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ORD - RUT

Find cheap flights from Chicago to Rutland from $490

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Rutland departing on 9/24. 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
Mon 6/3
Mon 6/10

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 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
10:42 am - 7:05 pmORD-RUT
7h 23m1 stop
11:45 am - 7:40 pmRUT-ORD
8h 55m1 stop
$490JetBlue
Find Deal
Tue, Sep 24 - Wed, Sep 25
9:45 pm - 7:05 pmORD-RUT
20h 20m1 stop
11:45 am - 7:50 amRUT-ORD
21h 05m1 stop
$589
Find Deal
Sun, Jun 9 - Sat, Jun 15
9:45 pm - 7:05 pmORD-RUT
20h 20m1 stop
4:35 pm - 9:43 amRUT-ORD
18h 08m2 stops
$628
Find Deal
Sun, Jun 9 - Sat, Jun 15

Good to know

Cheapest flight

$490
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 $490 for a round-trip ticket.

  • 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

Chicago - Rutland Flights

Departure:

Chicago (ORD)United States

Destination:

Rutland (RUT)United States

Return flight deals:

Rutland - Chicago

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