$108 Cheap flight deals from Chicago (CHI) to Windham (PWM)
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Airfares from $108 One Way, $213 Round Trip from Chicago to Windham
Prices starting at $213 for return flights and $108 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 Regency Hotel & Spa
May 15 - May 18
Chicago (ORD) to Portland (PWM)
Reviewed on Sep 12, 2025
Kennebunkport Captains Collection
May 15 - May 18
Chicago (ORD) to Portland (PWM)
Reviewed on Oct 7, 2024
Inn By The Sea
May 11 - May 13
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
Great Deals on Flights From Chicago to Windham
Spend more of your time and money at Windham instead of sitting at your computer, searching for discount Chicago to Windham flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Windham.
Flights That Fit Your Budget
Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Windham flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.
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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.