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Cheap flights from Chicago to Rutland from $309

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Rutland departing on 7/23. 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
6:00 am - 8:40 pm
ORD
-
RUT
13h 40m
2 stops
Multiple Airlines Logo
2:13 pm - 9:55 pm
RUT
-
ORD
8h 42m
2 stops
$382Multiple Airlines
mié., ago. 26 - sáb., ago. 29
Multiple Airlines Logo
6:00 am - 8:40 pm
ORD
-
RUT
13h 40m
2 stops
Multiple Airlines Logo
7:00 am - 9:55 pm
RUT
-
ORD
15h 55m
2 stops
$400Multiple Airlines
vie., ago. 7 - mar., ago. 11
Multiple Airlines Logo
11:01 am - 8:40 pm
ORD
-
RUT
8h 39m
1 stop
Multiple Airlines Logo
2:13 pm - 9:58 pm
RUT
-
ORD
8h 45m
2 stops
$410Multiple Airlines
mié., ago. 26 - sáb., ago. 29
Multiple Airlines Logo
6:05 am - 12:02 pm
ORD
-
RUT
4h 57m
1 stop
Multiple Airlines Logo
7:00 am - 10:30 pm
RUT
-
ORD
16h 30m
1 stop
$412Multiple Airlines
vie., ago. 7 - mar., ago. 11
Multiple Airlines Logo
9:40 pm - 6:45 pm
ORD
-
RUT
20h 05m
1 stop
Multiple Airlines Logo
7:00 am - 10:29 pm
RUT
-
ORD
16h 29m
1 stop
$422Multiple Airlines
lun., ago. 24 - sáb., ago. 29
Multiple Airlines Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
Multiple Airlines Logo
7:00 am - 9:55 pm
RUT
-
ORD
15h 55m
2 stops
$429Multiple Airlines
vie., ago. 7 - mar., ago. 11
Multiple Airlines Logo
1:55 pm - 8:40 pm
ORD
-
RUT
5h 45m
1 stop
Multiple Airlines Logo
9:00 am - 5:34 pm
RUT
-
ORD
9h 34m
2 stops
$434Multiple Airlines
sáb., jul. 4 - mié., jul. 8
Multiple Airlines Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
Multiple Airlines Logo
7:00 am - 12:59 pm
RUT
-
ORD
6h 59m
1 stop
$438Multiple Airlines
mié., ago. 26 - sáb., ago. 29
Multiple Airlines Logo
3:53 pm - 12:02 pm
ORD
-
RUT
19h 09m
2 stops
Multiple Airlines Logo
7:00 am - 8:29 pm
RUT
-
ORD
14h 29m
3 stops
$447Multiple Airlines
vie., ago. 7 - mar., ago. 11
Multiple Airlines Logo
1:55 pm - 8:40 pm
ORD
-
RUT
5h 45m
1 stop
Multiple Airlines Logo
2:13 pm - 7:31 pm
RUT
-
ORD
6h 18m
1 stop
$456Multiple Airlines
sáb., jul. 4 - mié., jul. 8

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JetBlue flights from Chicago to Rutland

Our best JetBlue deals on Chicago to Rutland flight tickets
JetBlue
Jul 16
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
Jul 20
RUT2:13 pmRutland
6h 02m
1 stop
ORD7:15 pmChicago O'Hare Intl
$500
JetBlue
Jul 26
ORD10:56 amChicago O'Hare Intl
6h 49m
1 stop
RUT6:45 pmRutland
Jul 29
RUT2:13 pmRutland
6h 02m
1 stop
ORD7:15 pmChicago O'Hare Intl
$673

momondo Fare Finder

 
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 junio 23, 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 - RUT

ORDRUT

Chicago O'Hare Intl

mié. 8/26

6:00 am-8:40 pm

2 stops13h 40m

Rutland

sáb. 8/29

2:13 pm-9:55 pm

2 stops8h 42m

$382

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

vie. 8/7

6:00 am-8:40 pm

2 stops13h 40m

Rutland

mar. 8/11

7:00 am-9:55 pm

2 stops15h 55m

$400

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

mié. 8/26

11:01 am-8:40 pm

1 stop8h 39m

Rutland

sáb. 8/29

2:13 pm-9:58 pm

2 stops8h 45m

$410

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

vie. 8/7

6:05 am-12:02 pm

1 stop4h 57m

Rutland

mar. 8/11

7:00 am-10:30 pm

1 stop16h 30m

$412

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

lun. 8/24

9:40 pm-6:45 pm

1 stop20h 05m

Rutland

sáb. 8/29

7:00 am-10:29 pm

1 stop16h 29m

$422

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

vie. 8/7

10:56 am-6:45 pm

1 stop6h 49m

Rutland

mar. 8/11

7:00 am-9:55 pm

2 stops15h 55m

$429

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

sáb. 7/4

1:55 pm-8:40 pm

1 stop5h 45m

Rutland

mié. 7/8

9:00 am-5:34 pm

2 stops9h 34m

$434

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

mié. 8/26

10:56 am-8:40 pm

1 stop8h 44m

Rutland

sáb. 8/29

7:00 am-12:59 pm

1 stop6h 59m

$438

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

vie. 8/7

3:53 pm-12:02 pm

2 stops19h 09m

Rutland

mar. 8/11

7:00 am-8:29 pm

3 stops14h 29m

$447
Quickest round-trip

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

sáb. 7/4

1:55 pm-8:40 pm

1 stop5h 45m

Rutland

mié. 7/8

2:13 pm-7:31 pm

1 stop6h 18m

$456

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 63% 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

8h 44m

Direct flights

None
The fastest flight from Chicago to Rutland takes 8h 44m
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 8h 44m.

  • 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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