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$288+ Cheap flights from Illinois 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RUT
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap 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 February 5, 2026.

This Priceline deal was found by Cheapflights users on 2/4. 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.
Sun 3/110:00 am
ORD
-
RUT
1 stop7h 31m
Multiple Airlines
Sat 3/73:31 pm
RUT
-
ORD
2 stops8h 29m
Multiple Airlines
Deal found 2/4$364
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Fri 2/1310:44 am
ORD
-
RUT
2 stops22h 34m
Multiple Airlines
Mon 2/1611:19 am
RUT
-
ORD
2 stops23h 20m
Multiple Airlines
Deal found 2/4$737

Find flight deals from Illinois to Rutland

Keep the following information in mind while searching for Illinois to Rutland flight deals. Data was last updated February 5, 2026.

Round-trip from

$364
(Priceline)

One-way from

$288
(Kiwi.com)
From Illinois to Rutland
Search Deals
One-way flight from Illinois to Rutland
Search Deals

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 February 5, 2026.
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

Sun 3/1

10:00 am-6:31 pm

1 stop7h 31m

Rutland

Sat 3/7

3:31 pm-11:00 pm

2 stops8h 29m

$364

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 2/21

4:43 pm-3:07 pm

3 stops45h 24m

$288

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 2/21

10:00 am-6:31 pm

1 stop7h 31m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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, December is the cheapest month in which you can book a flight from Illinois to Rutland (average of $151). Flying from Illinois to Rutland in July is currently the most expensive (average of $246). 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.

  • 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, December is the cheapest month in which you can book a flight from Illinois to Rutland (average of $151). Flying from Illinois to Rutland in July is currently the most expensive (average of $246). 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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