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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, May 12 - Wed, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$58 Roundtrip, found 8 hours ago
$58
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 13, priced at $58 found 8 hours ago
Frontier Airlines
Tue, May 12 - Wed, May 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 16 hours ago
$58
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Wed, May 13, priced at $58 found 16 hours ago
Frontier Airlines
Fri, Jul 3 - Sat, Jul 4
MCO
Orlando Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 7 hours ago
$88
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Jul 3 from Orlando Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $88 found 7 hours ago
Spirit Airlines
Tue, May 12 - Tue, May 12
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 12, priced at $89 found 1 day ago
Frontier Airlines
Tue, May 5 - Mon, May 18
MCO
Orlando Intl.
MDW
Midway Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Orlando Intl. to Midway Intl., returning Mon, May 18, priced at $159 found 6 days ago
United
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select United flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $163 found 1 day ago
American Airlines
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $163 found 1 day ago
Frontier Airlines
Thu, May 28 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 28 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $168 found 2 days ago
Frontier Airlines
Wed, May 6 - Tue, May 12
DEN
Denver Intl.
MDW
Midway Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 6 from Denver Intl. to Midway Intl., returning Tue, May 12, priced at $186 found 3 days ago
Frontier Airlines
Mon, May 11 - Tue, May 12
IAH
George Bush Intercontinental
MDW
Midway Intl.
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, May 11 from George Bush Intercontinental to Midway Intl., returning Tue, May 12, priced at $191 found 5 days ago
Delta
Wed, Jul 1 - Wed, Jul 1
MCO
Orlando Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Jul 1 from Orlando Intl. to O'Hare Intl., returning Wed, Jul 1, priced at $197 found 4 hours ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
RFD
Greater Rockford
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Greater Rockford, returning Thu, May 28, priced at $219 found 1 day ago
Frontier Airlines
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Midway Intl., returning Thu, May 28, priced at $236 found 1 day ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$281 Roundtrip, found 2 days ago
$281
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $281 found 2 days ago
American Airlines
Fri, May 1 - Tue, May 5
DEN
Denver Intl.
RFD
Greater Rockford
$360 Roundtrip, found 9 hours ago
$360
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, May 1 from Denver Intl. to Greater Rockford, returning Tue, May 5, priced at $360 found 9 hours ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$361 Roundtrip, found 6 days ago
$361
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $361 found 6 days 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 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
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$57

Last Minute Hotel Deals in Chesterton

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 ...
8.8/10 Excellent! (1,000 reviews)
The property is pretty and very clean. We used the fitness room, but not the pool. Both were clean and quiet. We would stay there again.

Reviewed on Apr 20, 2026

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Spring House 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 ...
8.6/10 Excellent! (1,002 reviews)
This is a great spot, so peaceful to wake up in the morning overlooking the lake and listening to the water fowl. Great value for the dollar.

Reviewed on Apr 23, 2026

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Best Western Indian Oak
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! (1,001 reviews)
Nice pleasant place to stay, fun to see and feed the geese, fish and turtles!!

Reviewed on Apr 24, 2026

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Waterbird Lakeside Inn
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! (1,000 reviews)
On site restaurant and bar were convenient and very nice. Walkable to restaurants. Very close to Indiana Dunes. Good WiFi. Clean. Hot tub and pool missed the mark in my opinion. Pool was rather chilly and hot tub doesn’t have bubbles. Maintenance said the tub is a spa so doesn’t have to.

Reviewed on Apr 21, 2026

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Hilton Garden Inn Chesterton
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! (1,000 reviews)
The room ac kept turning on and off every few minutes and didn't cool the room down. There is a main road right next to the hotel and an interstate highway just beyond that and our room faced them. I'm a lite sleeper and the noise from traffic kept me up most of the night. The fire alarm for the ...

Reviewed on Apr 1, 2026

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Comfort Inn & Suites Porter near Indiana Dunes
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive Michigan City IN
Book a stay at this 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 ...
8.4/10 Very Good! (2,030 reviews)
Room and casino were great, was surprised how little the smoking affected us. Pool was closed and we were looking forward to the hot tubs. There wasn't an indication this was going to happen when I booked. I doubt it was a surprise closure.

Reviewed on Apr 24, 2026

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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
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! (1,837 reviews)
Excellent hotel with one exception: our non-smoking room smelled of smoke. That may be the risk involved in staying at a casino hotel. Otherwise, everything was top notch.

Reviewed on Apr 24, 2026

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Four Winds Casino Resort – New Buffalo
FairBridge Inn Express Merrillville

FairBridge Inn Express Merrillville

2 out of 5
8250 Louisiana Street Merrillville IN
Stay at this motel in Merrillville. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (601 reviews)
Quiet and spacious

Reviewed on Apr 18, 2026

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FairBridge Inn Express Merrillville
See all 1,445 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.