ORD - RUT

$251 Find Cheap Flights from Chicago to Rutland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Rutland departing on 12/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

Search hundreds of travel sites at once for deals on flights to Rutland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Rutland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Rutland, as well as popular online travel agencies
In the last 7 days travelers have searched 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago to Rutland (ORD-RUT)

 
These are the cheapest deals for flights from Chicago to Rutland currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Rutland

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Rutland.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:05 am - 2:52 pmORD-RUT
4h 47m1 stop
12:00 pm - 5:59 pmRUT-ORD
6h 59m1 stop
$368JetBlue
Find Deal
Thu, Jan 30 - Sun, Feb 2
7:30 am - 2:52 pmORD-RUT
6h 22m1 stop
12:00 pm - 11:15 pmRUT-ORD
12h 15m2 stops
Thu, Jan 30 - Sun, Feb 2
8:42 am - 2:52 pmORD-RUT
5h 10m1 stop
12:00 pm - 5:59 pmRUT-ORD
6h 59m1 stop
$393JetBlue
Find Deal
Sat, Jan 4 - Sat, Jan 11
8:42 am - 2:52 pmORD-RUT
5h 10m1 stop
12:00 pm - 5:59 pmRUT-ORD
6h 59m1 stop
$403JetBlue
Find Deal
Sun, Jan 5 - Sun, Jan 12
8:20 am - 9:56 amORD-RUT
24h 36m2 stops
4:10 pm - 4:06 pmRUT-ORD
24h 56m2 stops
Thu, Dec 5 - Mon, Dec 9
8:20 am - 9:56 amORD-RUT
24h 36m2 stops
4:10 pm - 4:06 pmRUT-ORD
24h 56m3 stops
Thu, Dec 5 - Mon, Dec 9
6:33 pm - 6:59 pmORD-RUT
23h 26m3 stops
4:10 pm - 4:06 pmRUT-ORD
24h 56m3 stops
Thu, Dec 5 - Mon, Dec 9
7:49 am - 9:56 amORD-RUT
25h 07m2 stops
12:00 pm - 10:32 amRUT-ORD
23h 32m3 stops
Mon, Dec 2 - Tue, Dec 3
8:14 pm - 6:59 pmORD-RUT
21h 45m2 stops
4:10 pm - 4:06 pmRUT-ORD
24h 56m2 stops
Mon, Dec 23 - Mon, Dec 30
7:49 am - 9:56 amORD-RUT
25h 07m2 stops
4:10 pm - 9:07 pmRUT-ORD
29h 57m2 stops
Mon, Dec 2 - Tue, Dec 3

Good to know

Cheapest flight

$251
Flight from Chicago to Rutland

When to book flights from Chicago to Rutland

Are your dates flexible? Find out the best times to travel from Chicago to Rutland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Rutland flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Rutland?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Rutland was $251 for a one-way ticket and $368 for a round-trip.

  • Do I need a passport to fly between Chicago and Rutland?

    A passport is not required to fly from Chicago to Rutland.

  • Which aircraft models fly most regularly from Chicago to Rutland?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago to Rutland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Rutland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Rutland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Rutland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Rutland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Rutland with an airline and back to Chicago with another airline. Booking your flights between Chicago and RUT can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Rutland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Rutland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Rutland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Rutland found on KAYAK in the last 72 hours.
12/24Tue
1 stopJetBlue
5h 10mORD-RUT
$251
12/23Mon
1 stopJetBlue
5h 10mORD-RUT
$326
12/22Sun
1 stopJetBlue
5h 07mORD-RUT
$361

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Last minute flights from Chicago to Rutland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Rutland that are departing in the next 10 days.
11/23Sat
multi-stop
10h 37mORD-RUT
11/26Tue
multi-stop
6h 21mRUT-ORD
$649
11/23Sat
multi-stop
14h 42mORD-RUT
11/26Tue
multi-stop
6h 21mRUT-ORD
$659
11/22Fri
multi-stop
20h 24mORD-RUT
11/27Wed
multi-stop
7h 30mRUT-ORD
$664
11/22Fri
multi-stop
20h 24mORD-RUT
11/26Tue
multi-stop
8h 01mRUT-ORD
$674
11/23Sat
multi-stop
14h 42mORD-RUT
11/26Tue
multi-stop
7h 59mRUT-ORD
$693
11/23Sat
multi-stop
18h 13mORD-RUT
11/27Wed
multi-stop
22h 06mRUT-ORD
$752
11/22Fri
multi-stop
20h 24mORD-RUT
11/26Tue
multi-stop
7h 59mRUT-ORD
$769
11/22Fri
multi-stop
20h 24mORD-RUT
11/27Wed
multi-stop
24h 53mRUT-ORD
$803
11/23Sat
multi-stop
18h 13mORD-RUT
11/27Wed
multi-stop
18h 55mRUT-ORD
$819
11/22Fri
multi-stop
22h 20mORD-RUT
11/27Wed
multi-stop
17h 56mRUT-ORD
$885

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Everything you need to know for your flight from Chicago to Rutland

Information on your arrival and departure airports

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