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Rutland

$354+ Cheap flights from Illinois to Rutland (RUT)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RUT
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheap flight deals from Illinois to Rutland

Keep the following information in mind while searching for Illinois to Rutland flight deals. Data was last updated October 6, 2025.

Round-trip from

$354
(JetBlue)
From Illinois to Rutland
Search Deals

Find flight deals from Illinois to Rutland

Cheapest flights from Illinois to Rutland
Explore the most affordable flight options available from Illinois to Rutland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2025.

This lastminute.com deal was found by Cheapflights users on 10/5. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:20 amORD - RUT
1 stop22h 07mJetBlue
Wed 11/267:20 amRUT - ORD
1 stop13h 30mJetBlue
Deal found 10/5$426
This JetBlue deal was found by Cheapflights users on 10/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:08 amORD - RUT
1 stop7h 45mJetBlue
Fri 10/2411:22 amRUT - ORD
1 stop7h 56mJetBlue
Deal found 10/5$484
This JetBlue deal was found by Cheapflights users on 10/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:20 amORD - RUT
1 stop6h 33mJetBlue
Mon 11/1011:22 amRUT - ORD
1 stop7h 33mJetBlue
Deal found 10/5$489
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Wed 11/193:26 pmORD - RUT
2 stops18h 01mMultiple Airlines
Wed 11/267:20 amRUT - ORD
3 stops26h 57mMultiple Airlines
Deal found 10/5$578
This JetBlue deal was found by Cheapflights users on 10/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:08 amORD - RUT
1 stop7h 45mJetBlue
Fri 10/2411:22 amRUT - ORD
1 stop7h 56mJetBlue
Deal found 10/3$839

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 October 6, 2025.
Use the filters below to find and compare flights from Illinois to Rutland that are best for you.

Fly from

Illinois

Fly to

Rutland

Route

Depart

Return

Price

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 3/25

12:10 pm-6:53 pm

1 stop5h 43m

Rutland

Thu 3/26

11:22 am-5:31 pm

1 stop7h 09m

$354

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 11/19

11:20 am-10:27 am

1 stop22h 07m

Rutland

Wed 11/26

7:20 am-7:50 pm

1 stop13h 30m

$426

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 10/20

10:08 am-6:53 pm

1 stop7h 45m

Rutland

Fri 10/24

11:22 am-6:18 pm

1 stop7h 56m

$484

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 11/14

11:20 am-6:53 pm

1 stop6h 33m

Rutland

Sun 11/16

11:22 am-5:55 pm

1 stop7h 33m

$489

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 11/3

11:20 am-6:53 pm

1 stop6h 33m

Rutland

Mon 11/10

11:22 am-5:55 pm

1 stop7h 33m

$489

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 11/19

3:26 pm-10:27 am

2 stops18h 01m

Rutland

Wed 11/26

7:20 am-9:17 am

3 stops26h 57m

$578

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 10/17

10:08 am-6:53 pm

1 stop7h 45m

Rutland

Fri 10/24

11:22 am-6:18 pm

1 stop7h 56m

$839

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 10/13

10:08 am-7:05 pm

1 stop7h 57m

$642

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Best time to book a flight from Illinois to Rutland

Have a flexible travel schedule? Discover the best time to fly to Rutland from Illinois 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 Illinois to Rutland

What is the cheapest month to book a flight from Illinois to Rutland?

Currently, April is the cheapest month in which you can book a flight from Illinois to Rutland (average of $202). Flying from Illinois 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 Illinois 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 Illinois?

    For a flight from Illinois to Rutland, you will be flying into Rutland. Rutland (RUT) is just 5.9 mi from the center of the city.

  • How long is the flight from Illinois to Rutland?

    For as low as $354, JetBlue can have you in Rutland from Illinois in 5h 43m. The distance between Illinois and Rutland is about 765 mi.

  • Can I find deals for flights from Illinois to Rutland that include hotel bookings?

    Yes. In addition to deals on Illinois to Rutland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Rutland?

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

  • Can I find deals for business class flights from Illinois to Rutland?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Rutland?

    Currently, April is the cheapest month in which you can book a flight from Illinois to Rutland (average of $202). Flying from Illinois 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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