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Cheap flights from Rutland to Chicago from $264

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Rutland to Chicago departing on 6/8. 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
2:13 pm - 7:15 pm
RUT
-
ORD
6h 02m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$490JetBlue
Tue, Jul 14 - Wed, Jul 15
JetBlue Logo
7:00 am - 12:16 pm
RUT
-
ORD
6h 16m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$520JetBlue
Sat, Aug 1 - Wed, Aug 12
JetBlue Logo
2:13 pm - 7:15 pm
RUT
-
ORD
6h 02m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$531JetBlue
Tue, Jul 14 - Wed, Jul 15
JetBlue Logo
7:00 am - 12:59 pm
RUT
-
ORD
6h 59m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$590JetBlue
Sat, Aug 15 - Sun, Aug 16
Multiple Airlines Logo
2:13 pm - 7:34 pm
RUT
-
ORD
6h 21m
1 stop
Multiple Airlines Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$614Multiple Airlines
Mon, Jun 8 - Fri, Jun 12
JetBlue Logo
2:13 pm - 7:25 pm
RUT
-
ORD
6h 12m
1 stop
JetBlue Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$631JetBlue
Fri, Jun 12 - Mon, Jun 15
JetBlue Logo
2:13 pm - 7:25 pm
RUT
-
ORD
6h 12m
1 stop
JetBlue Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$642JetBlue
Fri, Jun 19 - Mon, Jun 22
JetBlue Logo
2:13 pm - 7:25 pm
RUT
-
ORD
6h 12m
1 stop
JetBlue Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$647JetBlue
Fri, Jun 12 - Mon, Jun 15
Multiple Airlines Logo
2:13 pm - 7:34 pm
RUT
-
ORD
6h 21m
1 stop
Multiple Airlines Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$658Multiple Airlines
Sun, Jun 7 - Thu, Jun 11
JetBlue Logo
2:13 pm - 7:25 pm
RUT
-
ORD
6h 12m
1 stop
JetBlue Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$672JetBlue
Thu, Jun 11 - Mon, Jun 15

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
Jul 14
RUT2:13 pmRutland
6h 02m
1 stop
ORD7:15 pmChicago O'Hare Intl
Jul 15
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
$490
JetBlue
Jul 14
RUT2:13 pmRutland
6h 02m
1 stop
ORD7:15 pmChicago O'Hare Intl
Jul 15
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
$531
JetBlue
Aug 15
RUT7:00 amRutland
6h 59m
1 stop
ORD12:59 pmChicago O'Hare Intl
Aug 16
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
$590

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 May 28, 2026.
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

Cheapest round-trip

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 7/14

2:13 pm-7:15 pm

1 stop6h 02m

Chicago O'Hare Intl

Wed 7/15

10:56 am-8:40 pm

1 stop8h 44m

$490

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 8/1

7:00 am-12:16 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 8/12

10:56 am-8:40 pm

1 stop8h 44m

$520

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 7/14

2:13 pm-7:15 pm

1 stop6h 02m

Chicago O'Hare Intl

Wed 7/15

10:56 am-8:40 pm

1 stop8h 44m

$531

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 8/15

7:00 am-12:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 8/16

10:56 am-8:40 pm

1 stop8h 44m

$590

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 6/8

2:13 pm-7:34 pm

1 stop6h 21m

Chicago O'Hare Intl

Fri 6/12

10:56 am-6:45 pm

1 stop6h 49m

$614
Quickest round-trip

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 6/12

2:13 pm-7:25 pm

1 stop6h 12m

Chicago O'Hare Intl

Mon 6/15

10:56 am-6:45 pm

1 stop6h 49m

$631

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 6/19

2:13 pm-7:25 pm

1 stop6h 12m

Chicago O'Hare Intl

Mon 6/22

10:56 am-6:45 pm

1 stop6h 49m

$642

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 6/12

2:13 pm-7:25 pm

1 stop6h 12m

Chicago O'Hare Intl

Mon 6/15

10:56 am-6:45 pm

1 stop6h 49m

$647

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 6/7

2:13 pm-7:34 pm

1 stop6h 21m

Chicago O'Hare Intl

Thu 6/11

10:56 am-8:40 pm

1 stop8h 44m

$658

RutlandChicago

RUT - ORD

RUTORD

Rutland

Thu 6/11

2:13 pm-7:25 pm

1 stop6h 12m

Chicago O'Hare Intl

Mon 6/15

10:56 am-6:45 pm

1 stop6h 49m

$672

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Rutland to Chicago O'Hare Intl Airport

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 Rutland to Chicago O'Hare Intl?

JetBlue is the most popular carrier operating from Rutland to Chicago O'Hare Intl

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

6h 02m

Direct flights

None
The fastest flight from Rutland to Chicago O'Hare Intl Airport takes 6h 02m
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.
Search flight deals

Frequently asked questions about flying from Rutland to Chicago O'Hare Intl Airport

  • 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 6h 02m.

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Tinley Park
South Holland

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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