HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Rutland

$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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RUT
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Rutland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from O'Hare Intl to Rutland

Best flights from O'Hare Intl to Rutland
Discover carefully curated flight deals from O'Hare Intl to Rutland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 1, 2026.

This Priceline deal was found by Cheapflights users on 12/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/147:45 amORD - RUT
1 stop9h 46mMultiple Airlines
Sun 1/1811:19 amRUT - ORD
1 stop7h 24mMultiple Airlines
Deal found 12/30$364
This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 amORD - RUT
1 stop8h 07mMultiple Airlines
Sun 5/173:31 pmRUT - ORD
1 stop7h 05mMultiple Airlines
Deal found 12/29$374

Find 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 January 1, 2026.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$364
(Priceline)

One-way from

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

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 January 1, 2026.
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

Wed 1/14

7:45 am-6:31 pm

1 stop9h 46m

Rutland

Sun 1/18

11:19 am-5:43 pm

1 stop7h 24m

$364

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 5/14

6:00 am-3:07 pm

1 stop8h 07m

Rutland

Sun 5/17

3:31 pm-9:36 pm

1 stop7h 05m

$374

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 2/10

7:45 am-3:07 pm

1 stop6h 22m

$167

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 1/21

7:45 am-3:07 pm

1 stop6h 22m

$167

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 2/19

10:00 am-6:31 pm

1 stop7h 31m

$167

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 1/20

7:45 am-3:07 pm

1 stop6h 22m

$167

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 2/17

10:00 am-6:31 pm

1 stop7h 31m

$167

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

Thu 1/29

7:45 am-3:07 pm

1 stop6h 22m

$177

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 2/14

10:00 am-6:31 pm

1 stop7h 31m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 14 results
1
2
  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Rutland flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago O'Hare Intl Airport-Rutland flight deals on Cheapflights vs. Expedia 90-95% 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 Expedia the most. Expedia 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 $155). Flying from Chicago O'Hare Intl Airport to Rutland in February is currently the most expensive (average of $249). 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.

  • 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 $155). Flying from Chicago O'Hare Intl Airport to Rutland in February is currently the most expensive (average of $249). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.