
$154 Cheap flight deals from Chicago (CHI) to Wolfeboro (PWM)
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This Weekend's Flight Deals from Chicago to Wolfeboro
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, $292 Round Trip from Chicago to Wolfeboro
Prices starting at $292 for return flights and $154 for one-way flights to Wolfeboro were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wolfeboro economy flight packages

Saco Bay Hotel
Jun 23 - Jun 27
Chicago (CHI) to Portland (PWM)
Reviewed on May 9, 2026

Ogunquit River Inn & Suites
Jun 23 - Jun 27
Chicago (CHI) to Portland (PWM)
Reviewed on Sep 14, 2025

Cliff House Maine
Jul 5 - Jul 10
Chicago (ORD) to Portland (PWM)
Reviewed on Aug 29, 2025
Wolfeboro first class flight packages

The Docent's Collection at 121 Middle Street
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Mar 31, 2026

Portland Harbor Hotel
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Dec 8, 2025

Canopy by Hilton Portland Waterfront
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Aug 25, 2025
More About Flying To Wolfeboro from Chicago
Route Information for Flights from Chicago to Wolfeboro
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | PWM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Wolfeboro
The best fares for Chicago to Wolfeboro 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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We provide access to many low-cost vacation packages and travelers can mix and match airlines when scheduling their flights for the best prices and flight times. Finding cheap tickets on flights from Chicago to Wolfeboro is easy when you make Orbitz your #1 travel planner.
Book Chicago to Wolfeboro Flights With Mobile Apps
Our iPhone and Android mobile apps can be used to compare and book flights from Chicago to Wolfeboro. These apps are perfect for checking the status of flights, gate and baggage claims details, car rental rates, and for receiving alerts on special savings that are exclusive to mobile users. Mobile app users can even score great rates when booking hotel rooms. You can compare hotels, virtually view photo galleries, and check out user reviews using the app, as well as find out which ones are closest to you.
Orbitz also offers free travel updates that are sent to your email or mobile phone that notifies you of booking changes, disruptions in service, or delayed flights.
Increase Your Rewards While Enjoying Super Low Rates
Boost your points or miles for your frequent flyer program on certain Chicago to Wolfeboro flights. Simply provide your frequent flyer information when booking flights from Chicago to Wolfeboro with Orbitz and get both a low fare and travel rewards. You can enter this information in your Orbitz account profile for easy remembering in future bookings.
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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.


