ORD - RUT

$302 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 3/25. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$457
JetBlue
Fri 5/15Mon 5/18
ORD - RUT • 1 stop
Cheapest one-way
$187
JetBlue
Wed 3/25
ORD - RUT • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Rutland. You'll need at least 1 connection.
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We hope you love your trip to Rutland!
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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

Fri, May 15 - Mon, May 18
JetBlue Logo
6:00 am - 3:07 pm
ORD
-
RUT
8h 07m
1 stop
JetBlue Logo
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
$457JetBlue
Wed, Aug 12 - Mon, Aug 17
JetBlue Logo
10:48 am - 6:31 pm
ORD
-
RUT
6h 43m
1 stop
JetBlue Logo
11:33 am - 7:25 pm
RUT
-
ORD
8h 52m
1 stop
$515JetBlue
Mon, May 18 - Fri, May 22
JetBlue Logo
6:00 am - 3:07 pm
ORD
-
RUT
8h 07m
1 stop
JetBlue Logo
11:19 am - 7:35 pm
RUT
-
ORD
9h 16m
1 stop
$524JetBlue
Fri, Jul 24 - Sun, Jul 26
Multiple Airlines Logo
10:48 am - 6:31 pm
ORD
-
RUT
6h 43m
1 stop
Multiple Airlines Logo
11:33 am - 7:25 pm
RUT
-
ORD
8h 52m
1 stop
$558Multiple Airlines
Fri, May 15 - Mon, May 18
JetBlue Logo
6:00 am - 3:07 pm
ORD
-
RUT
8h 07m
1 stop
JetBlue Logo
3:31 pm - 9:36 pm
RUT
-
ORD
7h 05m
1 stop
$619JetBlue
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
5:05 am - 6:31 pm
ORD
-
RUT
12h 26m
2 stops
Multiple Airlines Logo
7:15 am - 8:03 pm
RUT
-
ORD
13h 48m
2 stops
$772Multiple Airlines
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
5:05 am - 6:31 pm
ORD
-
RUT
12h 26m
2 stops
Multiple Airlines Logo
7:15 am - 4:56 pm
RUT
-
ORD
10h 41m
2 stops
$830Multiple Airlines
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
5:05 am - 6:31 pm
ORD
-
RUT
12h 26m
2 stops
Multiple Airlines Logo
11:19 am - 11:50 am
RUT
-
ORD
25h 31m
3 stops
$831Multiple Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
5:05 am - 6:31 pm
ORD
-
RUT
12h 26m
2 stops
Multiple Airlines Logo
7:15 am - 11:50 am
RUT
-
ORD
29h 35m
3 stops
$841Multiple Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
8:55 am - 3:07 pm
ORD
-
RUT
5h 12m
1 stop
Multiple Airlines Logo
11:19 am - 9:32 pm
RUT
-
ORD
11h 13m
2 stops
$847Multiple Airlines
Booking Insights

Good to know

Cheapest flight$187
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 $187 for a one-way ticket and $457 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)