Search Cheap Flights to
Chesterton

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chesterton Flights as Low as $78

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

Frontier Airlines
Thu, Aug 6 - Mon, Aug 24
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Aug 24, priced at $78 found 1 day ago
Frontier Airlines
Thu, Sep 24 - Sun, Sep 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$162 Roundtrip, found 4 hours ago
$162
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, Sep 27, priced at $162 found 4 hours ago
Bargain Flight
Fri, Sep 25 - Sun, Sep 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Sep 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Sep 27, priced at $167 found 2 days ago
Bargain Flight
Sun, Aug 2 - Wed, Aug 5
BNA
Nashville Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 2 hours ago
$183
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Sun, Aug 2 from Nashville Intl. to O'Hare Intl., returning Wed, Aug 5, priced at $183 found 2 hours ago
Delta
Tue, Aug 25 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Aug 25, priced at $226 found 6 days ago
Contour Airlines
Sun, Aug 2 - Wed, Aug 5
BNA
Nashville Intl.
ORD
O'Hare Intl.
$235 Roundtrip, found 2 hours ago
$235
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Sun, Aug 2 from Nashville Intl. to O'Hare Intl., returning Wed, Aug 5, priced at $235 found 2 hours ago
American Airlines
Thu, Sep 3 - Sun, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Sep 3 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $240 found 2 days ago
Delta
Tue, Aug 18 - Sat, Sep 5
BNA
Nashville Intl.
MDW
Midway Intl.
$252 Roundtrip, found 22 hours ago
$252
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Aug 18 from Nashville Intl. to Midway Intl., returning Sat, Sep 5, priced at $252 found 22 hours ago
JetBlue Airways
Tue, Aug 18 - Sun, Aug 30
BNA
Nashville Intl.
ORD
O'Hare Intl.
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Nashville Intl. to O'Hare Intl., returning Sun, Aug 30, priced at $253 found 1 day ago
Viva
Wed, Oct 21 - Sat, Nov 7
GDL
Don Miguel Hidalgo y Costilla Intl.
ORD
O'Hare Intl.
$342 Roundtrip, found 1 day ago
$342
Roundtrip
found 1 day ago
Select Viva flight, departing Wed, Oct 21 from Don Miguel Hidalgo y Costilla Intl. to O'Hare Intl., returning Sat, Nov 7, priced at $342 found 1 day ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$361 Roundtrip, found 3 days ago
$361
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $361 found 3 days ago
American Airlines
Thu, Jul 30 - Sat, Aug 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$398 Roundtrip, found 2 days ago
$398
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jul 30 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Aug 1, priced at $398 found 2 days ago
Delta
Wed, Jan 27 - Sat, Feb 13
HYD
Rajiv Gandhi Intl.
ORD
O'Hare Intl.
$939 Roundtrip, found 1 day ago
$939
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 27 from Rajiv Gandhi Intl. to O'Hare Intl., returning Sat, Feb 13, priced at $939 found 1 day ago
British Airways
Wed, Jan 20 - Mon, Feb 8
HYD
Rajiv Gandhi Intl.
ORD
O'Hare Intl.
$948 Roundtrip, found 1 day ago
$948
Roundtrip
found 1 day ago
Select British Airways flight, departing Wed, Jan 20 from Rajiv Gandhi Intl. to O'Hare Intl., returning Mon, Feb 8, priced at $948 found 1 day ago
Air Canada
Tue, Dec 22 - Fri, Jan 8
HYD
Rajiv Gandhi Intl.
ORD
O'Hare Intl.
$967 Roundtrip, found 1 day ago
$967
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Dec 22 from Rajiv Gandhi Intl. to O'Hare Intl., returning Fri, Jan 8, priced at $967 found 1 day ago
Lufthansa
Sun, Dec 20 - Wed, Jan 6
HYD
Rajiv Gandhi Intl.
ORD
O'Hare Intl.
$974 Roundtrip, found 1 day ago
$974
Roundtrip
found 1 day ago
Select Lufthansa flight, departing Sun, Dec 20 from Rajiv Gandhi Intl. to O'Hare Intl., returning Wed, Jan 6, priced at $974 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 August, 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 14 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 $78, 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 $78 right now, why wait?

Chesterton Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$78

Last Minute Hotel Deals in Chesterton

Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
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. ...
8.2/10 Very Good! (1,008 reviews)
"The view from the balcony was great. However, the room was not totally clean. The sheets were clean, the comforter had a obvious blood stain on it, not enough washcloths, smoke on bathroom ceiling,mirror by entry door was not completely mounted, base of the beds were dirty and no staff available, ..."

Reviewed on Jul 19, 2026

Get rates
Waterbird Lakeside Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Get rates
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
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! (1,003 reviews)
"A very nice hotel. I honestly compare it to a Marriott from the breakfast to the modern updated rooms. Other than the older carpet all was great."

Reviewed on Jul 20, 2026

Get rates
Comfort Inn & Suites Porter near Indiana Dunes
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
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 ...
9/10 Wonderful! (1,008 reviews)
"The room was clean but dated."

Reviewed on Jul 21, 2026

Get rates
Spring House Inn
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 out of 5
418 Council Road Chesterton IN
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! (780 reviews)
"Staff was friendly and helpful. Room was clean. Perfect location, short drive to Indiana Dunes beach."

Reviewed on Jul 21, 2026

Get rates
Quality Inn Chesterton near Indiana Dunes National Park I-94
Furness Mansion

Furness Mansion

2 out of 5
1491 N Furnleigh Ln Chesterton IN
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Indiana Dunes State Park and Indiana Dunes National ...
8.8/10 Excellent! (77 reviews)
"This historic mansion has been completely updated. Thoughtful amenities were included, for example there’s a soda/snack station at the entry for a low fee. Our room was missing a hairdryer and they had run out of body wash - but we had our own so it didn’t create any issues. Having use of the laundry ..."

Reviewed on Jul 21, 2026

Get rates
Furness Mansion
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.8/10 Excellent! (1,002 reviews)
"The good… The hotel and the room were clean, as they should be. Everything else… Front desk gentleman was not particularly friendly or sociable. We needed extra blankets for my son who was sleeping on the pull out couch/bed since there was only one thin blanket and a sheet. He acted like it was a ..."

Reviewed on Jul 20, 2026

Get rates
Hilton Garden Inn Chesterton
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road New Buffalo MI
Book a stay at this business-friendly hotel in New Buffalo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (2,044 reviews)
"Staff at the steakhouse were rude, especially the hostess. Cassino was not very clean. We valet'd our car but it sat out in front of the cassino all night and was never valet'd. Never will stay at your casino in the future."

Reviewed on Jul 21, 2026

Get rates
Four Winds Casino Resort – New Buffalo
See all 1,450 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.