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Cheap flights from Rutland to Chicago from $224

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 7/28. 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

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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
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
JetBlue Logo
7:21 am - 3:07 pm
ORD
-
RUT
6h 46m
1 stop
$452JetBlue
Sat, May 2 - Tue, May 5
Multiple Airlines Logo
11:19 am - 9:39 pm
RUT
-
ORD
11h 20m
1 stop
Multiple Airlines Logo
9:41 am - 6:31 pm
ORD
-
RUT
7h 50m
1 stop
$513Multiple Airlines
Sat, Apr 18 - Wed, Apr 22
Multiple Airlines Logo
3:31 pm - 9:39 pm
RUT
-
ORD
7h 08m
1 stop
Multiple Airlines Logo
6:00 am - 6:31 pm
ORD
-
RUT
11h 31m
1 stop
$528Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
JetBlue Logo
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
JetBlue Logo
6:00 am - 3:07 pm
ORD
-
RUT
8h 07m
1 stop
$543JetBlue
Fri, May 1 - Mon, May 4
JetBlue Logo
11:19 am - 7:35 pm
RUT
-
ORD
9h 16m
1 stop
JetBlue Logo
10:56 am - 6:31 pm
ORD
-
RUT
6h 35m
1 stop
$545JetBlue
Tue, Jun 2 - Thu, Jun 11
Multiple Airlines Logo
3:31 pm - 9:39 pm
RUT
-
ORD
7h 08m
1 stop
Multiple Airlines Logo
8:31 am - 6:31 pm
ORD
-
RUT
9h 00m
2 stops
$572Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
3:31 pm - 9:39 pm
RUT
-
ORD
7h 08m
1 stop
Multiple Airlines Logo
6:00 am - 3:07 pm
ORD
-
RUT
8h 07m
1 stop
$573Multiple Airlines
Sun, Apr 19 - Thu, Apr 23
JetBlue Logo
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
JetBlue Logo
9:49 am - 6:31 pm
ORD
-
RUT
7h 42m
1 stop
$590JetBlue
Wed, Apr 29 - Sun, May 3
JetBlue Logo
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
JetBlue Logo
9:49 am - 6:31 pm
ORD
-
RUT
7h 42m
1 stop
$595JetBlue
Wed, Apr 29 - Sun, May 3
Multiple Airlines Logo
3:31 pm - 12:24 am
RUT
-
ORD
33h 53m
3 stops
Multiple Airlines Logo
5:05 am - 6:31 pm
ORD
-
RUT
36h 26m
3 stops
$661Multiple Airlines
Sun, Apr 19 - Thu, Apr 23

JetBlue flights from Rutland to Chicago

Our best JetBlue deals on Rutland to Chicago flight tickets
JetBlue
May 2
RUT3:31 pmRutland
7h 05m
1 stop
ORD9:36 pmChicago O'Hare Intl
May 5
ORD7:21 amChicago O'Hare Intl
6h 46m
1 stop
RUT3:07 pmRutland
$452
JetBlue
May 1
RUT3:31 pmRutland
7h 05m
1 stop
ORD9:36 pmChicago O'Hare Intl
May 4
ORD6:00 amChicago O'Hare Intl
8h 07m
1 stop
RUT3:07 pmRutland
$543
JetBlue
Jun 2
RUT11:19 amRutland
9h 16m
1 stop
ORD7:35 pmChicago O'Hare Intl
Jun 11
ORD10:56 amChicago O'Hare Intl
6h 35m
1 stop
RUT6:31 pmRutland
$545

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 April 5, 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
Quickest round-trip

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 5/2

3:31 pm-9:36 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 5/5

7:21 am-3:07 pm

1 stop6h 46m

$452

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sat 4/18

11:19 am-9:39 pm

1 stop11h 20m

Chicago O'Hare Intl

Wed 4/22

9:41 am-6:31 pm

1 stop7h 50m

$513

RutlandChicago

RUT - ORD

RUTORD

Rutland

Thu 4/16

3:31 pm-9:39 pm

1 stop7h 08m

Chicago O'Hare Intl

Mon 4/20

6:00 am-6:31 pm

1 stop11h 31m

$528

RutlandChicago

RUT - ORD

RUTORD

Rutland

Fri 5/1

3:31 pm-9:36 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/4

6:00 am-3:07 pm

1 stop8h 07m

$543

RutlandChicago

RUT - ORD

RUTORD

Rutland

Tue 6/2

11:19 am-7:35 pm

1 stop9h 16m

Chicago O'Hare Intl

Thu 6/11

10:56 am-6:31 pm

1 stop6h 35m

$545

RutlandChicago

RUT - ORD

RUTORD

Rutland

Thu 4/16

3:31 pm-9:39 pm

1 stop7h 08m

Chicago O'Hare Intl

Mon 4/20

8:31 am-6:31 pm

2 stops9h 00m

$572

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 4/19

3:31 pm-9:39 pm

1 stop7h 08m

Chicago O'Hare Intl

Thu 4/23

6:00 am-3:07 pm

1 stop8h 07m

$573

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 4/29

3:31 pm-9:36 pm

1 stop7h 05m

Chicago O'Hare Intl

Sun 5/3

9:49 am-6:31 pm

1 stop7h 42m

$590

RutlandChicago

RUT - ORD

RUTORD

Rutland

Wed 4/29

3:31 pm-9:36 pm

1 stop7h 05m

Chicago O'Hare Intl

Sun 5/3

9:49 am-6:31 pm

1 stop7h 42m

$595

RutlandChicago

RUT - ORD

RUTORD

Rutland

Sun 4/19

3:31 pm-12:24 am

3 stops33h 53m

Chicago O'Hare Intl

Thu 4/23

5:05 am-6:31 pm

3 stops36h 26m

$661

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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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 is the cheapest airline that flies from Rutland to Chicago?

JetBlue is the most popular carrier operating from Rutland to Chicago

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 58% 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

7h 05m

Direct flights

None
The fastest flight from Rutland to Chicago takes 7h 05m
There are no direct flights from Rutland to Chicago. There are no popular flight routes from Rutland to Chicago.
Search flight deals

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 7h 05m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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