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Cheap flights from Rutland to Chicago from $359

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 1/31. 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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Find the cheapest flights from Rutland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
11:19 am - 5:43 pm
RUT
-
ORD
7h 24m1 stop
JetBlue Logo
7:45 am - 3:07 pm
ORD
-
RUT
6h 22m1 stop
$359JetBlue
Sat, Jan 31 - Tue, Feb 3
JetBlue Logo
11:19 am - 5:43 pm
RUT
-
ORD
7h 24m1 stop
JetBlue Logo
7:45 am - 3:07 pm
ORD
-
RUT
6h 22m1 stop
$369JetBlue
Mon, Jan 12 - Thu, Jan 15
Multiple Airlines Logo
11:19 am - 6:46 pm
RUT
-
ORD
8h 27m1 stop
Multiple Airlines Logo
7:45 am - 3:07 pm
ORD
-
RUT
6h 22m1 stop
$409Multiple Airlines
Sun, Jan 4 - Thu, Jan 8
Multiple Airlines Logo
11:19 am - 6:46 pm
RUT
-
ORD
8h 27m1 stop
Multiple Airlines Logo
9:40 am - 6:31 pm
ORD
-
RUT
7h 51m2 stops
$463Multiple Airlines
Sun, Jan 4 - Thu, Jan 8

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
Jan 31
RUT11:19 amRutland
7h 24m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 3
ORD7:45 amChicago O'Hare Intl
6h 22m
1 stop
RUT3:07 pmRutland
$359
Find similar
JetBlue
Jan 12
RUT11:19 amRutland
7h 24m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 15
ORD7:45 amChicago O'Hare Intl
6h 22m
1 stop
RUT3:07 pmRutland
$369
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 December 21, 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

Sat 1/31

11:19 am-5:43 pm

1 stop7h 24m

Chicago O'Hare Intl

Tue 2/3

7:45 am-3:07 pm

1 stop6h 22m

$359

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 1/12

11:19 am-5:43 pm

1 stop7h 24m

Chicago O'Hare Intl

Thu 1/15

7:45 am-3:07 pm

1 stop6h 22m

$369

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 1/4

11:19 am-6:46 pm

1 stop8h 27m

Chicago O'Hare Intl

Thu 1/8

7:45 am-3:07 pm

1 stop6h 22m

$409

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 1/4

11:19 am-6:46 pm

1 stop8h 27m

Chicago O'Hare Intl

Thu 1/8

9:40 am-6:31 pm

2 stops7h 51m

$463

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

Fastest flight time

7h 24m

Direct flights

None
The fastest flight from Rutland to Chicago O'Hare Intl Airport takes 7h 24m
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 7h 24m.

  • 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
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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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