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Cheap flights from Rutland to Chicago from $364

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Rutland to Chicago departing on 12/5. 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

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Cheap round-trip flights

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JetBlue Logo
11:22 am - 7:43 pmRUT-ORD
9h 21m1 stop
JetBlue Logo
11:25 am - 6:53 pmORD-RUT
6h 28m1 stop
$364JetBlue
Find Deal
Fri, Dec 5 - Tue, Dec 16
JetBlue Logo
11:22 am - 5:31 pmRUT-ORD
7h 09m1 stop
JetBlue Logo
11:30 am - 6:53 pmORD-RUT
6h 23m1 stop
$374JetBlue
Find Deal
Wed, Apr 1 - Sun, Apr 5
JetBlue Logo
11:22 am - 5:31 pmRUT-ORD
7h 09m1 stop
JetBlue Logo
11:30 am - 6:53 pmORD-RUT
6h 23m1 stop
$379JetBlue
Find Deal
Wed, Apr 1 - Sun, Apr 5
JetBlue Logo
7:20 am - 11:43 amRUT-ORD
5h 23m1 stop
JetBlue Logo
12:50 pm - 6:53 pmORD-RUT
5h 03m1 stop
$399JetBlue
Find Deal
Thu, Nov 20 - Wed, Nov 26
JetBlue Logo
7:20 am - 5:55 pmRUT-ORD
11h 35m1 stop
JetBlue Logo
11:20 am - 6:53 pmORD-RUT
6h 33m1 stop
$569JetBlue
Find Deal
Thu, Nov 6 - Mon, Nov 10

JetBlue flights from Rutland to Chicago O'Hare Intl Airport

Our best JetBlue deals on Rutland to Chicago O'Hare Intl Airport flight tickets
JetBlue
Dec 5
RUT11:22 amRutland
9h 21m
1 stop
ORD7:43 pmChicago O'Hare Intl
Dec 16
ORD11:25 amChicago O'Hare Intl
6h 28m
1 stop
RUT6:53 pmRutland
$364
Find similar
JetBlue
Apr 1
RUT11:22 amRutland
7h 09m
1 stop
ORD5:31 pmChicago O'Hare Intl
Apr 5
ORD11:30 amChicago O'Hare Intl
6h 23m
1 stop
RUT6:53 pmRutland
$374
Find similar
JetBlue
Apr 1
RUT11:22 amRutland
7h 09m
1 stop
ORD5:31 pmChicago O'Hare Intl
Apr 5
ORD11:30 amChicago O'Hare Intl
6h 23m
1 stop
RUT6:53 pmRutland
$379
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Rutland to Chicago O'Hare Intl Airport 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 Rutland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 12/5

11:22 am-7:43 pm

1 stop9h 21m

Chicago O'Hare Intl

Tue 12/16

11:25 am-6:53 pm

1 stop6h 28m

$364

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 4/1

11:22 am-5:31 pm

1 stop7h 09m

Chicago O'Hare Intl

Sun 4/5

11:30 am-6:53 pm

1 stop6h 23m

$374

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 4/1

11:22 am-5:31 pm

1 stop7h 09m

Chicago O'Hare Intl

Sun 4/5

11:30 am-6:53 pm

1 stop6h 23m

$379

RutlandChicago

RUT - ORD

RUTORD

Rutland

Thu 11/20

7:20 am-11:43 am

1 stop5h 23m

Chicago O'Hare Intl

Wed 11/26

12:50 pm-6:53 pm

1 stop5h 03m

$399

RutlandChicago

RUT - ORD

RUTORD

Rutland

Thu 11/6

7:20 am-5:55 pm

1 stop11h 35m

Chicago O'Hare Intl

Mon 11/10

11:20 am-6:53 pm

1 stop6h 33m

$569

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

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

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

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

Direct flights

None
There are no direct flights from Rutland to Chicago O'Hare Intl Airport. There are no popular flight routes from Rutland to Chicago O'Hare Intl Airport.
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  • How far is Rutland to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 763.8 mi away from Rutland. By plane, this route typically takes 5h 23m.

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

    Prices for flights from Rutland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Rutland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

    Search flight deals from Rutland to Chicago O'Hare Intl Airport. While viewing offers you’ll have the option to create a Price Alert.

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

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
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Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
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Orland Park
Racine
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Rutland to Chicago for you.

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

Yes. momondo allows you to filter the results for Rutland to Chicago flights to just show those with flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Rutland to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Rutland and alert you when they change.

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