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Cheap flights from Rutland to Chicago from $388

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 8/24. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Rutland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:05 am - 7:27 pm
RUT
-
ORD
11h 22m
1 stop
Multiple Airlines Logo
11:01 am - 8:40 pm
ORD
-
RUT
8h 39m
1 stop
$388Multiple Airlines
Mon, Aug 24 - Wed, Aug 26
Multiple Airlines Logo
2:18 pm - 7:27 pm
RUT
-
ORD
6h 09m
1 stop
Multiple Airlines Logo
9:40 am - 8:40 pm
ORD
-
RUT
10h 00m
2 stops
$425Multiple Airlines
Mon, Aug 24 - Wed, Aug 26
Multiple Airlines Logo
2:18 pm - 9:58 pm
RUT
-
ORD
8h 40m
2 stops
Multiple Airlines Logo
9:40 am - 8:40 pm
ORD
-
RUT
10h 00m
2 stops
$442Multiple Airlines
Mon, Aug 24 - Wed, Aug 26
Multiple Airlines Logo
9:05 am - 7:58 am
RUT
-
ORD
23h 53m
1 stop
Multiple Airlines Logo
7:45 pm - 6:45 pm
ORD
-
RUT
22h 00m
1 stop
$457Multiple Airlines
Fri, Jul 24 - Mon, Jul 27
Multiple Airlines Logo
7:05 am - 12:16 pm
RUT
-
ORD
6h 11m
1 stop
Multiple Airlines Logo
11:01 am - 8:40 pm
ORD
-
RUT
8h 39m
1 stop
$458Multiple Airlines
Sat, Aug 1 - Fri, Aug 7
Multiple Airlines Logo
7:05 am - 9:58 pm
RUT
-
ORD
15h 53m
2 stops
Multiple Airlines Logo
11:01 am - 8:40 pm
ORD
-
RUT
8h 39m
1 stop
$463Multiple Airlines
Tue, Aug 11 - Mon, Aug 17
JetBlue Logo
7:05 am - 10:06 am
RUT
-
ORD
28h 01m
1 stop
JetBlue Logo
8:10 pm - 12:02 pm
ORD
-
RUT
14h 52m
1 stop
$480JetBlue
Mon, Jul 27 - Wed, Jul 29
Multiple Airlines Logo
2:18 pm - 7:27 pm
RUT
-
ORD
6h 09m
1 stop
Multiple Airlines Logo
11:01 am - 8:40 pm
ORD
-
RUT
8h 39m
1 stop
$494Multiple Airlines
Tue, Aug 11 - Mon, Aug 17
JetBlue Logo
7:05 am - 12:16 pm
RUT
-
ORD
6h 11m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$519JetBlue
Sat, Jul 25 - Wed, Jul 29
Multiple Airlines Logo
9:05 am - 9:17 am
RUT
-
ORD
25h 12m
1 stop
Multiple Airlines Logo
6:12 pm - 12:02 pm
ORD
-
RUT
16h 50m
2 stops
$579Multiple Airlines
Fri, Jul 24 - Mon, Jul 27

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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 27
RUT7:05 amRutland
28h 01m
1 stop
ORD10:06 amChicago O'Hare Intl
Jul 29
ORD8:10 pmChicago O'Hare Intl
14h 52m
1 stop
RUT12:02 pmRutland
$480
JetBlue
Jul 15
RUT2:18 pmRutland
5h 57m
1 stop
ORD7:15 pmChicago O'Hare Intl
Jul 17
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
$519
JetBlue
Jul 28
RUT2:18 pmRutland
5h 57m
1 stop
ORD7:15 pmChicago O'Hare Intl
Jul 31
ORD10:56 amChicago O'Hare Intl
8h 44m
1 stop
RUT8:40 pmRutland
$593

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 July 12, 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

Mon 8/24

9:05 am-7:27 pm

1 stop11h 22m

Chicago O'Hare Intl

Wed 8/26

11:01 am-8:40 pm

1 stop8h 39m

$388

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 8/24

2:18 pm-7:27 pm

1 stop6h 09m

Chicago O'Hare Intl

Wed 8/26

9:40 am-8:40 pm

2 stops10h 00m

$425

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 8/24

2:18 pm-9:58 pm

2 stops8h 40m

Chicago O'Hare Intl

Wed 8/26

9:40 am-8:40 pm

2 stops10h 00m

$442

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 7/24

9:05 am-7:58 am

1 stop23h 53m

Chicago O'Hare Intl

Mon 7/27

7:45 pm-6:45 pm

1 stop22h 00m

$457

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 8/1

7:05 am-12:16 pm

1 stop6h 11m

Chicago O'Hare Intl

Fri 8/7

11:01 am-8:40 pm

1 stop8h 39m

$458

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 8/11

7:05 am-9:58 pm

2 stops15h 53m

Chicago O'Hare Intl

Mon 8/17

11:01 am-8:40 pm

1 stop8h 39m

$463

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 7/27

7:05 am-10:06 am

1 stop28h 01m

Chicago O'Hare Intl

Wed 7/29

8:10 pm-12:02 pm

1 stop14h 52m

$480
Quickest round-trip

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 8/11

2:18 pm-7:27 pm

1 stop6h 09m

Chicago O'Hare Intl

Mon 8/17

11:01 am-8:40 pm

1 stop8h 39m

$494

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 7/25

7:05 am-12:16 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 7/29

10:56 am-8:40 pm

1 stop8h 44m

$519

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 7/24

9:05 am-9:17 am

1 stop25h 12m

Chicago O'Hare Intl

Mon 7/27

6:12 pm-12:02 pm

2 stops16h 50m

$579

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

11h 22m

Direct flights

None
The fastest flight from Rutland to Chicago O'Hare Intl Airport takes 11h 22m
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 11h 22m.

  • 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.

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

  • 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
Schaumburg
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Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
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Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
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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