
$154 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 $154 One Way, $297 Round Trip from Chicago to Westbrook
Prices starting at $297 for return flights and $154 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

Saco Bay Hotel
Jun 13 - Jun 20
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on May 9, 2026

Ogunquit River Inn & Suites
Jun 13 - Jun 20
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Sep 14, 2025

The Meadowmere Resort
Jun 19 - Jun 23
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Aug 5, 2025
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
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You can always find affordable flights from Chicago to Westbrook on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.
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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.



