
$97 Cheap flight deals from Chicago (CHI) to Westbrook (PWM)
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This Weekend's Flight Deals from Chicago to Westbrook
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 $97 One Way, $213 Round Trip from Chicago to Westbrook
Prices starting at $213 for return flights and $97 for one-way flights to Westbrook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Westbrook economy flight packages

Hilton Garden Inn Portland Airport
Dec 25 - Dec 31
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Nov 8, 2025

Portland Harbor Hotel
Dec 25 - Dec 31
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Nov 3, 2025

Inn By The Sea
Dec 25 - Dec 31
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Mar 28, 2022
More About Flying To Westbrook from Chicago
Route Information for Flights from Chicago to Westbrook
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | PWM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Westbrook
The best fares for Chicago to Westbrook flights are always found on Orbitz. With superior discounts and the latest innovations in mobile access, your ideal trip starts with Orbitz.
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Westbrook 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.

