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Cheap flights from Chicago to Rutland from $444

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Rutland departing on 9/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
9:24 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
22h 16m1 stop Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 9:56 amRUT  Rutland-ORD Chicago O'Hare Intl
20h 38m1 stop Boston Logan Intl
$444Multiple Airlines
Sat, Sep 26 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
13h 40m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 7:59 amRUT  Rutland-ORD Chicago O'Hare Intl
18h 41m1 stop Boston Logan Intl
$454Multiple Airlines
Sat, Sep 26 - Mon, Sep 28
Multiple Airlines Logo
7:50 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
23h 50m1 stop Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 2:42 pmRUT  Rutland-ORD Chicago O'Hare Intl
25h 24m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$459Multiple Airlines
Sat, Sep 26 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
13h 40m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 2:42 pmRUT  Rutland-ORD Chicago O'Hare Intl
25h 24m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$469Multiple Airlines
Sat, Sep 26 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 10:38 amORD  Chicago O'Hare Intl-RUT Rutland
27h 38m1 stop Boston Logan Intl
Multiple Airlines Logo
7:15 am - 9:08 amRUT  Rutland-ORD Chicago O'Hare Intl
26h 53m1 stop Boston Logan Intl
$482Multiple Airlines
Mon, Jan 18 - Thu, Jan 21
Multiple Airlines Logo
6:10 am - 6:31 pmORD  Chicago O'Hare Intl-RUT Rutland
11h 21m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 8:00 amRUT  Rutland-ORD Chicago O'Hare Intl
21h 27m1 stop Boston Logan Intl
$488Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
6:00 am - 3:11 pmORD  Chicago O'Hare Intl-RUT Rutland
8h 11m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 11:15 pmRUT  Rutland-ORD Chicago O'Hare Intl
12h 42m2 stops Boston Logan Intl Washington, D.C. Dulles Intl
$492Multiple Airlines
Mon, Jan 18 - Thu, Jan 21
Multiple Airlines Logo
6:10 am - 3:11 pmORD  Chicago O'Hare Intl-RUT Rutland
8h 01m1 stop Boston Logan Intl
Multiple Airlines Logo
3:35 pm - 10:18 pmRUT  Rutland-ORD Chicago O'Hare Intl
31h 43m2 stops Boston Logan Intl Newark
$493Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
6:00 am - 10:38 amORD  Chicago O'Hare Intl-RUT Rutland
27h 38m1 stop Boston Logan Intl
Multiple Airlines Logo
3:35 pm - 2:42 pmRUT  Rutland-ORD Chicago O'Hare Intl
24h 07m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$497Multiple Airlines
Mon, Jan 18 - Thu, Jan 21
Multiple Airlines Logo
6:10 am - 3:11 pmORD  Chicago O'Hare Intl-RUT Rutland
8h 01m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 2:54 pmRUT  Rutland-ORD Chicago O'Hare Intl
28h 21m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$503Multiple Airlines
Thu, Oct 22 - Mon, Oct 26

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Customize your flight search to find flights from Chicago 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 August 10, 2026.
Use the filters below to find and compare flights from Chicago to Rutland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Sat 9/26

9:24 pm-8:40 pm

1 stop22h 16m

Rutland

Mon 9/28

2:18 pm-9:56 am

1 stop20h 38m

$444

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Sat 9/26

6:00 am-8:40 pm

2 stops13h 40m

Rutland

Mon 9/28

2:18 pm-7:59 am

1 stop18h 41m

$454

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Sat 9/26

7:50 pm-8:40 pm

1 stop23h 50m

Rutland

Mon 9/28

2:18 pm-2:42 pm

3 stops25h 24m

$459

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Sat 9/26

6:00 am-8:40 pm

2 stops13h 40m

Rutland

Mon 9/28

2:18 pm-2:42 pm

3 stops25h 24m

$469

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Mon 1/18

6:00 am-10:38 am

1 stop27h 38m

Rutland

Thu 1/21

7:15 am-9:08 am

1 stop26h 53m

$482

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Thu 10/22

6:10 am-6:31 pm

1 stop11h 21m

Rutland

Mon 10/26

11:33 am-8:00 am

1 stop21h 27m

$488
Quickest round-trip

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Mon 1/18

6:00 am-3:11 pm

1 stop8h 11m

Rutland

Thu 1/21

11:33 am-11:15 pm

2 stops12h 42m

$492

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Thu 10/22

6:10 am-3:11 pm

1 stop8h 01m

Rutland

Mon 10/26

3:35 pm-10:18 pm

2 stops31h 43m

$493

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Mon 1/18

6:00 am-10:38 am

1 stop27h 38m

Rutland

Thu 1/21

3:35 pm-2:42 pm

3 stops24h 07m

$497

ChicagoRutland

ORD Chicago O'Hare Intl - RUT Rutland

ORDRUT

Chicago O'Hare Intl

Thu 10/22

6:10 am-3:11 pm

1 stop8h 01m

Rutland

Mon 10/26

11:33 am-2:54 pm

3 stops28h 21m

$503

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 66% 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

Fastest flight time

11h 21m

Direct flights

None
The fastest flight from Chicago to Rutland takes 11h 21m
There are no direct flights from Chicago to Rutland. There are no popular flight routes from Chicago to Rutland.
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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 21m.

  • 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
Chester
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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