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Flights from Chicago to Rockland
There are no direct flights from Chicago to Rockland. The fastest way is one stop via Boston or Westchester County, about 5h 19m door to door (38 connections a week on current schedules).
No direct flights · 2 connection options From 5h 19m
Chicago to Rockland at a glance
Fastest journey5h 19mVia Boston, on current schedules
Nonstop flightsNoneConnect via Boston or Westchester County
Best ways to fly from Chicago to Rockland
Ranked by how easy the connection is: one airline or alliance first (bags and connection protected), then the quickest self-transfer options.
1Search
CHI Boston (BOS) RKD
Leg 1: American Airlines, Delta Air Lines, JetBlue Airways · Leg 2: Cape Air
Thu10:00 CHI13:03 BOS2h 12m connection15:15 BOS16:19 RKDJetBlue Airways + Cape Air
Connections are computed from flights actually flown over the last 8 weeks, with at least 45 minutes to change on one airline and 2 hours on separate tickets. Times are local. The search shows live itineraries and exact times.
Good to know
- Distance
- 1,524 km946 miles
- Journey time
- 5h 19mon current schedules
- Time difference
- +1hRockland vs Chicago
- Currency in Rockland
- USD
- Airports
- ORD, MDW, RFD → RKD
Flights from Chicago to Rockland: questions answered
Are there direct flights from Chicago to Rockland?
No. There is no nonstop service, so you will connect, most easily in Boston and Westchester County. Most connections mean separate tickets, so leave plenty of time to collect bags and check in again.
How long is the flight from Chicago to Rockland?
With one connection the journey usually takes around 5h 19m, depending on the layover. The straight-line distance is 1,524 km.
Where do you change planes between Chicago and Rockland?
The best connecting points are Boston (BOS) and Westchester County (HPN). Compare one-ticket itineraries with self-transfer options in the search.
Which airports serve Chicago and Rockland?
Chicago: Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW) and Chicago Rockford International Airport (RFD). Rockland: Knox County Regional Airport (RKD).
What is the time difference between Chicago and Rockland?
Rockland is 1 hour ahead of Chicago.
