ORD - RUT

$209 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 10/3. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights from Chicago to Rutland (ORD-RUT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Rutland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Rutland

Sat, Oct 4 - Mon, Oct 6
JetBlue Logo
9:51 am - 7:05 pmORD-RUT
8h 14m1 stop
JetBlue Logo
10:27 am - 6:18 pmRUT-ORD
8h 51m1 stop
$334JetBlue
Find Deal
Sat, Oct 4 - Tue, Oct 7
JetBlue Logo
9:51 am - 7:05 pmORD-RUT
8h 14m1 stop
JetBlue Logo
10:27 am - 6:18 pmRUT-ORD
8h 51m1 stop
$349JetBlue
Find Deal
Thu, Oct 23 - Mon, Oct 27
JetBlue Logo
10:08 am - 6:53 pmORD-RUT
7h 45m1 stop
JetBlue Logo
11:22 am - 5:55 pmRUT-ORD
7h 33m1 stop
$414JetBlue
Find Deal
Wed, Oct 1 - Sat, Oct 4
Logo
9:37 pm - 9:32 amORD-RUT
10h 55m1 stop
Logo
3:58 pm - 8:10 pmRUT-ORD
5h 12m1 stop
$420
Find Deal
Wed, Oct 1 - Sat, Oct 4
Logo
9:37 pm - 9:32 amORD-RUT
10h 55m1 stop
Logo
3:58 pm - 11:15 pmRUT-ORD
8h 17m2 stops
$430
Find Deal
Fri, Oct 24 - Tue, Oct 28
JetBlue Logo
10:08 am - 6:53 pmORD-RUT
7h 45m1 stop
JetBlue Logo
11:22 am - 5:55 pmRUT-ORD
7h 33m1 stop
$439JetBlue
Find Deal
Wed, Oct 1 - Sat, Oct 4
Logo
5:55 pm - 9:32 amORD-RUT
14h 37m2 stops
Logo
3:58 pm - 11:15 pmRUT-ORD
8h 17m2 stops
$440
Find Deal
Fri, Oct 24 - Mon, Oct 27
JetBlue Logo
10:08 am - 6:53 pmORD-RUT
7h 45m1 stop
JetBlue Logo
11:22 am - 5:55 pmRUT-ORD
7h 33m1 stop
$454JetBlue
Find Deal
Fri, Oct 3 - Mon, Oct 6
JetBlue Logo
9:51 am - 7:05 pmORD-RUT
8h 14m1 stop
JetBlue Logo
10:27 am - 6:18 pmRUT-ORD
8h 51m1 stop
$469JetBlue
Find Deal
Fri, Oct 3 - Mon, Oct 6
Logo
2:20 pm - 9:32 amORD-RUT
18h 12m2 stops
Logo
3:58 pm - 10:35 pmRUT-ORD
7h 37m1 stop
$477
Find Deal

Everything you should know

Cheapest round-trip
$334
JetBlue
Sat 10/4Mon 10/6
ORD - RUT • 1 stop
Cheapest one-way
$209
Multiple Airlines
Fri 10/3
ORD - RUT • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Rutland!
Booking Insights

Good to know

Cheapest flight$209
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 $209 for a one-way ticket and $334 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.

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

Information on your arrival and departure airports

Chicago (ORD)
Rutland (RUT)

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