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$167+ Cheap flights from O'Hare Intl (ORD) to Rutland (RUT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RUT
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Find flight deals from O'Hare Intl to Rutland

Cheapest flights from O'Hare Intl to Rutland
Explore the most affordable flight options available from O'Hare Intl to Rutland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 18, 2025.

This Mytrip deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:43 pmORD - RUT
2 stops17h 44mMultiple Airlines
Sat 12/67:20 amRUT - ORD
2 stops15h 28mMultiple Airlines
Deal found 11/17$395

Cheap flight deals from O'Hare Intl to Rutland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Rutland (RUT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$349
(JetBlue)

One-way from

$167
(JetBlue)
Provider with most accurate pricing for Chicago O'Hare Intl-Rutland flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Rutland flights.
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From Chicago O'Hare Intl to Rutland
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One-way flight from Chicago O'Hare Intl to Rutland
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Rutland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Rutland that are best for you.

Fly from

O'Hare Intl

Fly to

Rutland

Route

Depart

Return

Price

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sun 1/25

7:45 am-3:07 pm

1 stop6h 22m

Rutland

Wed 1/28

11:19 am-5:44 pm

1 stop7h 25m

$349

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sun 1/25

7:45 am-3:07 pm

1 stop6h 22m

Rutland

Fri 1/30

11:19 am-5:44 pm

1 stop7h 25m

$359

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 12/2

3:43 pm-10:27 am

2 stops17h 44m

Rutland

Sat 12/6

7:20 am-10:11 pm

3 stops15h 51m

$422

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 12/15

11:25 am-6:31 pm

1 stop6h 06m

Rutland

Mon 12/22

7:15 am-6:46 pm

1 stop12h 31m

$559

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 2/14

10:00 am-6:31 pm

1 stop7h 31m

$167

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 2/10

7:45 am-3:07 pm

1 stop6h 22m

$177

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 2/12

10:00 am-6:31 pm

1 stop7h 31m

$177

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 2/11

7:45 am-3:07 pm

1 stop6h 22m

$177

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 2/9

7:45 am-3:07 pm

1 stop6h 22m

$177

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sun 2/8

7:45 am-3:07 pm

1 stop6h 22m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Compare providers for flights from O'Hare Intl to Rutland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Rutland in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Rutland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Rutland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Rutland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Rutland flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Rutland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Rutland

Have a flexible travel schedule? Discover the best time to fly to Rutland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Rutland

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Rutland?

Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Rutland (average of $160). Flying from Chicago O'Hare Intl Airport to Rutland in February is currently the most expensive (average of $279). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Rutland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Rutland from Chicago O'Hare Intl?

    Located just 5.9 mi from the city center, Rutland is the airport most travelers will use when flying to Rutland from Chicago O'Hare Intl. Booking flights from Chicago O'Hare Intl to Rutland (RUT) should be relatively easy as there are 0 daily inbound flights from Chicago O'Hare Intl from 0 different airlines.

  • How long is the flight from Chicago O'Hare Intl Airport to Rutland?

    There are many flights that can get you from Chicago O'Hare Intl Airport to Rutland in 6h 22m. Fly via JetBlue to get the fastest option. Airlines will cover a distance of 765 mi.

  • Can I find deals for flights from O'Hare Intl to Rutland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Rutland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Rutland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Rutland.

  • Can I find deals for business class flights from O'Hare Intl to Rutland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Rutland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Rutland?

    Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Rutland (average of $160). Flying from Chicago O'Hare Intl Airport to Rutland in February is currently the most expensive (average of $279). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Rutland?

Book flights to Rutland if you plan to visit one of these locations
Lake George
Killington

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