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.

$222 Cheap Flights from Chicago to Rutland in 2025

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Find the cheapest flights from Chicago to Rutland

Round-trip

One-way

Cheap round-trip flights

6:30 am - 1:32 pmORD-RUT

6h 02m1 stop

3:58 pm - 7:56 amRUT-ORD

16h 58m1 stop

$467

Find Deal

Thu, Oct 2 - Mon, Oct 6

7:15 am - 7:05 pmORD-RUT

10h 50m2 stops

10:27 am - 8:05 amRUT-ORD

22h 38m1 stop

$477

Find Deal

Wed, Aug 27 - Wed, Sep 3

7:15 am - 7:05 pmORD-RUT

10h 50m2 stops

10:27 am - 7:48 pmRUT-ORD

10h 21m2 stops

$487

Find Deal

Wed, Aug 27 - Wed, Sep 3

6:30 am - 1:32 pmORD-RUT

6h 02m1 stop

10:27 am - 11:30 pmRUT-ORD

14h 03m2 stops

$512

Find Deal

Thu, Oct 2 - Mon, Oct 6

3:48 pm - 1:32 pmORD-RUT

20h 44m1 stop

3:58 pm - 9:41 amRUT-ORD

18h 43m1 stop

$522

Find Deal

Wed, Aug 27 - Wed, Sep 3

9:51 am - 7:05 pmORD-RUT

8h 14m1 stop

7:20 am - 8:50 pmRUT-ORD

14h 30m2 stops

$543JetBlue

Find Deal

Fri, Oct 3 - Sun, Oct 5

5:55 pm - 9:32 amORD-RUT

14h 37m2 stops

3:58 pm - 11:30 pmRUT-ORD

8h 32m2 stops

$557

Find Deal

Fri, Oct 3 - Sun, Oct 5

8:40 am - 7:05 pmORD-RUT

9h 25m1 stop

10:27 am - 3:32 pmRUT-ORD

6h 05m1 stop

$569JetBlue

Find Deal

Thu, Aug 14 - Mon, Aug 18

1:30 pm - 9:32 amORD-RUT

19h 02m1 stop

7:20 am - 2:25 pmRUT-ORD

8h 05m1 stop

$570

Find Deal

Fri, Oct 3 - Sun, Oct 5

7:30 am - 1:32 pmORD-RUT

5h 02m1 stop

3:58 pm - 7:38 amRUT-ORD

16h 40m2 stops

$636

Find Deal

Thu, Oct 2 - Sun, Oct 5

JetBlue flights from Chicago to Rutland

Our best JetBlue deals on Chicago to Rutland flight tickets

JetBlue

Oct 3

ORD9:51 amChicago O'Hare Intl

8h 14m

1 stop

RUT7:05 pmRutland

Oct 5

RUT7:20 amRutland

14h 30m

2 stops

ORD8:50 pmChicago O'Hare Intl

$543

Find similar

JetBlue

Aug 14

ORD8:40 amChicago O'Hare Intl

9h 25m

1 stop

RUT7:05 pmRutland

Aug 18

RUT10:27 amRutland

6h 05m

1 stop

ORD3:32 pmChicago O'Hare Intl

$569

Find similar

JetBlue

Oct 10

ORD9:42 amChicago O'Hare Intl

8h 23m

1 stop

RUT7:05 pmRutland

Oct 12

RUT10:27 amRutland

8h 28m

1 stop

ORD5:55 pmChicago O'Hare Intl

$654

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 10/2

6:30 am-1:32 pm

1 stop6h 02m

Rutland

Mon 10/6

3:58 pm-7:56 am

1 stop16h 58m

$467

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 8/27

7:15 am-7:05 pm

2 stops10h 50m

Rutland

Wed 9/3

10:27 am-8:05 am

1 stop22h 38m

$477

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 8/27

7:15 am-7:05 pm

2 stops10h 50m

Rutland

Wed 9/3

10:27 am-7:48 pm

2 stops10h 21m

$487

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 10/2

6:30 am-1:32 pm

1 stop6h 02m

Rutland

Mon 10/6

10:27 am-11:30 pm

2 stops14h 03m

$512

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 8/27

3:48 pm-1:32 pm

1 stop20h 44m

Rutland

Wed 9/3

3:58 pm-9:41 am

1 stop18h 43m

$522

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 10/3

9:51 am-7:05 pm

1 stop8h 14m

Rutland

Sun 10/5

7:20 am-8:50 pm

2 stops14h 30m

$543

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 10/3

5:55 pm-9:32 am

2 stops14h 37m

Rutland

Sun 10/5

3:58 pm-11:30 pm

2 stops8h 32m

$557

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 8/14

8:40 am-7:05 pm

1 stop9h 25m

Rutland

Mon 8/18

10:27 am-3:32 pm

1 stop6h 05m

$569

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 10/3

1:30 pm-9:32 am

1 stop19h 02m

Rutland

Sun 10/5

7:20 am-2:25 pm

1 stop8h 05m

$570

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 10/2

7:30 am-1:32 pm

1 stop5h 02m

Rutland

Sun 10/5

3:58 pm-7:38 am

2 stops16h 40m

$636

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first

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 is the cheapest airline that flies from Chicago to Rutland?

JetBlue is the most popular carrier operating from Chicago 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 Chicago according to our data. United Airlines is the first choice among our users, with 60% 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	$222
Fastest flight time	5h 02m
Direct flights	None
Airports in Rutland	1 airport

The best one-way flight to Rutland from Chicago in the past 72 hours is $222. The best round-trip flight deal from Chicago to Rutland found on momondo in the last 72 hours is $467.

The fastest flight from Chicago to Rutland takes 5h 02m

There are no direct flights from Chicago to Rutland. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Rutland Airport.

There is 1 airport near Rutland: Rutland (RUT)

Search flight deals

How far is Chicago to Rutland by plane?
Rutland is 751.7 mi away from Chicago. By plane, this route typically takes 5h 02m.
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.

Lake George

Killington

Ludlow

Ticonderoga

Stratton

Dover

Londonderry

Chester

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago to Rutland from $222

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 9/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Rutland

Cheap round-trip flights

Cheap one-way flights

JetBlue flights from Chicago to Rutland

Our best JetBlue deals on Chicago to Rutland flight tickets

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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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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 is the cheapest airline that flies from Chicago to Rutland?

JetBlue is the most popular carrier operating from Chicago to Rutland

What airlines fly to Rutland?

When to book flights from Chicago to Rutland

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

Fastest flight time

Direct flights

Airports in Rutland

How far is Chicago to Rutland by plane?

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

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

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

Traveling to a place near Rutland?

Why use momondo?

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

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

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

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

An easier way to manage your Rutland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Vermont