Flights From Chicago (CHI) to Gloucester (BOS)
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
Selected fares from Chicago to Gloucester
The cheapest prices found with in the last 7 days for return flights were CA $190 and CA $95 for one-way flights to Gloucester for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Apr 3 - Wed, Apr 8
ORD
O'Hare Intl.
BOS
Logan Intl.
CA $190 Roundtrip, found 2 days ago
CA $190
Roundtrip
found 2 days ago
Sat, May 2 - Sat, May 9
ORD
O'Hare Intl.
BOS
Logan Intl.
CA $193 Roundtrip, found 3 days ago
CA $193
Roundtrip
found 3 days ago
Wed, Apr 29 - Mon, May 4
ORD
O'Hare Intl.
BOS
Logan Intl.
CA $228 Roundtrip, found 2 days ago
CA $228
Roundtrip
found 2 days ago
More to explore for Chicago to Gloucester
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in Gloucester
- Cottages in Beverly
- Beverly Hotels
- Hotels near Bewitched in Salem
- Essex Hotels
- Apartments in Gloucester
- B&B in Gloucester
- Cottages in Gloucester
- Beach Resorts & in Gloucester
- Convention Center Hotels in Gloucester
- Kid Friendly Hotels in Gloucester
- Golf Resorts & in Gloucester
- Luxury Hotels in Gloucester
- Pet Friendly Hotels in Gloucester
- Spa Resorts & in Gloucester
- Hotel Wedding Venues Hotels in Gloucester
- Gloucester Hotels
- Motels in Gloucester
- Vacation Homes in Gloucester
- Resorts in Gloucester
- Hotels near Good Harbor Beach
- Hotels near Greenwood Farm
- Hamilton Hotels
- Ipswich Hotels
- Magnolia Hotels
- B&B in Manchester-by-the-Sea
- Cottages in North Shore
- B&B in Rockport
- Beach Resorts & in Rockport
- Spa Resorts & in Rockport
- Rockport Hotels
- Vacation Homes in Rockport
- Rowley Hotels
- B&B in Salem
- Condos in Salem
- Cottages in Salem
- Extended Stay Hotels in Salem
- Hostels in Salem
- Beach Resorts & in Salem
- Boutique Hotels in Salem
- Kid Friendly Hotels in Salem
- Four Seasons Hotels in Salem
- Highgate Independent Hotels in Salem
- Historic Hotels in Salem
- Luxury Hotels in Salem
- Pet Friendly Hotels in Salem
- Hotel Wedding Venues Hotels in Salem
- Salem Hotels
- Houseboat Rentals in Salem
- Motels in Salem
- Vacation Homes in Salem
- Hotels near Salem Witch Museum
- Hotels near Salem Witch Trials Memorial
- Hotels near Wingaersheek Beach
- Flights to Gloucester
- Flights to Peabody
- Flights to Salem
- Flights from Atlanta to Gloucester
- Flights from Cleveland to Salem
- Flights from Montreal to Salem
- Flights from Orlando to West Newbury
- Flights from Santiago to Salem
- Flights from Vancouver to Salem
- Flights from Vancouver to Gloucester
- Flights from Milwaukee to Salem
- Flights from Porto to Salem
- Flights from Port-au-Prince to Gloucester
- Flights from Bengaluru to Salem
- Flights from Winnipeg to Salem
- Flights from Atlanta (ATL) to Boston (BOS)
- Flights from Hartford (BDL) to Boston (BOS)
- Flights from Bangor (BGR) to Boston (BOS)
- Flights from Nashville (BNA) to Boston (BOS)
- Flights from Buffalo (BUF) to Boston (BOS)
- Flights from Columbus (CMH) to Boston (BOS)
- Flights from Dallas (DFW) to Boston (BOS)
- Flights from Duluth (DLH) to Boston (BOS)
- Flights from Detroit (DTW) to Boston (BOS)
- Flights from Washington (IAD) to Boston (BOS)
- Flights from New York (LGA) to Boston (BOS)
- Flights from Minneapolis (MSP) to Boston (BOS)
- Flights from Chicago (ORD) to Boston (BOS)
- Flights from Plattsburgh (PBG) to Boston (BOS)
- Flights from Ottawa (YOW) to Boston (BOS)
- Flights from Montreal (YUL) to Boston (BOS)
- Flights from Vancouver (YVR) to Boston (BOS)
- Flights from Winnipeg (YWG) to Boston (BOS)