$102 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 $102 One Way, $209 Round Trip from Chicago to Windham
Prices starting at $209 for return flights and $102 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
Portland Harbor Hotel
Dec 31 - Jan 4
Chicago (CHI) to Portland (PWM)
Reviewed on Nov 3, 2025
Cliff House Maine
Dec 25 - Dec 28
Chicago (ORD) to Portland (PWM)
Portland (PWM) to Chicago (ORD)
Reviewed on Aug 29, 2025
Inn By The Sea
Dec 31 - Jan 4
Chicago (CHI) to Portland (PWM)
Reviewed on Mar 28, 2022
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
Looking for cheap Chicago to Windham flights? Orbitz has the cheapest air fares for flights from Chicago to Windham. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.
Mobile Deals and Steals
Orbitz is dedicated to providing low fares on Chicago to Windham flights. Now you can find the latest deals on-the-go with Orbitz’s mobile apps for iPhone, iPad, Android phones, and tablets. Instantly see discounted rates for hotels, cruises, vacations, and air tickets for a great vacation.
Book Hotels With Confidence
When you’re looking for hotel rooms to go with your bargain flights from Chicago to Windham, Orbitz provides you descriptions, photos, reviews, and location maps so you know exactly what you are booking. With easy-to-use Orbitz map tools, you can search for nearby hotels on your mobile device.
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Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Chicago to Windham flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Chicago to Windham on your mobile device too, including delays and baggage claim details.
Cheap Air Ticket Prices Guaranteed
Orbitz is your number one source for low fares for Chicago to Windham flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Windham. Need hotels too? You can book them last minute on your mobile phone.
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Windham Airports
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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.