
$72 Cheap flight deals from Chicago (CHI) to Greenfield (CEF)
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 Greenfield
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 $72 One Way, $135 Round Trip from Chicago to Greenfield
Prices starting at $135 for return flights and $72 for one-way flights to Greenfield were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Greenfield economy flight packages

The Langham, Boston
Apr 30 - May 3
Chicago (CHI) to Boston (BOS)
Reviewed on Jan 12, 2026

Boston Harbor Hotel
Apr 30 - May 3
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 24, 2024

Raffles Boston
Apr 30 - May 3
Chicago (CHI) to Boston (BOS)
Reviewed on Dec 29, 2024
Greenfield packages with premium economy flights

The Revolution Hotel
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on Jan 19, 2026

Boston Harbor Hotel
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 24, 2024

Eurostars The Boxer
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on May 6, 2025
Greenfield first class flight packages

Arcadian Hotel
May 22 - May 24
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 20, 2026

Eurostars The Boxer
May 22 - May 24
Chicago (CHI) to Boston (BOS)
Reviewed on May 6, 2025
More About Flying To Greenfield from Chicago
Route Information for Flights from Chicago to Greenfield
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | CEF |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Greenfield
If you are looking online for bargain Chicago to Greenfield flights, Orbitz is your ideal destination. We understand that vacations can be expensive and offer guaranteed low prices on our domestic and international tickets.
Orbitz Uses Cutting-Edge Mobile Tools
Orbitz may offer low cost Chicago to Greenfield flights but this does not mean that we skimp on giving you the latest mobile apps. You don’t have to worry about checking your flight status as we send the info for your flights from Chicago to Greenfield directly to your smartphone.
Fly Cheap and Earn Miles on Your Chicago to Greenfield Flights
Frequent flyer miles and points are great—and even better when you earn them on cheap flights from Chicago to Greenfield. With Orbitz, you can earn miles for your frequent flyer program on qualified flights. Enter your frequent flyer number when you book with us to get rewarded for your flight.
Orbitz Takes the Hassle Out Of Flying
We know that flying can be stressful, particularly if you are traveling with young children. That’s why we make sure you are aware of any changes or delays to your flights from Chicago to Greenfield via your phone or email address. We can even inform family members too.
Orbitz Flights Fit Around Your Lifestyle
Orbitz understands that you don’t necessarily want to fly at 5:00 a.m—and that sometimes you do. This is why we allow you to find the best Chicago to Greenfield flights at the times you want with ease.
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 London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
More Destinations
- Flights from Atlanta to The Berkshires
- Flights from Austin to The Berkshires
- Flights from Charlotte to The Berkshires
- Flights from Chicago to The Berkshires
- Flights from Cleveland to The Berkshires
- Flights from Columbus to The Berkshires
- Flights from Dallas to The Berkshires
- Flights from Denver to The Berkshires
- Flights from Houston to The Berkshires
- Flights from Indianapolis to The Berkshires
- Flights from Las Vegas to The Berkshires
- Flights from Los Angeles to The Berkshires
- Flights from Minneapolis - St. Paul to The Berkshires
- Flights from Nashville to The Berkshires
- Flights from New Orleans to The Berkshires
- Flights from Philadelphia to The Berkshires
- Flights from Phoenix to The Berkshires
- Flights from Portland to The Berkshires
- Flights from St. Louis to The Berkshires
- Flights from Washington to The Berkshires
- Flights from Myrtle Beach to The Berkshires
- Flights from Pittsburgh to The Berkshires
- Flights from Fort Lauderdale to The Berkshires
- Flights from Milwaukee to The Berkshires
- Flights from Rochester to The Berkshires
- Flights from Tucson to The Berkshires
- Flights from Tampa to The Berkshires
- Flights from Jacksonville to The Berkshires
- Flights from Louisville to The Berkshires
- Flights from State College to The Berkshires
- Flights from Chattanooga to The Berkshires
- Flights from Detroit to Pittsfield
- Flights from Orlando to Pittsfield
- Flights from Salt Lake City to Pittsfield
- Flights from Vancouver to Pittsfield
- Flights from Charleston to Pittsfield
- Flights from Mukah to Pittsfield
- Flights from Moline to Pittsfield
- Flights from Monroe to Pittsfield
- Flights from Syracuse to Pittsfield
- Flights from Santa Barbara to Pittsfield
- Flights from Madison to Pittsfield
- Flights from Louisville to Pittsfield
- Flights from Baton Rouge to Pittsfield
- Flights from Augusta to Pittsfield
- Flights from Fayetteville to Pittsfield
- Flights from Chattanooga to Pittsfield
- Flights from Columbus to Shelburne Falls
- Flights from Toledo to Shelburne Falls
- Flights from Bloomington to Shelburne Falls
- Flights from Fairbanks to Lenox
- Flights from Chicago to Lenox
- Flights from Dublin to Lenox
- Flights from Los Angeles to Lenox
- Flights from Minneapolis - St. Paul to Lenox
- Flights from Phoenix to Lenox
- Flights from Raleigh to Lenox
- Flights from San Antonio to Lenox
- Flights from Washington to Lenox
- Flights from Frankfurt to Lenox
- Flights from Tokyo to Lenox
- Flights from Roanoke to Lenox
- Flights from Sarasota to Lenox
- Flights from Fort Myers to Lenox
- Flights from Harrisburg - Hershey to Lenox
- Flights from Oklahoma City to Lenox
- Flights from Bangor to Lenox
- Flights from Tri-Cities to Lenox
- Flights from New York to Deerfield
- Flights from Providence to Deerfield
- Flights from Syracuse to Deerfield
- Flights from Milwaukee to Deerfield
- Flights from Tampa to Deerfield
- Flights from Savannah to Deerfield
- Flights from Atlanta to Hadley
- Flights from Baltimore to Hadley
- Flights from Bloomington to Hadley
- Flights from Rochester to Hadley
- Flights from White Plains to Hadley
- Flights from Covington to Hadley
- Flights from Chattanooga to Hadley
- Flights from Salt Lake City to Williamstown
- Flights from Hamburg to Williamstown
- Flights from Sarasota to Williamstown
- Flights from Oklahoma City to Williamstown
- Flights from Grand Rapids to Williamstown
- Flights from Flint to Amherst
- Flights from Atlanta to Amherst
- Flights from Charlotte to Amherst
- Flights from Detroit to Amherst
- Flights from Providence to Amherst
- Flights from Portland to Amherst
- Flights from Pittsburgh to Amherst
- Flights from Richmond to Amherst
- Flights from Syracuse to Amherst
- Flights from Madison to Amherst
- Flights from Norfolk - Virginia Beach to Amherst
- Flights from Dayton to Amherst
- Flights from Jacksonville to Amherst
- Flights from Covington to Amherst
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.




