Cheap flight deals from Chicago (CHI) to Pawling (SWF)
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Pawling economy flight packages
Night Hotel Broadway
May 7 - May 10
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Reviewed on Nov 28, 2025
Hotel St. James
May 7 - May 10
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Reviewed on Mar 28, 2026
1 Hotel Brooklyn Bridge
May 15 - May 17
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Reviewed on Feb 21, 2023
Pawling packages with premium economy flights
Hilton Garden Inn Long Island City New York
May 19 - May 26
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Reviewed on Aug 29, 2025
Hotel St. James
May 19 - May 26
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Reviewed on Mar 28, 2026
Margaritaville Resort Times Square
May 19 - May 26
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Reviewed on Mar 30, 2026
Pawling first class flight packages
Night Hotel Broadway
May 24 - May 30
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Reviewed on Nov 28, 2025
Hotel St. James
May 24 - May 30
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Reviewed on Mar 28, 2026
Hotel Riu Plaza New York Times Square
May 24 - May 30
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Reviewed on Feb 7, 2026
More About Flying To Pawling from Chicago
Route Information for Flights from Chicago to Pawling
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SWF |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Pawling
Orbitz guarantees you low prices on flights from Chicago to Pawling. In addition to low fares on Chicago to Pawling flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.
Earn Miles While Saving
Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Chicago to Pawling. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Chicago to Pawling flights.
Travel Planning Made Easy
We help take some of the anxiety out of your Chicago to Pawling flights with free flight alerts. We will let you know of flight changes and delays to your flights from Chicago to Pawling by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.