$109 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 $109 One Way, $198 Round Trip from Chicago to Gloucester
Prices starting at $198 for return flights and $109 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
The Cove at Yarmouth by Westgate Resorts
Oct 8 - Oct 12
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jun 8, 2026
Fairmont Copley Plaza, Boston
Oct 9 - Oct 12
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Colonial Acres Resort
Oct 8 - Oct 12
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Gloucester first class flight packages
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
It has never been easier to find cheap Chicago to Gloucester flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
Plan Your Chicago to Gloucester Flights on the Go
Orbitz offers cutting-edge mobile tools that let you search and book flights anywhere. All you need is a smartphone or mobile device to find discounts on flights from Chicago to Gloucester. Use the app to check to make sure your flight is on time or book a last-minute cheap hotel room.
Get the Best Deals on Chicago to Gloucester Flights
Finding great deals on flights from Chicago to Gloucester is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Gloucester vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Gloucester flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.
Flight Alerts Keep You Informed
Stay on top of the latest updates for flights from Chicago to Gloucester. We send you free email and mobile alerts to keep you informed about delays to Chicago to Gloucester flights.
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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.