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Cheap flights from Rockland to Chicago from $278

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Rockland to Chicago departing on 6/27. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Rockland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:49 pm - 11:43 am
RKD
-
ORD
19h 54m
1 stop
Multiple Airlines Logo
9:41 pm - 6:37 pm
ORD
-
RKD
19h 56m
1 stop
$478Multiple Airlines
Tue, Jul 21 - Fri, Jul 24
JetBlue Logo
10:49 am - 9:58 pm
RKD
-
ORD
12h 09m
2 stops
JetBlue Logo
6:00 am - 8:13 pm
ORD
-
RKD
13h 13m
2 stops
$528JetBlue
Tue, Jul 21 - Fri, Jul 24
Multiple Airlines Logo
10:49 am - 7:25 pm
RKD
-
ORD
9h 36m
1 stop
Multiple Airlines Logo
6:00 am - 6:37 pm
ORD
-
RKD
11h 37m
2 stops
$533Multiple Airlines
Fri, Jul 3 - Tue, Jul 7
Multiple Airlines Logo
10:49 am - 7:25 pm
RKD
-
ORD
9h 36m
1 stop
Multiple Airlines Logo
10:56 am - 6:37 pm
ORD
-
RKD
6h 41m
1 stop
$546Multiple Airlines
Fri, Jul 3 - Tue, Jul 7
JetBlue Logo
7:00 am - 1:00 pm
RKD
-
ORD
7h 00m
1 stop
JetBlue Logo
1:09 pm - 8:13 pm
ORD
-
RKD
6h 04m
1 stop
$548JetBlue
Sat, Jul 4 - Sat, Jul 11
JetBlue Logo
7:00 am - 12:16 pm
RKD
-
ORD
6h 16m
1 stop
JetBlue Logo
10:56 am - 8:13 pm
ORD
-
RKD
8h 17m
1 stop
$574JetBlue
Sat, Jul 25 - Mon, Jul 27
JetBlue Logo
1:00 pm - 7:15 pm
RKD
-
ORD
7h 15m
1 stop
JetBlue Logo
10:56 am - 8:13 pm
ORD
-
RKD
8h 17m
1 stop
$614JetBlue
Fri, Jul 24 - Mon, Jul 27
JetBlue Logo
1:00 pm - 7:15 pm
RKD
-
ORD
7h 15m
1 stop
JetBlue Logo
10:56 am - 8:13 pm
ORD
-
RKD
8h 17m
1 stop
$638JetBlue
Thu, Jul 23 - Mon, Jul 27
JetBlue Logo
10:49 am - 7:15 pm
RKD
-
ORD
9h 26m
1 stop
JetBlue Logo
10:56 am - 8:13 pm
ORD
-
RKD
8h 17m
1 stop
$644JetBlue
Wed, Jul 22 - Thu, Jul 23
JetBlue Logo
1:00 pm - 7:15 pm
RKD
-
ORD
7h 15m
1 stop
JetBlue Logo
10:56 am - 8:13 pm
ORD
-
RKD
8h 17m
1 stop
$732JetBlue
Thu, Jul 16 - Thu, Jul 23

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JetBlue flights from Rockland to Chicago

Our best JetBlue deals on Rockland to Chicago flight tickets
JetBlue
Jul 4
RKD7:00 amRockland Knox County Regional
7h 00m
1 stop
ORD1:00 pmChicago O'Hare Intl
Jul 11
ORD1:09 pmChicago O'Hare Intl
6h 04m
1 stop
RKD8:13 pmRockland Knox County Regional
$548
JetBlue
Jul 25
RKD7:00 amRockland Knox County Regional
6h 16m
1 stop
ORD12:16 pmChicago O'Hare Intl
Jul 27
ORD10:56 amChicago O'Hare Intl
8h 17m
1 stop
RKD8:13 pmRockland Knox County Regional
$574
JetBlue
Jul 1
RKD1:00 pmRockland Knox County Regional
7h 25m
1 stop
ORD7:25 pmChicago O'Hare Intl
Jul 3
ORD10:56 amChicago O'Hare Intl
8h 17m
1 stop
RKD8:13 pmRockland Knox County Regional
$604

momondo Fare Finder

 
Customize your flight search to find flights from Rockland to Chicago 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 June 23, 2026.
Use the filters below to find and compare flights from Rockland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Tue 7/21

4:49 pm-11:43 am

1 stop19h 54m

Chicago O'Hare Intl

Fri 7/24

9:41 pm-6:37 pm

1 stop19h 56m

$478

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Tue 7/21

10:49 am-9:58 pm

2 stops12h 09m

Chicago O'Hare Intl

Fri 7/24

6:00 am-8:13 pm

2 stops13h 13m

$528

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Fri 7/3

10:49 am-7:25 pm

1 stop9h 36m

Chicago O'Hare Intl

Tue 7/7

6:00 am-6:37 pm

2 stops11h 37m

$533

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Fri 7/3

10:49 am-7:25 pm

1 stop9h 36m

Chicago O'Hare Intl

Tue 7/7

10:56 am-6:37 pm

1 stop6h 41m

$546
Quickest round-trip

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Sat 7/4

7:00 am-1:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Sat 7/11

1:09 pm-8:13 pm

1 stop6h 04m

$548

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Sat 7/25

7:00 am-12:16 pm

1 stop6h 16m

Chicago O'Hare Intl

Mon 7/27

10:56 am-8:13 pm

1 stop8h 17m

$574

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Fri 7/24

1:00 pm-7:15 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 7/27

10:56 am-8:13 pm

1 stop8h 17m

$614

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Thu 7/23

1:00 pm-7:15 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 7/27

10:56 am-8:13 pm

1 stop8h 17m

$638

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Wed 7/22

10:49 am-7:15 pm

1 stop9h 26m

Chicago O'Hare Intl

Thu 7/23

10:56 am-8:13 pm

1 stop8h 17m

$644

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Thu 7/16

1:00 pm-7:15 pm

1 stop7h 15m

Chicago O'Hare Intl

Thu 7/23

10:56 am-8:13 pm

1 stop8h 17m

$732

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Rockland to Chicago

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 Rockland Knox County Regional to Chicago?

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

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Rockland according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Rockland to Chicago

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

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

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

Fastest flight time

7h 31m

Direct flights

None
The fastest flight from Rockland to Chicago takes 7h 31m
There are no direct flights from Rockland to Chicago. There are no popular flight routes from Rockland to Chicago.
Search flight deals

Frequently asked questions about flying from Rockland to Chicago

  • How far is Rockland Knox County Regional to Chicago by plane?

    The straight-line distance from Rockland Knox County Regional to Chicago is 945.8 mi. By plane, this route typically takes 7h 31m.

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

    Prices for flights from Rockland Knox County Regional Airport to Chicago were last updated today.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Rockland Knox County Regional Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Rockland.

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

Yes. All flights to Chicago from Rockland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Chicago from Rockland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Chicago from Rockland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport