
$47 Cheap flight deals from Chicago (CHI) to Gloucester (BOS)
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This Weekend's Flight Deals from Chicago to Gloucester
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 $47 One Way, $106 Round Trip from Chicago to Gloucester
Prices starting at $106 for return flights and $47 for one-way flights to Gloucester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Gloucester economy flight packages

Sunbird ANNEX Resort
Jun 20 - Jun 23
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 4, 2019

Riverview Resort
Jun 13 - Jun 16
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jun 17, 2019

Lighthouse Inn
Jun 13 - Jun 16
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Aug 20, 2024
Gloucester first class flight packages

Anchorage Inn and Resort
Jun 8 - Jun 13
Chicago (MDW) to Boston (BOS)
Reviewed on Jan 13, 2025

More About Flying To Gloucester from Chicago
Route Information for Flights from Chicago to Gloucester
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Gloucester
For the best travel experience from Chicago to Gloucester domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.
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Earn Rewards on Your Chicago to Gloucester Flights
At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of Chicago to Gloucester flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.
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Gloucester 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.