Cheap flights from Rockland to Chicago from $424

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Rockland to Chicago departing on 1/23. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Rockland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
10:45 am - 5:43 pmRKD-ORD
7h 58m1 stop
JetBlue Logo
7:45 am - 2:51 pmORD-RKD
6h 06m1 stop
$424JetBlue
Find Deal
Fri, Jan 23 - Sun, Jan 25

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 December 1, 2025.
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

RocklandChicago

RKD - ORD

RKDORD

Rockland Knox County Regional

Fri 1/23

10:45 am-5:43 pm

1 stop7h 58m

Chicago O'Hare Intl

Sun 1/25

7:45 am-2:51 pm

1 stop6h 06m

$424

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 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 56% 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

9h 58m

Direct flights

None
The fastest flight from Rockland to Chicago takes 9h 58m
There are no direct flights from Rockland to Chicago. There are no popular flight routes 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 58m.

  • 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 12/31
Wed 1/7

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