$172 Cheap Flights from Chicago (ORD) to Rutland (RUT)

View $172 flight on Tue, Mar 24, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Rutland, VT (RUT-Rutland Southern Vermont Regional)

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Cheap Flights from Chicago to Rutland (ORD-RUT)

Prices were available within the past 7 days and start at $172 for one-way flights and $329 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Thu, Nov 27 - Tue, Dec 2
ORD
Chicago
RUT
Rutland
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Nov 27 from Chicago to Rutland, returning Tue, Dec 2, priced at $329 found 2 days ago
JetBlue Airways
Wed, Nov 26 - Tue, Dec 2
ORD
Chicago
RUT
Rutland
$344 Roundtrip, found 2 days ago
$344
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Nov 26 from Chicago to Rutland, returning Tue, Dec 2, priced at $344 found 2 days ago
Delta
Thu, Nov 27 - Wed, Dec 3
ORD
Chicago
RUT
Rutland
$344 Roundtrip, found 2 days ago
$344
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 27 from Chicago to Rutland, returning Wed, Dec 3, priced at $344 found 2 days ago
JetBlue Airways
Fri, Jan 23 - Sun, Jan 25
ORD
Chicago
RUT
Rutland
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Jan 23 from Chicago to Rutland, returning Sun, Jan 25, priced at $349 found 1 day ago
JetBlue Airways
Mon, Nov 17 - Sat, Nov 22
ORD
Chicago
RUT
Rutland
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Nov 17 from Chicago to Rutland, returning Sat, Nov 22, priced at $352 found 1 day ago
JetBlue Airways
Sat, Jan 24 - Fri, Jan 30
ORD
Chicago
RUT
Rutland
$354 Roundtrip, found 1 day ago
$354
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jan 24 from Chicago to Rutland, returning Fri, Jan 30, priced at $354 found 1 day ago
American Airlines
Thu, Feb 26 - Sun, Mar 1
ORD
Chicago
RUT
Rutland
$354 Roundtrip, found 5 days ago
$354
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Feb 26 from Chicago to Rutland, returning Sun, Mar 1, priced at $354 found 5 days ago
JetBlue Airways
Thu, Dec 25 - Wed, Dec 31
ORD
Chicago
RUT
Rutland
$356 Roundtrip, found 3 days ago
$356
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Dec 25 from Chicago to Rutland, returning Wed, Dec 31, priced at $356 found 3 days ago
JetBlue Airways
Tue, Feb 24 - Sat, Feb 28
ORD
Chicago
RUT
Rutland
$357 Roundtrip, found 5 days ago
$357
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Feb 24 from Chicago to Rutland, returning Sat, Feb 28, priced at $357 found 5 days ago
JetBlue Airways
Mon, Jan 19 - Tue, Jan 20
ORD
Chicago
RUT
Rutland
$358 Roundtrip, found 6 days ago
$358
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Jan 19 from Chicago to Rutland, returning Tue, Jan 20, priced at $358 found 6 days ago

Alternative airports near Rutland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Rutland Southern Vermont Regional RUT. Cheapest and Closest option available. Average driving time to city center is 10 minutes. Flights from $495
RUT
Rutland Southern Vermont Regional
CheapestClosest
Average driving time to city center10 min
Flights from $495

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT) cost?
Snag a cheap one-way flight from $172 or cheap return flight from $329 from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT)?
The cheapest month to fly from ORD to RUT is November, when demand is low. Off-peak months are typically when better flight deals are available between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ORD to RUT flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT)?
There are no daily nonstop flights departing from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to RUT?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT)?
Opt for a flight from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Rutland from O'Hare Intl. Airport (ORD)?
Burlington Intl. Airport (BTV) is the only airport in Rutland with direct flights from O'Hare Intl. Airport (ORD). Browse your options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT) last-minute?
Holding off until right before your break to book a ticket from ORD to RUT often results in higher prices. While you might find some last-minute offers, they're not always guaranteed. Keep your travel plans flexible to boost your chances of scoring a bargain.
Is it cheaper to book an ORD to RUT flight and hotel package?
You'll typically save money by securing an ORD to RUT flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've selected your ideal flights and accommodations, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Rutland Southern Vermont Regional Airport (RUT)?
In most instances, you're able to reschedule or cancel your ORD to RUT flight. However, additional charges may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Rutland Southern Vermont Regional
Airlines serving
JetBlue Airways
Roundtrip price
$328
Distance
765 mi

Book with confidence

Chicago to Rutland Flights

The cheapest times to fly from Chicago to Rutland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Rutland are during the month of November. You can find some of the cheapest flights from Chicago to Rutland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Rutland

Sunday is one of the best days to book for cheap flights from Chicago to Rutland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Rutland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Rutland in 2025. You can also book with separate airlines for your outbound and return journeys, from $172 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Rutland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Rutland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Rutland Flights

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