
$115 Cheap flight deals from Chicago (CHI) to Kennebunk (PWM)
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This Weekend's Flight Deals from Chicago to Kennebunk
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 $115 One Way, $209 Round Trip from Chicago to Kennebunk
Prices starting at $209 for return flights and $115 for one-way flights to Kennebunk were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Kennebunk economy flight packages

Portland Harbor Hotel
Feb 12 - Feb 15
Chicago (CHI) to Portland (PWM)
Reviewed on Dec 8, 2025

Inn By The Sea
Feb 12 - Feb 15
Chicago (CHI) to Portland (PWM)
Reviewed on Mar 28, 2022

Portland Regency Hotel & Spa
Feb 12 - Feb 15
Chicago (CHI) to Portland (PWM)
Reviewed on Sep 12, 2025
More About Flying To Kennebunk from Chicago
Route Information for Flights from Chicago to Kennebunk
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | PWM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Kennebunk
Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for Chicago to Kennebunk flights at low cost, you will not be disappointed.
Cruising for a bargain deal
Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from Chicago to Kennebunk so you can reach your destination with more money in your pocket to spend.
Cheap Chicago to Kennebunk flights that lead to rewards
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Quality combinations
If you require budget Chicago to Kennebunk flights and a bargain hotel to go with it, Orbitz will wow you with the great combinations we can offer. The quality is always high and always a superb value.
Even last minute bookings on our apps
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Flights from Chicago
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Kennebunk 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.


