$297 Cheap Flights from Chicago (ORD) to Rockland (RKD)

View $297 flight on Mon, Dec 22, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Rockland, ME (RKD-Knox County Regional)

Cheap Flights from Chicago to Rockland (ORD-RKD)

Prices were available within the past 7 days and start at $297 for one-way flights and $490 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Sat, Nov 8 - Tue, Nov 11
ORD
Chicago
RKD
Rockland
$490 Roundtrip, found 5 days ago
$490
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Nov 8 from Chicago to Rockland, returning Tue, Nov 11, priced at $490 found 5 days ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD) cost?
Secure a cheap one-way flight from $297 or cheap return flight from $490 from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD) 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 O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD)?
Planning your trip for November can help you save, as it's the cheapest month for flights between ORD and RKD. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest ORD to RKD flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD)?
Direct flights from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to RKD?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* But this can vary depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD) route, travel before 3 PM. Flights after this time are 22% more likely to be canceled.**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 O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD) last-minute?
Last-minute bookings from ORD to RKD are typically more expensive. To secure the lowest rates, start searching for flights ahead of time. That being said, if you're flexible with your travel plans, you may score a cheap ticket right before your journey.
Is it cheaper to book an ORD to RKD flight and hotel package?
Booking an ORD to RKD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Knox County Regional Airport (RKD)?
Generally, it's possible to cancel or reschedule your ORD to RKD flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Knox County Regional
Roundtrip price
$489
Distance
958 mi

Book with confidence

Chicago to Rockland Flights

The cheapest times to fly from Chicago to Rockland

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 Chicago to Rockland are during the month of November. You can find some of the cheapest flights from Chicago to Rockland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Rockland

Sunday is one of the best days to book for cheap flights from Chicago to Rockland: 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 Chicago to Rockland

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 Chicago to Rockland in 2025. You can also book with separate airlines for your outbound and return journeys, from $297 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 Chicago to Rockland 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 Chicago to Rockland 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.

 

Chicago to Rockland Flights

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*Available to One Key members.