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Cheap flights from Illinois to Rutland from $252

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Rutland departing on 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Illinois to Rutland

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
6:45 am - 6:53 pmORD-RUT
11h 08m1 stop
JetBlue Logo
7:20 am - 5:44 pmRUT-ORD
11h 24m1 stop
$339JetBlue
Find Deal
Mon, Jan 12 - Thu, Jan 15
JetBlue Logo
8:45 am - 6:53 pmORD-RUT
9h 08m2 stops
JetBlue Logo
7:20 am - 5:44 pmRUT-ORD
11h 24m1 stop
$352JetBlue
Find Deal
Mon, Jan 12 - Thu, Jan 15
JetBlue Logo
7:45 am - 2:51 pmORD-RUT
6h 06m1 stop
JetBlue Logo
11:22 am - 5:44 pmRUT-ORD
7h 22m1 stop
$354JetBlue
Find Deal
Sat, Jan 24 - Fri, Jan 30
JetBlue Logo
11:25 am - 6:53 pmORD-RUT
6h 28m1 stop
JetBlue Logo
11:22 am - 7:43 pmRUT-ORD
9h 21m1 stop
$369JetBlue
Find Deal
Sat, Dec 6 - Mon, Dec 8
JetBlue Logo
6:45 am - 6:53 pmORD-RUT
11h 08m1 stop
JetBlue Logo
7:20 am - 5:44 pmRUT-ORD
11h 24m1 stop
$389JetBlue
Find Deal
Mon, Jan 12 - Fri, Jan 16
JetBlue Logo
6:45 am - 6:53 pmORD-RUT
11h 08m1 stop
JetBlue Logo
7:20 am - 7:45 pmRUT-ORD
13h 25m2 stops
$393JetBlue
Find Deal
Mon, Jan 12 - Fri, Jan 16
Multiple Airlines Logo
1:57 pm - 10:27 amORD-RUT
19h 30m1 stop
Multiple Airlines Logo
11:22 am - 8:25 pmRUT-ORD
10h 03m1 stop
$394Multiple Airlines
Find Deal
Sat, Feb 14 - Fri, Feb 20
Multiple Airlines Logo
6:16 pm - 2:51 pmORD-RUT
19h 35m1 stop
Multiple Airlines Logo
7:20 am - 4:56 pmRUT-ORD
10h 36m2 stops
$404Multiple Airlines
Find Deal
Sat, Jan 24 - Fri, Jan 30
Multiple Airlines Logo
7:10 am - 6:53 pmORD-RUT
10h 43m2 stops
Multiple Airlines Logo
4:01 pm - 11:39 pmRUT-ORD
8h 38m2 stops
$414Multiple Airlines
Find Deal
Mon, Jan 12 - Fri, Jan 16
JetBlue Logo
12:10 pm - 6:53 pmORD-RUT
5h 43m1 stop
JetBlue Logo
7:20 am - 11:24 amRUT-ORD
5h 04m1 stop
$419JetBlue
Find Deal
Wed, Mar 25 - Thu, Mar 26

JetBlue flights from Illinois to Rutland

Our best JetBlue deals on Illinois to Rutland flight tickets
JetBlue
Jan 12
ORD6:45 amChicago O'Hare Intl
11h 08m
1 stop
RUT6:53 pmRutland
Jan 15
RUT7:20 amRutland
11h 24m
1 stop
ORD5:44 pmChicago O'Hare Intl
$339
Find similar
JetBlue
Jan 12
ORD8:45 amChicago O'Hare Intl
9h 08m
2 stops
RUT6:53 pmRutland
Jan 15
RUT7:20 amRutland
11h 24m
1 stop
ORD5:44 pmChicago O'Hare Intl
$352
Find similar
JetBlue
Jan 24
ORD7:45 amChicago O'Hare Intl
6h 06m
1 stop
RUT2:51 pmRutland
Jan 30
RUT11:22 amRutland
7h 22m
1 stop
ORD5:44 pmChicago O'Hare Intl
$354
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated November 5, 2025.
Use the filters below to find and compare flights from Illinois to Rutland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 1/12

6:45 am-6:53 pm

1 stop11h 08m

Rutland

Thu 1/15

7:20 am-5:44 pm

1 stop11h 24m

$339

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 1/12

8:45 am-6:53 pm

2 stops9h 08m

Rutland

Thu 1/15

7:20 am-5:44 pm

1 stop11h 24m

$352

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 1/24

7:45 am-2:51 pm

1 stop6h 06m

Rutland

Fri 1/30

11:22 am-5:44 pm

1 stop7h 22m

$354

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 12/6

11:25 am-6:53 pm

1 stop6h 28m

Rutland

Mon 12/8

11:22 am-7:43 pm

1 stop9h 21m

$369

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 1/12

6:45 am-6:53 pm

1 stop11h 08m

Rutland

Fri 1/16

7:20 am-5:44 pm

1 stop11h 24m

$389

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 1/12

6:45 am-6:53 pm

1 stop11h 08m

Rutland

Fri 1/16

7:20 am-7:45 pm

2 stops13h 25m

$393

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 2/14

1:57 pm-10:27 am

1 stop19h 30m

Rutland

Fri 2/20

11:22 am-8:25 pm

1 stop10h 03m

$394

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Sat 1/24

6:16 pm-2:51 pm

1 stop19h 35m

Rutland

Fri 1/30

7:20 am-4:56 pm

2 stops10h 36m

$404

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Mon 1/12

7:10 am-6:53 pm

2 stops10h 43m

Rutland

Fri 1/16

4:01 pm-11:39 pm

2 stops8h 38m

$414

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 3/25

12:10 pm-6:53 pm

1 stop5h 43m

Rutland

Thu 3/26

7:20 am-11:24 am

1 stop5h 04m

$419

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Rutland from

How to get the cheapest flight ticket from Illinois to Rutland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Illinois to Rutland?

JetBlue is the most popular carrier operating from Illinois to Rutland

What airlines fly to Rutland?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Rutland from Illinois according to our data. United Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Rutland. Keep in mind that there are 3 different airlines that fly to Rutland on a routine basis, so you have a few additional options to choose from.

Cheap Illinois to Rutland flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Rutland

Direct flights

None
There are no direct flights from Illinois to Rutland. There are no popular flight routes from Illinois to Rutland.
Search flight deals

  • When did momondo last update prices for flights from Illinois to Rutland Airport?

    Prices for flights from Illinois to Rutland Airport were last updated today.

  • How old do you have to be to fly from Illinois to Rutland Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Rutland Airport.

  • What documentation or ID do you need to fly to Rutland Airport?

    The travel and health documents required for your trip to Rutland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Rutland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Rutland?

Book flights to Rutland if you plan to visit one of these locations
Lake George
Killington
Ludlow
Stratton
Ticonderoga
Dover
Londonderry
Chester
Dorset

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Rutland?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Rutland. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Illinois to Rutland with flexible booking policies on momondo?

Flights from Illinois to Rutland with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Illinois to Rutland?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Rutland.

I’m not ready to book a flight from Illinois to Rutland right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Rutland from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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