$109 Cheap flight deals from Chicago (CHI) to Dedham (BOS)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Chicago to Dedham
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 Dedham
Prices starting at $198 for return flights and $109 for one-way flights to Dedham were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Dedham economy flight packages
Boston Harbor Hotel
Oct 1 - Oct 4
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 25, 2026
Luxury Apartments by Hyatus at Boston Everett
Oct 1 - Oct 3
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Dedham packages with premium economy flights
The Cove at Rockport Hotel
Oct 9 - Oct 15
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 25, 2026
Boston Harbor Hotel
Oct 9 - Oct 15
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 25, 2026
More About Flying To Dedham from Chicago
Route Information for Flights from Chicago to Dedham
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Dedham
It has never been easier to find cheap Chicago to Dedham 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 Dedham 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 Dedham. 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 Dedham Flights
Finding great deals on flights from Chicago to Dedham 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 Dedham vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Dedham 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 Dedham. We send you free email and mobile alerts to keep you informed about delays to Chicago to Dedham flights.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Washington
- Chicago to London
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Sacramento
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Atlantic City
- Chicago to Hartford
More Destinations
- Flights from Austin to Brookline
- Flights from Chicago to Brookline
- Flights from Copenhagen to Brookline
- Flights from Miami to Brookline
- Flights from Minneapolis - St. Paul to Brookline
- Flights from New York to Brookline
- Flights from Philadelphia to Brookline
- Flights from Providence to Brookline
- Flights from Newark to Brookline
- Flights from Milwaukee to Brookline
- Flights from Tampa to Brookline
- Flights from Denver to Newton
- Flights from Indianapolis to Newton
- Flights from Miami to Newton
- Flights from Minneapolis - St. Paul to Newton
- Flights from New Orleans to Newton
- Flights from Washington to Newton
- Flights from Omaha to Newton
- Flights from Des Moines to Newton
- Flights from Fort Lauderdale to Newton
- Flights from Honolulu to Boston
- Flights from Wilmington to Boston
- Flights from Islip to Boston
- Flights from Amsterdam to Boston
- Flights from Atlanta to Boston
- Flights from Charlotte to Boston
- Flights from Chicago to Boston
- Flights from Cincinnati to Boston
- Flights from Dallas to Boston
- Flights from Denver to Boston
- Flights from Indianapolis to Boston
- Flights from Kansas City to Boston
- Flights from Lisbon District to Boston
- Flights from London to Boston
- Flights from Los Angeles to Boston
- Flights from Memphis to Boston
- Flights from Montreal to Boston
- Flights from New Orleans to Boston
- Flights from New York to Boston
- Flights from Orlando to Boston
- Flights from Salt Lake City to Boston
- Flights from San Antonio to Boston
- Flights from San Francisco to Boston
- Flights from St. Louis to Boston
- Flights from Vancouver to Boston
- Flights from Washington to Boston
- Flights from Paris to Boston
- Flights from Rome to Boston
- Flights from Barcelona to Boston
- Flights from Charleston to Boston
- Flights from Sacramento to Boston
- Flights from Omaha to Boston
- Flights from San Juan to Boston
- Flights from Myrtle Beach to Boston
- Flights from Des Moines to Boston
- Flights from Richmond to Boston
- Flights from Burlington to Boston
- Flights from Syracuse to Boston
- Flights from Silicon Valley to Boston
- Flights from Milwaukee to Boston
- Flights from Reno to Boston
- Flights from Madison to Boston
- Flights from Sarasota to Boston
- Flights from Niagara Falls to Boston
- Flights from Fort Myers to Boston
- Flights from Norfolk - Virginia Beach to Boston
- Flights from Rochester to Boston
- Flights from Oklahoma City to Boston
- Flights from Allentown to Boston
- Flights from Knoxville to Boston
- Flights from Birmingham to Boston
- Flights from Tampa to Boston
- Flights from Jacksonville to Boston
- Flights from Boise to Boston
- Flights from Louisville to Boston
- Flights from Grand Rapids to Boston
- Flights from Savannah to Boston
- Flights from Asheville to Boston
- Flights from Greenville - Spartanburg to Boston
- Flights from Bangor to Boston
- Flights from Palm Beach to Boston
- Flights from Atlanta to Norwood
- Flights from Charlotte to Norwood
- Flights from Chicago to Norwood
- Flights from Cleveland to Norwood
- Flights from Denver to Norwood
- Flights from Detroit to Norwood
- Flights from Houston to Norwood
- Flights from Los Angeles to Norwood
- Flights from Miami to Norwood
- Flights from New York to Norwood
- Flights from Philadelphia to Norwood
- Flights from Raleigh to Norwood
- Flights from Seattle to Norwood
- Flights from Charleston to Norwood
- Flights from Gander to Norwood
- Flights from Fort Lauderdale to Norwood
- Flights from Newark to Norwood
- Flights from Sarasota to Norwood
- Flights from Tampa to Norwood
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.