Cheap flights from Chicago to Rockland from $469

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Rockland departing on 12/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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JetBlue Logo
11:25 am - 7:20 pmORD-RKD
6h 55m1 stop
JetBlue Logo
10:15 am - 6:46 pmRKD-ORD
9h 31m1 stop
$469JetBlue
Find Deal
Thu, Dec 11 - Thu, Dec 18
JetBlue Logo
10:08 am - 7:20 pmORD-RKD
8h 12m1 stop
JetBlue Logo
10:15 am - 6:18 pmRKD-ORD
9h 03m1 stop
$724JetBlue
Find Deal
Sun, Oct 19 - Thu, Oct 23
JetBlue Logo
10:08 am - 6:01 pmORD-RKD
6h 53m1 stop
JetBlue Logo
10:15 am - 6:18 pmRKD-ORD
9h 03m1 stop
$764JetBlue
Find Deal
Tue, Oct 14 - Fri, Oct 17

JetBlue flights from Chicago to Rockland

Our best JetBlue deals on Chicago to Rockland flight tickets
JetBlue
Dec 11
ORD11:25 amChicago O'Hare Intl
6h 55m
1 stop
RKD7:20 pmRockland Knox County Regional
Dec 18
RKD10:15 amRockland Knox County Regional
9h 31m
1 stop
ORD6:46 pmChicago O'Hare Intl
JetBlue
Oct 19
ORD10:08 amChicago O'Hare Intl
8h 12m
1 stop
RKD7:20 pmRockland Knox County Regional
Oct 23
RKD10:15 amRockland Knox County Regional
9h 03m
1 stop
ORD6:18 pmChicago O'Hare Intl
JetBlue
Oct 14
ORD10:08 amChicago O'Hare Intl
6h 53m
1 stop
RKD6:01 pmRockland Knox County Regional
Oct 17
RKD10:15 amRockland Knox County Regional
9h 03m
1 stop
ORD6:18 pmChicago O'Hare Intl

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Rockland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 2, 2025.
Use the filters below to find and compare flights from Chicago to Rockland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Thu 12/11

11:25 am-7:20 pm

1 stop6h 55m

Rockland Knox County Regional

Thu 12/18

10:15 am-6:46 pm

1 stop9h 31m

$469

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Sun 10/19

10:08 am-7:20 pm

1 stop8h 12m

Rockland Knox County Regional

Thu 10/23

10:15 am-6:18 pm

1 stop9h 03m

$724

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Tue 10/14

10:08 am-6:01 pm

1 stop6h 53m

Rockland Knox County Regional

Fri 10/17

10:15 am-6:18 pm

1 stop9h 03m

$764

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Chicago to Rockland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to Rockland?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Rockland from Chicago according to our data. United Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Rockland. Keep in mind that there are 4 different airlines that fly to Rockland on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to Rockland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Rockland according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Rockland (CHI to RKD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Rockland

Direct flights

None
There are no direct flights from Chicago to Rockland. There are no popular flight routes from Chicago to Rockland.
  • How far is Chicago to Rockland Knox County Regional by plane?

    The distance between Chicago and Rockland Knox County Regional is about 945.8 mi. Flights usually cover this in 6h 53m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Rockland Knox County Regional Airport?

    Prices for flights from Chicago to Rockland Knox County Regional Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago to Rockland Knox County Regional Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Rockland Knox County Regional Airport.

  • What documentation or ID do you need to fly to Rockland Knox County Regional Airport?

    The required travel and health documents for your Rockland Knox County Regional Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Rockland Knox County Regional Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Rockland?

Book flights to Rockland if you plan to visit one of these locations
Camden
Rockport

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Rockland?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Rockland. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Rockland with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Rockland from Chicago with this policy.

How can momondo help me find flights from Chicago to Rockland?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Rockland from Chicago.

I’m not ready to book a flight from Chicago to Rockland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Rockland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Rockland and let you know when they change.

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1 adult
Sat 11/1
Sat 11/8

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