ORD - RUT

$758 Find Cheap Flights from Chicago to Rutland - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$758
Typical prices: $374-$399
Multiple Airlines
Mon 2/12Wed 2/14
ORD - RUT • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago O'Hare Intl Airport and Rutland. You'll need to take a connecting flight to reach the destination.
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Cheap Flights from Chicago to Rutland (ORD-RUT)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Rutland

Fri, Feb 12 - Sun, Feb 14
Multiple Airlines Logo
7:00 am - 7:00 pmORD  Chicago O'Hare Intl-RUT Rutland
11h 00m1 stop Boston Logan Intl
Multiple Airlines Logo
3:46 pm - 11:16 amRUT  Rutland-ORD Chicago O'Hare Intl
20h 30m1 stop Boston Logan Intl
$758Multiple Airlines
Fri, Feb 12 - Sun, Feb 14
Multiple Airlines Logo
1:30 pm - 2:51 pmORD  Chicago O'Hare Intl-RUT Rutland
24h 21m1 stop Boston Logan Intl
Multiple Airlines Logo
7:15 am - 8:22 pmRUT  Rutland-ORD Chicago O'Hare Intl
14h 07m2 stops Boston Logan Intl Newark
$766Multiple Airlines
Fri, Feb 12 - Sun, Feb 14
Multiple Airlines Logo
4:29 pm - 10:29 amORD  Chicago O'Hare Intl-RUT Rutland
17h 00m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
7:15 am - 9:59 pmRUT  Rutland-ORD Chicago O'Hare Intl
15h 44m2 stops Boston Logan Intl Newark
$776Multiple Airlines
Wed, Nov 11 - Sun, Nov 15
Multiple Airlines Logo
3:59 pm - 10:29 amORD  Chicago O'Hare Intl-RUT Rutland
17h 30m2 stops Seattle/Tacoma Intl Boston Logan Intl
Multiple Airlines Logo
7:15 am - 12:00 pmRUT  Rutland-ORD Chicago O'Hare Intl
5h 45m1 stop Boston Logan Intl
$1,031Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Rutland flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What is the cheapest layover airport when flying from Chicago O'Hare Intl Airport to Rutland?

Flights via Boston Logan Intl (BOS) offer the most affordable fares, with an average round-trip price of $445. Based on KAYAK data over the past 3 months.

When flying from Chicago O'Hare Intl Airport to Rutland which airport offers the shortest layover?

Boston Logan Intl (BOS) had the shortest average connection time for Chicago O'Hare Intl Airport to Rutland layovers at 5h 11m over the past 3 months.

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Key details for Chicago O'Hare Intl Airport to Rutland flights

Cheapest flight

$758
Round-trip flight from Chicago O'Hare Intl Airport 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

Your Chicago O'Hare Intl Airport to Rutland flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How long is a flight from Chicago O'Hare Intl Airport to Rutland?

    A nonstop flight from Chicago O'Hare Intl Airport to Rutland takes 00m, covering 765 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Rutland?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • Have flight prices from Chicago O'Hare Intl Airport to Rutland changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route varied from about $758 to $1,031. That means the highest observed fare was about 36% higher than the lowest one.

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Rutland?

    Flights from Chicago O'Hare Intl Airport to Rutland usually depart from Chicago O'Hare Intl (ORD) and arrive at Rutland (RUT).

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Rutland pass through?

    Most connecting flights from Chicago O'Hare Intl Airport to Rutland pass through Boston Logan Intl (BOS), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Rutland?

    Yes. Flexible dates can save you up to 28% on flights from Chicago O'Hare Intl Airport to Rutland. Friday is the cheapest departure day at $374 round-trip on average, while Thursday is the most expensive at $518, a difference of $144.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What is the time difference between Chicago O'Hare Intl Airport and Rutland?

    Rutland is 1 hour ahead of Chicago O'Hare Intl Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Chicago O'Hare Intl Airport to Rutland flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Friday departure and avoid flying on Thursday. On this route, Friday flights average $374, about $144 less than Thursday fares (28% savings) based on the last 12 months.

More options for your flight from Chicago to Rutland

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