$162 Cheap Flights from Rutland (RUT) to Chicago (ORD)

View $162 flight on Wed, Jan 7, 2026Opens in a new window

Popular airlines from Rutland, VT (RUT-Rutland Southern Vermont Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Rutland to Chicago (RUT-ORD)

Prices were available within the past 7 days and start at $162 for one-way flights and $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Nov 18 - Wed, Dec 3
RUT
Rutland
ORD
Chicago
$309 Roundtrip, found 4 days ago
$309
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Nov 18 from Rutland to Chicago, returning Wed, Dec 3, priced at $309 found 4 days ago
JetBlue Airways
Tue, Nov 18 - Sat, Nov 22
RUT
Rutland
ORD
Chicago
$314 Roundtrip, found 3 days ago
$314
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Nov 18 from Rutland to Chicago, returning Sat, Nov 22, priced at $314 found 3 days ago
JetBlue Airways
Mon, Nov 10 - Sat, Nov 22
RUT
Rutland
ORD
Chicago
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Nov 10 from Rutland to Chicago, returning Sat, Nov 22, priced at $319 found 4 days ago
JetBlue Airways
Wed, Nov 19 - Sat, Nov 22
RUT
Rutland
ORD
Chicago
$324 Roundtrip, found 3 days ago
$324
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Nov 19 from Rutland to Chicago, returning Sat, Nov 22, priced at $324 found 3 days ago
Cape Air
Tue, Oct 28 - Thu, Nov 13
RUT
Rutland
ORD
Chicago
$324 Roundtrip, found 4 days ago
$324
Roundtrip
found 4 days ago
Select Cape Air flight, departing Tue, Oct 28 from Rutland to Chicago, returning Thu, Nov 13, priced at $324 found 4 days ago
JetBlue Airways
Tue, Nov 4 - Tue, Nov 11
RUT
Rutland
ORD
Chicago
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Nov 4 from Rutland to Chicago, returning Tue, Nov 11, priced at $329 found 4 days ago
JetBlue Airways
Thu, Nov 20 - Sat, Nov 22
RUT
Rutland
ORD
Chicago
$334 Roundtrip, found 3 days ago
$334
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Nov 20 from Rutland to Chicago, returning Sat, Nov 22, priced at $334 found 3 days ago
Cape Air
Tue, Oct 28 - Wed, Nov 12
RUT
Rutland
ORD
Chicago
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select Cape Air flight, departing Tue, Oct 28 from Rutland to Chicago, returning Wed, Nov 12, priced at $334 found 4 days ago
JetBlue Airways
Tue, Oct 28 - Tue, Nov 11
RUT
Rutland
ORD
Chicago
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Oct 28 from Rutland to Chicago, returning Tue, Nov 11, priced at $339 found 4 days ago
Cape Air
Sat, Nov 22 - Thu, Nov 27
RUT
Rutland
ORD
Chicago
$339 Roundtrip, found 3 days ago
$339
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Nov 22 from Rutland to Chicago, returning Thu, Nov 27, priced at $339 found 3 days ago

Frequently asked questions

How much does a flight from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $162 or cheap return flight from $309 from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from RUT to ORD is November, when demand is low. Off-peak months are usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from RUT to ORD. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD)?
You'll need to book a flight with a layover if you're traveling from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, just filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from RUT to ORD?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) on schedule, book a flight that leaves from Rutland Southern Vermont Regional Airport (RUT) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book your flight from RUT to ORD generally means paying more. While you may come across some last-minute offers, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of landing a bargain.
Is it cheaper to book a RUT to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a RUT to ORD flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the hassle out of planning your trip. Just pick your flights and choose from our extensive range of stays, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Rutland Southern Vermont Regional Airport (RUT) to O'Hare Intl. Airport (ORD)?
If you reserved your RUT to ORD flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Travel information

Origin airport
Rutland Southern Vermont Regional
Destination airport
O'Hare Intl.
Airlines serving
JetBlue Airways
Roundtrip price
$308
Distance
765 mi

Book with confidence

Book with confidence

Rutland to Chicago Flights

The cheapest times to fly from Rutland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Rutland to Chicago are during the month of November. You can find some of the cheapest flights from Rutland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Rutland to Chicago

Sunday is one of the best days to book for cheap flights from Rutland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Rutland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Rutland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $162 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Rutland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Rutland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Rutland to Chicago Flights

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*Available to One Key members.