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Flight 2.

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The cheapest way to get from Rockland to Chicago costs only, and the quickest way takes just 5 hours. Find the travel option that best suits you. How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Rockland? KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Rockland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.