheap Flights To Chesterton 2025

Chesterton Flights as Low as $108

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jun 24 - Tue, Jul 1
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Jul 1, priced at $108 just found
Frontier Airlines
Tue, Jun 24 - Mon, Jun 30
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Jun 30, priced at $110 just found
Frontier Airlines
Fri, Jun 27 - Mon, Jun 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jun 27 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jun 30, priced at $112 just found
Frontier Airlines
Tue, Jun 24 - Sat, Jun 28
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Jun 28, priced at $116 just found
Frontier Airlines
Thu, May 29 - Sun, Jun 1
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 29 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Jun 1, priced at $122 found 1 day ago
Spirit Airlines
Wed, May 14 - Mon, May 19
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 22 hours ago
$153
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Wed, May 14 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, May 19, priced at $153 found 22 hours ago
Spirit Airlines
Wed, May 7 - Tue, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 7 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 13, priced at $178 found 1 day ago
American Airlines
Sat, Jun 14 - Sat, Jul 5
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 5 days ago
$188
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jun 14 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $188 found 5 days ago
Delta
Tue, May 20 - Wed, May 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 22 hours ago
$197
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, May 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, May 21, priced at $197 found 22 hours ago
United
Fri, Jun 27 - Mon, Jun 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select United flight, departing Fri, Jun 27 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jun 30, priced at $199 just found
Delta
Sat, Jun 14 - Sat, Jul 5
DAL
Love Field
ORD
O'Hare Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jun 14 from Love Field to O'Hare Intl., returning Sat, Jul 5, priced at $208 found 5 days ago
Delta
Sat, Aug 9 - Sat, Aug 9
DAL
Love Field
MDW
Midway Intl.
$211 Roundtrip, found 6 days ago
$211
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 9 from Love Field to Midway Intl., returning Sat, Aug 9, priced at $211 found 6 days ago
Delta
Mon, Jun 2 - Mon, Jun 2
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jun 2 from Charlotte-Douglas Intl. to Midway Intl., returning Mon, Jun 2, priced at $273 found 1 day ago
Contour Airlines
Fri, Jun 27 - Mon, Jun 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$297 Roundtrip, just found
$297
Roundtrip
just found
Select Contour Airlines flight, departing Fri, Jun 27 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jun 30, priced at $297 just found
Delta
Thu, May 8 - Tue, May 13
IAH
George Bush Intercontinental
MDW
Midway Intl.
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 8 from George Bush Intercontinental to Midway Intl., returning Tue, May 13, priced at $323 found 1 day ago
United
Sat, Jul 12 - Mon, Jul 14
CRP
Corpus Christi Intl.
ORD
O'Hare Intl.
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jul 12 from Corpus Christi Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $349 found 1 day ago

Flight Travel Guide to Chesterton

Do you have a travel itch? Maybe it's time to book a flight to Chesterton. And with the AARP Travel Center Powered by Expedia®, you are in good hands. AARP Travel combines their members-only discount with the best rates from Expedia, so members get the best price in travel, guaranteed. As an AARP member, you'll get exclusive rates on car rentals and hotels, and won't pay booking fees on flights.

Whether it's a backpacking adventure, ski escape, weekend getaway, tropical destination or another trip you're dreaming of–we'll help you get there (without breaking the bank).

Transportation at the Airport

Once you have got your flight scheduled to Chesterton with AARP Travel, you might want to book a vehicle so you can get around on your own. You can book Chesterton rental cars under our cars tab and get into the driver's seat right when you step out of the airport. For more information, check out the Chesterton Car Rentals Guide.

Chesterton Activities

If you aren't sure where to start, we can help you with that too. Not to worry—there's plenty to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in Chesterton, make sure you look at our "Things to Do in Chesterton" page for excursions and activities for the whole clan.

Book Your Hotel in Chesterton

Chesterton has hotel options in the area, so you will have no trouble finding a place to stay close to all the things you want to see. If you need to stay close to the airport, or another attraction in Chesterton, check out our hotel listings page. No matter where you stay, just remember that you'll get the best for your trip when you book with us.

Book Your Chesterton Trip Today

We know that you want to focus more on the fun stuff and less on the airfare prices, so we provide travel arrangements that fall within your budget. There is no better time than now to start booking your next trip. Book one of our flights today.