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Cheap flights from Chicago O'Hare Intl Airport to Rutland from $336

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 11/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Rutland

Cheap round-trip flights

JetBlue Logo
11:30 am - 6:53 pmORD-RUT
6h 23m1 stop
JetBlue Logo
12:00 pm - 7:40 pmRUT-ORD
8h 40m1 stop
$336JetBlue
Find Deal
Wed, Nov 19 - Sat, Nov 22
JetBlue Logo
9:42 am - 7:05 pmORD-RUT
8h 23m1 stop
JetBlue Logo
10:27 am - 5:55 pmRUT-ORD
8h 28m1 stop
$494JetBlue
Find Deal
Thu, Oct 9 - Tue, Oct 14
JetBlue Logo
9:42 am - 6:53 pmORD-RUT
8h 11m1 stop
JetBlue Logo
12:00 pm - 7:05 pmRUT-ORD
8h 05m1 stop
$519JetBlue
Find Deal
Thu, Oct 23 - Sun, Oct 26
Logo
6:30 am - 7:05 pmORD-RUT
11h 35m1 stop
Logo
3:58 pm - 7:56 amRUT-ORD
16h 58m1 stop
$561
Find Deal
Fri, Oct 10 - Mon, Oct 13
Logo
5:16 pm - 1:32 pmORD-RUT
19h 16m2 stops
Logo
7:20 am - 10:22 pmRUT-ORD
16h 02m2 stops
$574
Find Deal
Thu, Aug 21 - Mon, Aug 25
Logo
11:36 am - 7:05 pmORD-RUT
30h 29m3 stops
Logo
7:20 am - 10:22 pmRUT-ORD
16h 02m2 stops
$586
Find Deal
Thu, Aug 21 - Mon, Aug 25
Logo
12:05 pm - 1:32 pmORD-RUT
24h 27m3 stops
Logo
7:20 am - 10:31 amRUT-ORD
28h 11m3 stops
$628
Find Deal
Thu, Aug 21 - Mon, Aug 25
JetBlue Logo
9:42 am - 7:05 pmORD-RUT
8h 23m1 stop
JetBlue Logo
12:00 pm - 5:55 pmRUT-ORD
6h 55m1 stop
$646JetBlue
Find Deal
Tue, Oct 14 - Tue, Oct 21

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
Nov 19
ORD11:30 amChicago O'Hare Intl
6h 23m
1 stop
RUT6:53 pmRutland
Nov 22
RUT12:00 pmRutland
8h 40m
1 stop
ORD7:40 pmChicago O'Hare Intl
$336
Find similar
JetBlue
Oct 9
ORD9:42 amChicago O'Hare Intl
8h 23m
1 stop
RUT7:05 pmRutland
Oct 14
RUT10:27 amRutland
8h 28m
1 stop
ORD5:55 pmChicago O'Hare Intl
$494
Find similar
JetBlue
Oct 23
ORD9:42 amChicago O'Hare Intl
8h 11m
1 stop
RUT6:53 pmRutland
Oct 26
RUT12:00 pmRutland
8h 05m
1 stop
ORD7:05 pmChicago O'Hare Intl
$519
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 August 7, 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 11/19

11:30 am-6:53 pm

1 stop6h 23m

Rutland

Sat 11/22

12:00 pm-7:40 pm

1 stop8h 40m

$336

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 10/9

9:42 am-7:05 pm

1 stop8h 23m

Rutland

Tue 10/14

10:27 am-5:55 pm

1 stop8h 28m

$494

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 10/23

9:42 am-6:53 pm

1 stop8h 11m

Rutland

Sun 10/26

12:00 pm-7:05 pm

1 stop8h 05m

$519

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Fri 10/10

6:30 am-7:05 pm

1 stop11h 35m

Rutland

Mon 10/13

3:58 pm-7:56 am

1 stop16h 58m

$561

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 8/21

5:16 pm-1:32 pm

2 stops19h 16m

Rutland

Mon 8/25

7:20 am-10:22 pm

2 stops16h 02m

$574

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 8/21

11:36 am-7:05 pm

3 stops30h 29m

Rutland

Mon 8/25

7:20 am-10:22 pm

2 stops16h 02m

$586

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Thu 8/21

12:05 pm-1:32 pm

3 stops24h 27m

Rutland

Mon 8/25

7:20 am-10:31 am

3 stops28h 11m

$628

ChicagoRutland

ORD - RUT

ORDRUT

Chicago O'Hare Intl

Tue 10/14

9:42 am-7:05 pm

1 stop8h 23m

Rutland

Tue 10/21

12:00 pm-5:55 pm

1 stop6h 55m

$646

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

Best Price Found

$336

Fastest flight time

6h 23m

Direct flights

None

Airports in Rutland

1 airport
The best flight deal from Chicago O'Hare Intl Airport to Rutland found on momondo in the last 72 hours is $336
The fastest flight from Chicago O'Hare Intl Airport to Rutland takes 6h 23m
There are no direct flights from Chicago O'Hare Intl Airport 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 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 6h 23m.

  • 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.

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