$83 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 $83 One Way, $156 Round Trip from Chicago to Gloucester
Prices starting at $156 for return flights and $83 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 Beverly
Oct 3 - Oct 6
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 13, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Sep 19 - Sep 26
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Jul 27, 2026
Gloucester packages with premium economy flights
The Langham, Boston
Oct 1 - Oct 4
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 13, 2026
Raffles Boston
Oct 1 - Oct 4
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 14, 2026
Gloucester first class flight packages
The Godfrey Hotel Boston
Oct 6 - Oct 13
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 14, 2026
The Newbury Boston
Oct 6 - Oct 13
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 13, 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 combines guaranteed low prices with cutting-edge mobile tools for travel from Chicago to Gloucester to give you a travel experience that is second to none.
Bargain Travel at Your Fingertips
Orbitz provides the cheapest fares from Chicago to Gloucester. When reserving your flight you can mix and match a range of low cost airlines for you departing and returning domestic or international flights. This way you can travel on a budget while selecting the flights that suit your schedule.
Modern Tools for Fast-Paced Travel
Orbitz makes use of the latest technology to ensure that you are always kept up-to-date on the status of your Chicago to Gloucester flights. Through easy-to-use mobile Android and iPhone apps you can book low cost flights from Chicago to Gloucester and choose a range of cheap hotels to stay in.
Enjoy Stress-Free Travel with Flight Alerts
Once you have booked your flights from Chicago to Gloucester on Orbitz you will always be kept informed of any changes to your flight. When you opt into Orbitz’s free email and SMS alerts on your Chicago to Gloucester flights you can ask Orbitz to send the flight details to up to 6 other contacts, so keeping your family and business team informed is a cinch.
Frequent Flyer Program
For loyal Orbitz customers who fly from Chicago to Gloucester the chance to join our frequent flyer program is an added bonus. Simply log-on to your online account and input your frequent flyer number for future 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.