ORD - RUT

$265 Find Cheap Flights from Chicago to Rutland - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$520
Typical prices: $374-$399
Multiple Airlines
Thu 11/22Tue 11/27
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

Sun, Nov 22 - Fri, Nov 27
Multiple Airlines Logo
5:30 pm - 10:38 amORD  Chicago O'Hare Intl-RUT Rutland
16h 08m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 4:40 pmRUT  Rutland-ORD Chicago O'Hare Intl
6h 07m1 stop Boston Logan Intl
$520Multiple Airlines
Fri, Oct 9 - Mon, Oct 12
Multiple Airlines Logo
7:50 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
23h 50m1 stop Boston Logan Intl
Multiple Airlines Logo
9:05 am - 7:59 amRUT  Rutland-ORD Chicago O'Hare Intl
23h 54m1 stop Boston Logan Intl
$596Multiple Airlines
Sat, Nov 21 - Fri, Nov 27
Multiple Airlines Logo
11:00 am - 6:31 pmORD  Chicago O'Hare Intl-RUT Rutland
6h 31m1 stop Boston Logan Intl
Multiple Airlines Logo
7:15 am - 4:40 pmRUT  Rutland-ORD Chicago O'Hare Intl
10h 25m1 stop Boston Logan Intl
$608Multiple Airlines
Fri, Nov 20 - Sun, Nov 29
Multiple Airlines Logo
5:30 pm - 3:11 pmORD  Chicago O'Hare Intl-RUT Rutland
20h 41m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 9:59 amRUT  Rutland-ORD Chicago O'Hare Intl
23h 26m1 stop Boston Logan Intl
$608Multiple Airlines
Sat, Nov 21 - Sun, Nov 29
Multiple Airlines Logo
5:30 pm - 3:11 pmORD  Chicago O'Hare Intl-RUT Rutland
20h 41m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 9:59 amRUT  Rutland-ORD Chicago O'Hare Intl
23h 26m1 stop Boston Logan Intl
$609Multiple Airlines
Fri, Oct 9 - Mon, Oct 12
Multiple Airlines Logo
9:24 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
22h 16m1 stop Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 2:42 pmRUT  Rutland-ORD Chicago O'Hare Intl
25h 24m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$631Multiple Airlines
Fri, Oct 9 - Mon, Oct 12
Multiple Airlines Logo
9:35 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
22h 05m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
9:05 am - 7:59 amRUT  Rutland-ORD Chicago O'Hare Intl
23h 54m1 stop Boston Logan Intl
$675Multiple Airlines
Fri, Oct 9 - Mon, Oct 12
Multiple Airlines Logo
9:35 pm - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
22h 05m2 stops Newark Boston Logan Intl
Multiple Airlines Logo
2:18 pm - 2:42 pmRUT  Rutland-ORD Chicago O'Hare Intl
25h 24m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl
$710Multiple Airlines
Fri, Nov 20 - Sat, Nov 28
Multiple Airlines Logo
11:00 am - 10:38 amORD  Chicago O'Hare Intl-RUT Rutland
22h 38m1 stop Boston Logan Intl
Multiple Airlines Logo
11:33 am - 4:40 pmRUT  Rutland-ORD Chicago O'Hare Intl
6h 07m1 stop Boston Logan Intl
$763Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
Multiple Airlines Logo
9:50 am - 8:40 pmORD  Chicago O'Hare Intl-RUT Rutland
9h 50m1 stop Boston Logan Intl
Multiple Airlines Logo
9:05 am - 7:14 pmRUT  Rutland-ORD Chicago O'Hare Intl
11h 09m1 stop Boston Logan Intl
$914Multiple 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 from Chicago O'Hare Intl Airport to Rutland 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 311 minutes over the past 3 months.

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

Cheapest flight

$265
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Rutland?

    Only Economy Class is available on flights from Chicago O'Hare Intl Airport to Rutland.

  • 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. Other layover airports each see under 5%.

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

    Yes. Being flexible with your travel dates can save you up to 28% on the Chicago O'Hare Intl Airport to Rutland route. 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.

  • 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 0h 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 $520 to $763. That means the highest observed fare was about 46% higher than the lowest one.

  • 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 can be flexible, aim for a Friday departure instead of Thursday. On this route, Friday flights average $374 - about $144 less than Thursday (28% savings) based on the last 12 months.

More options for your flight from Chicago to Rutland

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