$104 Cheap flight deals from Chicago (CHI) to Windham (PWM)
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This Weekend's Flight Deals from Chicago to Windham
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $104 One Way, $228 Round Trip from Chicago to Windham
Prices starting at $228 for return flights and $104 for one-way flights to Windham were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Windham economy flight packages
Ogunquit River Inn & Suites
May 4 - May 8
Chicago (ORD) to Portland (PWM)
Reviewed on Sep 14, 2025
Portland Harbor Hotel
May 10 - May 15
Chicago (CHI) to Portland (PWM)
Reviewed on Dec 8, 2025
The Docent's Collection at 121 Middle Street
May 10 - May 15
Chicago (CHI) to Portland (PWM)
Reviewed on Mar 10, 2023
More About Flying To Windham from Chicago
Route Information for Flights from Chicago to Windham
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | PWM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Windham
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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.