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Cheap flights from Chicago to Rockland from $337

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Rockland departing on 8/13. 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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Cheap round-trip flights

JetBlue Logo
9:42 am - 3:28 pmORD-RKD
4h 46m1 stop
JetBlue Logo
11:14 am - 6:55 pmRKD-ORD
8h 41m1 stop
$574JetBlue
Find Deal
Wed, Sep 3 - Mon, Sep 8
JetBlue Logo
9:42 am - 6:01 pmORD-RKD
7h 19m1 stop
JetBlue Logo
11:14 am - 6:55 pmRKD-ORD
8h 41m1 stop
$584JetBlue
Find Deal
Fri, Sep 5 - Mon, Sep 8
JetBlue Logo
8:40 am - 6:01 pmORD-RKD
8h 21m1 stop
JetBlue Logo
10:53 am - 3:29 pmRKD-ORD
5h 36m1 stop
$604JetBlue
Find Deal
Mon, Aug 18 - Fri, Aug 22
JetBlue Logo
9:51 am - 6:01 pmORD-RKD
7h 10m1 stop
JetBlue Logo
11:14 am - 6:55 pmRKD-ORD
8h 41m1 stop
$614JetBlue
Find Deal
Sat, Sep 6 - Thu, Sep 11
JetBlue Logo
9:42 am - 3:28 pmORD-RKD
4h 46m1 stop
JetBlue Logo
11:14 am - 5:55 pmRKD-ORD
7h 41m1 stop
$624JetBlue
Find Deal
Mon, Oct 6 - Tue, Oct 7
JetBlue Logo
8:40 am - 3:28 pmORD-RKD
5h 48m1 stop
JetBlue Logo
11:14 am - 5:54 pmRKD-ORD
7h 40m1 stop
$644JetBlue
Find Deal
Tue, Sep 2 - Fri, Sep 5
Logo
5:16 pm - 3:28 pmORD-RKD
21h 12m2 stops
Logo
10:53 am - 10:22 pmRKD-ORD
12h 29m2 stops
$649
Find Deal
Thu, Aug 14 - Mon, Aug 18
JetBlue Logo
9:51 am - 6:01 pmORD-RKD
7h 10m1 stop
JetBlue Logo
11:14 am - 5:55 pmRKD-ORD
7h 41m1 stop
$659JetBlue
Find Deal
Fri, Oct 3 - Tue, Oct 7
JetBlue Logo
9:42 am - 6:01 pmORD-RKD
7h 19m1 stop
JetBlue Logo
11:14 am - 5:55 pmRKD-ORD
7h 41m1 stop
$664JetBlue
Find Deal
Mon, Oct 6 - Wed, Oct 8
Logo
12:05 pm - 2:03 pmORD-RKD
24h 58m3 stops
Logo
10:53 am - 10:22 pmRKD-ORD
12h 29m2 stops
$682
Find Deal
Thu, Aug 14 - Mon, Aug 18

JetBlue flights from Chicago to Rockland

Our best JetBlue deals on Chicago to Rockland flight tickets
JetBlue
Sep 3
ORD9:42 amChicago O'Hare Intl
4h 46m
1 stop
RKD3:28 pmRockland Knox County Regional
Sep 8
RKD11:14 amRockland Knox County Regional
8h 41m
1 stop
ORD6:55 pmChicago O'Hare Intl
$574
Find similar
JetBlue
Sep 5
ORD9:42 amChicago O'Hare Intl
7h 19m
1 stop
RKD6:01 pmRockland Knox County Regional
Sep 8
RKD11:14 amRockland Knox County Regional
8h 41m
1 stop
ORD6:55 pmChicago O'Hare Intl
$584
Find similar
JetBlue
Aug 18
ORD8:40 amChicago O'Hare Intl
8h 21m
1 stop
RKD6:01 pmRockland Knox County Regional
Aug 22
RKD10:53 amRockland Knox County Regional
5h 36m
1 stop
ORD3:29 pmChicago O'Hare Intl
$604
Find similar

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 July 31, 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

Wed 9/3

9:42 am-3:28 pm

1 stop4h 46m

Rockland Knox County Regional

Mon 9/8

11:14 am-6:55 pm

1 stop8h 41m

$574

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Fri 9/5

9:42 am-6:01 pm

1 stop7h 19m

Rockland Knox County Regional

Mon 9/8

11:14 am-6:55 pm

1 stop8h 41m

$584

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Mon 8/18

8:40 am-6:01 pm

1 stop8h 21m

Rockland Knox County Regional

Fri 8/22

10:53 am-3:29 pm

1 stop5h 36m

$604

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Sat 9/6

9:51 am-6:01 pm

1 stop7h 10m

Rockland Knox County Regional

Thu 9/11

11:14 am-6:55 pm

1 stop8h 41m

$614

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Mon 10/6

9:42 am-3:28 pm

1 stop4h 46m

Rockland Knox County Regional

Tue 10/7

11:14 am-5:55 pm

1 stop7h 41m

$624

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Tue 9/2

8:40 am-3:28 pm

1 stop5h 48m

Rockland Knox County Regional

Fri 9/5

11:14 am-5:54 pm

1 stop7h 40m

$644

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Thu 8/14

5:16 pm-3:28 pm

2 stops21h 12m

Rockland Knox County Regional

Mon 8/18

10:53 am-10:22 pm

2 stops12h 29m

$649

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Fri 10/3

9:51 am-6:01 pm

1 stop7h 10m

Rockland Knox County Regional

Tue 10/7

11:14 am-5:55 pm

1 stop7h 41m

$659

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Mon 10/6

9:42 am-6:01 pm

1 stop7h 19m

Rockland Knox County Regional

Wed 10/8

11:14 am-5:55 pm

1 stop7h 41m

$664

ChicagoRockland

ORD - RKD

ORDRKD

Chicago O'Hare Intl

Thu 8/14

12:05 pm-2:03 pm

3 stops24h 58m

Rockland Knox County Regional

Mon 8/18

10:53 am-10:22 pm

2 stops12h 29m

$682

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Rockland from

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 is the cheapest airline that flies from Chicago to Rockland Knox County Regional?

JetBlue is the most popular carrier operating from Chicago to Rockland Knox County Regional

What airlines fly to Rockland?

United Airlines, American Airlines and Southwest 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 56% of people opting to fly with this airline when traveling to Rockland. Keep in mind that there are 5 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

Best Price Found

$337

Fastest flight time

4h 46m

Direct flights

None

Airports in Rockland

1 airport
The best one-way flight to Rockland from Chicago in the past 72 hours is $337. The best round-trip flight deal from Chicago to Rockland found on momondo in the last 72 hours is $574.
The fastest flight from Chicago to Rockland takes 4h 46m
There are no direct flights from Chicago to Rockland. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Rockland Knox County Regional Airport.
There is 1 airport near Rockland: Rockland Knox County Regional (RKD)
Search flight deals

  • 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 4h 46m, 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.

An easier way to manage your Rockland trip

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