Latest deals
When to book
FAQs
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Rutland from $349

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 O'Hare Intl Airport to Rutland departing on 3/25. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago O'Hare Intl Airport to Rutland

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
12:10 pm - 6:53 pmORD-RUT
5h 43m1 stop
JetBlue Logo
11:22 am - 5:31 pmRUT-ORD
7h 09m1 stop
$349JetBlue
Find Deal
Wed, Mar 25 - Thu, Mar 26
JetBlue Logo
12:10 pm - 6:53 pmORD-RUT
5h 43m1 stop
JetBlue Logo
11:22 am - 5:31 pmRUT-ORD
7h 09m1 stop
$359JetBlue
Find Deal
Wed, Mar 25 - Thu, Mar 26
JetBlue Logo
11:20 am - 6:53 pmORD-RUT
6h 33m1 stop
JetBlue Logo
7:20 am - 5:55 pmRUT-ORD
11h 35m1 stop
$389JetBlue
Find Deal
Thu, Nov 6 - Mon, Nov 10
JetBlue Logo
12:10 pm - 6:53 pmORD-RUT
5h 43m1 stop
JetBlue Logo
11:22 am - 5:31 pmRUT-ORD
7h 09m1 stop
$409JetBlue
Find Deal
Wed, Mar 25 - Thu, Mar 26
Multiple Airlines Logo
8:28 am - 10:27 amORD-RUT
24h 59m3 stops
Multiple Airlines Logo
7:20 am - 12:53 pmRUT-ORD
30h 33m3 stops
$503Multiple Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
Multiple Airlines Logo
3:26 pm - 10:27 amORD-RUT
18h 01m2 stops
Multiple Airlines Logo
7:20 am - 12:53 pmRUT-ORD
30h 33m3 stops
$538Multiple Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
Multiple Airlines Logo
3:26 pm - 10:27 amORD-RUT
18h 01m2 stops
Multiple Airlines Logo
7:20 am - 11:06 pmRUT-ORD
16h 46m2 stops
$627Multiple Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10

JetBlue flights from Chicago O'Hare Intl Airport to Rutland

Our best JetBlue deals on Chicago O'Hare Intl Airport to Rutland flight tickets
JetBlue
Mar 25
ORD12:10 pmChicago O'Hare Intl
5h 43m
1 stop
RUT6:53 pmRutland
Mar 26
RUT11:22 amRutland
7h 09m
1 stop
ORD5:31 pmChicago O'Hare Intl
$349
Find similar
JetBlue
Mar 25
ORD12:10 pmChicago O'Hare Intl
5h 43m
1 stop
RUT6:53 pmRutland
Mar 26
RUT11:22 amRutland
7h 09m
1 stop
ORD5:31 pmChicago O'Hare Intl
$359
Find similar
JetBlue
Nov 6
ORD11:20 amChicago O'Hare Intl
6h 33m
1 stop
RUT6:53 pmRutland
Nov 10
RUT7:20 amRutland
11h 35m
1 stop
ORD5:55 pmChicago O'Hare Intl
$389
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 October 23, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Rutland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 3/25

12:10 pm-6:53 pm

1 stop5h 43m

Rutland

Thu 3/26

11:22 am-5:31 pm

1 stop7h 09m

$349

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 3/25

12:10 pm-6:53 pm

1 stop5h 43m

Rutland

Thu 3/26

11:22 am-5:31 pm

1 stop7h 09m

$359

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 11/6

11:20 am-6:53 pm

1 stop6h 33m

Rutland

Mon 11/10

7:20 am-5:55 pm

1 stop11h 35m

$389

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Wed 3/25

12:10 pm-6:53 pm

1 stop5h 43m

Rutland

Thu 3/26

11:22 am-5:31 pm

1 stop7h 09m

$409

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 11/6

8:28 am-10:27 am

3 stops24h 59m

Rutland

Mon 11/10

7:20 am-12:53 pm

3 stops30h 33m

$503

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 11/6

3:26 pm-10:27 am

2 stops18h 01m

Rutland

Mon 11/10

7:20 am-12:53 pm

3 stops30h 33m

$538

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 11/6

3:26 pm-10:27 am

2 stops18h 01m

Rutland

Mon 11/10

7:20 am-11:06 pm

2 stops16h 46m

$627

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Chicago O'Hare Intl Airport to Rutland

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

Cheap Chicago O'Hare Intl Airport to Rutland (ORD to RUT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Rutland

Direct flights

None
There are no direct flights from Chicago O'Hare Intl Airport to Rutland. There are no popular flight routes from Chicago O'Hare Intl Airport to Rutland.
Search flight deals

  • How far is Chicago O'Hare Intl to Rutland by plane?

    Rutland is 763.8 mi away from Chicago O'Hare Intl. A reasonable flight in good conditions will take 5h 43m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Rutland Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Rutland Airport refresh daily.

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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.

  • How do I get Price Alerts for flights from Chicago O'Hare Intl Airport to Rutland?

    Confirm your travel details to search for the latest offers for flights from Chicago O'Hare Intl Airport to Rutland. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Chicago O'Hare Intl Airport to Rutland with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Rutland?

Book flights to Rutland if you plan to visit one of these locations
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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Rutland. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Rutland from Chicago with this policy.

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

Once all potential Chicago to Rutland flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Rutland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/22
Sat 11/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Airports servicing Vermont

Burlington Airport