Cheap flights from Chicago (CHI) to New Windsor (SWF) from $97

Tuesday is generally a great day to depart. Flying on this day could help you save up to 4,928%.

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 39 days in advance, which can save you up to 43% on flights from Chicago to New Windsor compared to booking the week you need them. Waiting 39 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $263. For sooner than that we have options available in the next 3 days from $341.

The best pricing can be found in the month of February. Prices to New Windsor from Chicago average $244. You can even find prices in February for less than $244, as users have found deals to New Windsor from as low as $166. The month of June appears to be one of the more expensive times to travel to New Windsor from Chicago. Flying in the targeted month can save you up to 12%.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to New Windsor as you normally would.

Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to New Windsor from Chicago. Booking flights from Chicago to Stewart (SWF) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

Yes, there are multiple flights from Chicago to New Windsor for under $400. The cheapest flight booked recently is on Undisclosed Carrier for just $366, but on average you can expect to pay $599.

There are currently 1+ open flights from Chicago to New Windsor within the next 7 days for less than $500.

Cheapflights users have booked flights from Chicago to New Windsor round-trip from $366. Another airline that can offer you cheap pricing is Allegiant Air.

ORD and SWF are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to SWF refers to a flight route from Chicago O'Hare Intl Airport to New Windsor Stewart Airport. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).