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Cheap flights from Rutland to Chicago from $212

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 10/21. 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
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
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
1:09 pm - 8:40 pm
ORD
-
RUT
6h 31m
1 stop
$493JetBlue
Tue, Jul 21 - Sat, Jul 25
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$593JetBlue
Tue, Jul 28 - Fri, Jul 31
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$603JetBlue
Mon, Jul 27 - Fri, Jul 31
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
10:56 am - 6:45 pm
ORD
-
RUT
6h 49m
1 stop
$636JetBlue
Wed, Jul 22 - Sun, Jul 26
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$657JetBlue
Sun, Jul 26 - Fri, Jul 31
JetBlue Logo
2:18 pm - 7:15 pm
RUT
-
ORD
5h 57m
1 stop
JetBlue Logo
10:56 am - 8:40 pm
ORD
-
RUT
8h 44m
1 stop
$693JetBlue
Wed, Jul 29 - Fri, Jul 31

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JetBlue flights from Rutland to Chicago

Our best JetBlue deals on Rutland to Chicago flight tickets
JetBlue
Jul 21
RUT2:18 pmRutland
5h 57m
1 stop
ORD7:15 pmChicago O'Hare Intl
Jul 25
ORD1:09 pmChicago O'Hare Intl
6h 31m
1 stop
RUT8:40 pmRutland
$493
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
JetBlue
Jul 27
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
$603

momondo Fare Finder

 
Customize your flight search to find flights from Rutland to Chicago 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 9, 2026.
Use the filters below to find and compare flights from Rutland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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
Quickest round-trip

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 7/21

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 7/25

1:09 pm-8:40 pm

1 stop6h 31m

$493

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 7/28

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Fri 7/31

10:56 am-8:40 pm

1 stop8h 44m

$593

RutlandChicago

RUT - ORD

RUTORD

Rutland

Mon 7/27

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Fri 7/31

10:56 am-8:40 pm

1 stop8h 44m

$603

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 7/22

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sun 7/26

10:56 am-6:45 pm

1 stop6h 49m

$636

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 7/26

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Fri 7/31

10:56 am-8:40 pm

1 stop8h 44m

$657

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 7/29

2:18 pm-7:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Fri 7/31

10:56 am-8:40 pm

1 stop8h 44m

$693
Cheapest one-way
Quickest one-way

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 10/21

3:35 pm-10:29 pm

1 stop7h 54m

$212

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 10/21

7:15 am-4:34 pm

2 stops10h 19m

$222

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 10/21

11:33 am-1:10 pm

3 stops26h 37m

$263

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Rutland to Chicago

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 airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Rutland according to our data. United Airlines is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Rutland to Chicago

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

Cheap Rutland to Chicago (RUT to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Rutland to Chicago

Fastest flight time

5h 57m

Direct flights

None
The fastest flight from Rutland to Chicago takes 5h 57m
There are no direct flights from Rutland to Chicago. There are no popular flight routes from Rutland to Chicago.
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Frequently asked questions about flying from Rutland to Chicago

  • How far is Rutland to Chicago by plane?

    Chicago is 751.7 mi away from Rutland. In terms of flight time, this usually takes a little over 5h 57m.

  • When did momondo last update prices for flights from Rutland Airport to Chicago?

    Prices for flights from Rutland Airport to Chicago were last updated today.

  • How old do you have to be to fly from Rutland Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Rutland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Chicago from Rutland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Rutland.

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

Price alerts on flights to Chicago from Rutland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport