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Cheap flights from Chicago to Rutland from $228

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to Rutland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:38 am - 10:29 amORD  Chicago O'Hare Intl-RUT Rutland
23h 51m1 stop Boston Logan Intl
Multiple Airlines Logo
11:37 am - 7:14 pmRUT  Rutland-ORD Chicago O'Hare Intl
8h 37m1 stop Boston Logan Intl
$456Multiple Airlines
Wed, Oct 14 - Wed, Oct 21
Multiple Airlines Logo
7:30 am - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
6h 21m1 stop Boston Logan Intl
Multiple Airlines Logo
7:15 am - 2:26 pmRUT  Rutland-ORD Chicago O'Hare Intl
8h 11m2 stops Boston Logan Intl Washington, D.C. Dulles Intl
$476Multiple Airlines
Wed, Oct 14 - Wed, Oct 21
Multiple Airlines Logo
6:00 am - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
7h 51m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
7:15 am - 2:26 pmRUT  Rutland-ORD Chicago O'Hare Intl
8h 11m2 stops Boston Logan Intl Washington, D.C. Dulles Intl
$486Multiple Airlines
Wed, Oct 14 - Wed, Oct 21
Multiple Airlines Logo
6:59 am - 7:00 pmORD  Chicago O'Hare Intl-RUT Rutland
11h 01m1 stop Boston Logan Intl
Multiple Airlines Logo
11:37 am - 8:00 amRUT  Rutland-ORD Chicago O'Hare Intl
21h 23m1 stop Boston Logan Intl
$499Multiple Airlines
Wed, Nov 18 - Wed, Nov 25
Multiple Airlines Logo
5:00 am - 7:00 pmORD  Chicago O'Hare Intl-RUT Rutland
13h 00m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
11:37 am - 9:34 amRUT  Rutland-ORD Chicago O'Hare Intl
22h 57m1 stop Boston Logan Intl
$509Multiple Airlines
Wed, Nov 18 - Wed, Nov 25
Multiple Airlines Logo
7:55 pm - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
17h 56m1 stop Boston Logan Intl
Multiple Airlines Logo
3:46 pm - 6:58 pmRUT  Rutland-ORD Chicago O'Hare Intl
28h 12m1 stop Boston Logan Intl
$521Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
Multiple Airlines Logo
9:38 am - 7:00 pmORD  Chicago O'Hare Intl-RUT Rutland
8h 22m1 stop Boston Logan Intl
Multiple Airlines Logo
11:37 am - 7:29 pmRUT  Rutland-ORD Chicago O'Hare Intl
8h 52m1 stop Boston Logan Intl
$532Multiple Airlines
Wed, Oct 21 - Mon, Oct 26
Multiple Airlines Logo
9:49 pm - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
16h 02m1 stop Boston Logan Intl
Multiple Airlines Logo
3:46 pm - 11:39 pmRUT  Rutland-ORD Chicago O'Hare Intl
8h 53m2 stops Boston Logan Intl Newark
$572Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
Multiple Airlines Logo
6:00 am - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
7h 51m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
7:15 am - 11:39 pmRUT  Rutland-ORD Chicago O'Hare Intl
17h 24m2 stops Boston Logan Intl Newark
$582Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
Multiple Airlines Logo
5:30 pm - 10:29 amORD  Chicago O'Hare Intl-RUT Rutland
15h 59m1 stop Boston Logan Intl
Multiple Airlines Logo
11:37 am - 4:40 pmRUT  Rutland-ORD Chicago O'Hare Intl
6h 03m1 stop Boston Logan Intl
$658Multiple Airlines
Sun, Nov 22 - Sat, Nov 28

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Use the filters below to find and compare flights from Chicago to Rutland that are best for you.

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Price

Cheapest round-trip

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 10/14

9:38 am-10:29 am

1 stop23h 51m

Rutland

Wed 10/21

11:37 am-7:14 pm

1 stop8h 37m

$456
Quickest round-trip

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 10/14

7:30 am-2:51 pm

1 stop6h 21m

Rutland

Wed 10/21

7:15 am-2:26 pm

2 stops8h 11m

$476

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 10/14

6:00 am-2:51 pm

2 stops7h 51m

Rutland

Wed 10/21

7:15 am-2:26 pm

2 stops8h 11m

$486

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 11/18

6:59 am-7:00 pm

1 stop11h 01m

Rutland

Wed 11/25

11:37 am-8:00 am

1 stop21h 23m

$499

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 11/18

5:00 am-7:00 pm

2 stops13h 00m

Rutland

Wed 11/25

11:37 am-9:34 am

1 stop22h 57m

$509

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 12/23

7:55 pm-2:51 pm

1 stop17h 56m

Rutland

Sun 12/27

3:46 pm-6:58 pm

1 stop28h 12m

$521

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 10/21

9:38 am-7:00 pm

1 stop8h 22m

Rutland

Mon 10/26

11:37 am-7:29 pm

1 stop8h 52m

$532

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 12/23

9:49 pm-2:51 pm

1 stop16h 02m

Rutland

Sun 12/27

3:46 pm-11:39 pm

2 stops8h 53m

$572

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Wed 12/23

6:00 am-2:51 pm

2 stops7h 51m

Rutland

Sun 12/27

7:15 am-11:39 pm

2 stops17h 24m

$582

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Sun 11/22

5:30 pm-10:29 am

1 stop15h 59m

Rutland

Sat 11/28

11:37 am-4:40 pm

1 stop6h 03m

$658

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Rutland from

How to get the cheapest flight ticket from Chicago 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 airlines fly to Rutland?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Rutland from Chicago according to our data. United Airlines is the first choice among our users, with 65% 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.

When to book flights from Chicago to Rutland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Rutland according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Rutland (CHI to RUT) flight deals and tips

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

Best Price Found

$228

Fastest flight time

11h 01m

Direct flights

None
The best one-way flight to Rutland from Chicago in the past 72 hours is $228. The best round-trip flight deal from Chicago to Rutland found on momondo in the last 72 hours is $456.
The fastest flight from Chicago to Rutland takes 11h 01m
There are no direct flights from Chicago to Rutland. There are no popular flight routes from Chicago to Rutland.
Search flight deals

Frequently asked questions about flying from Chicago to Rutland

  • How far is Chicago to Rutland by plane?

    Rutland is 751.7 mi away from Chicago. By plane, this route typically takes 11h 01m.

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

    Prices for flights from Chicago to Rutland Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago 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 Chicago to Rutland Airport.

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

    The required travel and health documents for your Rutland Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Rutland Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Rutland?

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

Why use momondo?

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

Finding the right flight to Rutland from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Rutland quick and easy, saving you time and money.

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

All flight searches from Chicago to Rutland on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Chicago to Rutland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Rutland from Chicago. 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.

An easier way to manage your Rutland trip

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