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Orwell

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Orwell Flights as Low as $490

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

Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$490 Roundtrip, found 1 day ago
$490
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $490 found 1 day ago
Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$496 Roundtrip, found 1 day ago
$496
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $496 found 1 day ago
United
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$500 Roundtrip, found 1 day ago
$500
Roundtrip
found 1 day ago
Select United flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $500 found 1 day ago
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 1 day ago
$503
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $503 found 1 day ago
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$508 Roundtrip, found 1 day ago
$508
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $508 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $524 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $524 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$529 Roundtrip, found 1 day ago
$529
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $529 found 1 day ago
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$535 Roundtrip, found 1 day ago
$535
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $535 found 1 day ago
Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$540 Roundtrip, found 1 day ago
$540
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $540 found 1 day ago
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$545 Roundtrip, found 1 day ago
$545
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $545 found 1 day ago
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$550 Roundtrip, found 1 day ago
$550
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $550 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$560 Roundtrip, found 1 day ago
$560
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $560 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$560 Roundtrip, found 1 day ago
$560
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $560 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$570 Roundtrip, found 1 day ago
$570
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $570 found 1 day ago
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$570 Roundtrip, found 1 day ago
$570
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $570 found 1 day ago

Cheap Flights to Orwell

Fall in love at first flight with your vacation to Orwell 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 Orwell on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Orwell, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Orwell

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Orwell 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 GFL airport.

What is the cheapest month to fly to Orwell?

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 Orwell are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Orwell?

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 Orwell.

What airport is best to fly into Orwell?

When you’re planning your trip to Orwell, convenience is the name of the game. Luckily, Orwell Rutland Southern Vermont Regional Airport is nearby so you can deplane and get going on checking off everything on your Orwell must-do list.

How much are flights to Orwell?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Orwell on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $490, 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 Orwell?

The trick to saving a stack of cash on your flight to Orwell? 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 $490 right now, why wait?

Orwell Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$490

Last Minute Hotel Deals in Orwell

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
The price is $145 per night from Jan 26 to Jan 27
$145
includes taxes & fees
Jan 26 - Jan 27
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,005 reviews)
"nice"

Reviewed on Jan 21, 2025

Comfort Inn Rutland - Killington
Days Inn by Wyndham Rutland/Killington Area
Days Inn by Wyndham Rutland/Killington Area
2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
The price is $135 per night from Feb 2 to Feb 3
$135
includes taxes & fees
Feb 2 - Feb 3
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,002 reviews)
Enjoyable trip
"We had two pets that were with us and one was a service animals which the accommodation was well met,"

Reviewed on Jan 20, 2025

Days Inn by Wyndham Rutland/Killington Area
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-Killington
2.5 out of 5
5 Best Western Place, Rutland, VT
The price is $197 per night from Feb 2 to Feb 3
$197
includes taxes & fees
Feb 2 - Feb 3
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (999 reviews)
"The room was small and could use updating. However, it was clean and convenient. The breakfast in the morning was great before skiing. Friendly staff"

Reviewed on Jan 23, 2025

Best Western Inn & Suites Rutland-Killington
Hampton Inn Rutland
Hampton Inn Rutland
2.5 out of 5
47 Farrell Rd, Rutland, VT
The price is $223 per night from Feb 2 to Feb 3
$223
includes taxes & fees
Feb 2 - Feb 3
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (885 reviews)
Can’t go wrong here. Excellent
"Extremely clean and pleasant. I thought it was expensive for a Hampton Inn but it’s winter in a ski area so it’s market rate for that. The free breakfast was good. The dining area has a gas fireplace and tv. Very comfortable. They spend a lot of time every day making sure they clean up water and ..."

Reviewed on Jan 14, 2025

Hampton Inn Rutland
Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
The price is $164 per night from Feb 16 to Feb 17
$164
includes taxes & fees
Feb 16 - Feb 17
Book a stay at this historic hotel in Middlebury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,001 reviews)
"Very gracious accommodations. Old world charm."

Reviewed on Jan 20, 2025

Middlebury Inn
Brandon Inn
Brandon Inn
3 out of 5
20 Park Street, Brandon, VT
The price is $166 per night from Jan 26 to Jan 27
$166
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3-star hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (410 reviews)
"Quiet and comfortable"

Reviewed on Jan 24, 2025

Brandon Inn
Emrose Luxury Cabins
Emrose Luxury Cabins
2 out of 5
1246 Franklin Street, Brandon, VT
The price is $220 per night from Jan 26 to Jan 27
$220
includes taxes & fees
Jan 26 - Jan 27
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are ...
9.8/10 Exceptional! (15 reviews)
"The cabin was perfect! I really love the modern indoor decoration here:) And the cabin even has a small kitchen where we could cook! It is so nice staying here and it is also close to Killington ski area, and we really had a good time here. I’ll definitely get back if I go ski here again!"

Reviewed on Jan 20, 2025

Emrose Luxury Cabins
Lake Bomoseen Lodge
Lake Bomoseen Lodge
3.5 out of 5
2551 Vermont 30N, Bomoseen, VT
The price is $174 per night from Jan 26 to Jan 27
$174
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3.5-star beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff ...
9.2/10 Wonderful! (725 reviews)
"The room is super spacious and clean. We had a good stay. Will visit again!"

Reviewed on Jan 23, 2025

Lake Bomoseen Lodge
See all 520 properties in Orwell
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.