$100 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 $100 One Way, $186 Round Trip from Chicago to Gloucester
Prices starting at $186 for return flights and $100 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
Sep 29 - Oct 2
Chicago (ORD) to Boston (BOS)
Reviewed on Jun 8, 2026
Good Hotels Boston
Sep 26 - Sep 30
Chicago (CHI) to Boston (BOS)
Reviewed on May 23, 2026
The Langham, Boston
Oct 2 - Oct 5
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 6, 2026
Gloucester packages with premium economy flights
Arcadian Hotel
Sep 24 - Sep 27
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 7, 2026
The Charles Hotel
Sep 24 - Sep 27
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Battery Wharf Hotel, Boston Waterfront
Sep 24 - Sep 27
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 7, 2026
Gloucester first class flight packages
The Whitney Hotel
Sep 11 - Sep 13
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 6, 2026
Chatham Tides
Sep 20 - Sep 24
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 5, 2026
More About Flying To Gloucester from Chicago
Route Information for Flights from Chicago to Gloucester
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Gloucester
Orbitz guarantees you low prices on flights from Chicago to Gloucester. In addition to low fares on Chicago to Gloucester flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.
Earn Miles While Saving
Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Chicago to Gloucester. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Chicago to Gloucester flights.
Travel Planning Made Easy
We help take some of the anxiety out of your Chicago to Gloucester flights with free flight alerts. We will let you know of flight changes and delays to your flights from Chicago to Gloucester by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.
Use Mobile Apps with Orbitz
Orbitz lets you find the best deals on Chicago to Gloucester flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.
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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.