Cheap flights To Greenfield (CEF) from $44

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Cheap Flights to Greenfield from $44 One Way, $100 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 4 - Fri, Dec 11
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Bradley Intl., returning Fri, Dec 11, priced at $100 found 3 days ago
Fri, Dec 4 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $102 found 3 days ago
Sat, Nov 14 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Sat, Nov 14 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 14, priced at $104 found 2 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $118 just found
Sat, Oct 24 - Sun, Oct 25
MCO
Orlando Intl.
BOS
Logan Intl.
$142 Roundtrip, found 4 hours ago
$142
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Sun, Oct 25, priced at $142 found 4 hours ago
Mon, Apr 19 - Wed, Apr 28
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$150 Roundtrip, found 10 hours ago
$150
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Mon, Apr 19 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Wed, Apr 28, priced at $150 found 10 hours ago
Sat, Oct 24 - Tue, Oct 27
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Oct 24 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Oct 27, priced at $159 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
BOS
Logan Intl.
$162 Roundtrip, found 22 hours ago
$162
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Sat, Oct 31, priced at $162 found 22 hours ago
Wed, Oct 28 - Tue, Nov 3
MCO
Orlando Intl.
BOS
Logan Intl.
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 28 from Orlando Intl. to Logan Intl., returning Tue, Nov 3, priced at $162 found 1 day ago
Tue, Nov 3 - Sat, Nov 7
TPA
Tampa Intl.
BDL
Bradley Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Nov 3 from Tampa Intl. to Bradley Intl., returning Sat, Nov 7, priced at $165 found 1 day ago

Greenfield Flight Information

Traveling To
Greenfield
Destination Airport IATA Code
CEF
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways, Frontier Airlines, Southwest Airlines, JetBlue Airways, Delta, American Airlines
Flight Price
$100
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Greenfield economy flight packages

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

Nov 1 - Nov 3

2 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $641, price is now $389 per person
$389
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 1 - Nov 3

2 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,040, price is now $652 per person
$652
per person
found 1 day ago
Mandarin Oriental, Boston
5.0-star property

Mandarin Oriental, Boston

Nov 9 - Nov 12

3 night stay

Orlando (MCO) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,007, price is now $1,345 per person
$1,345
per person
found 20 hours ago
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Greenfield premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
3.5-star property

Arcadian Hotel

8.2/10 Very Good! (4,438 reviews)

Nov 3 - Nov 8

5 night stay

Detroit (DTW) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,398, price is now $1,094 per person
$1,094
per person
found 1 day ago

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (312 reviews)

Nov 3 - Nov 8

5 night stay

Detroit (DTW) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $2,529, price is now $1,971 per person
$1,971
per person
found 1 day ago

Good Hotels Boston
2.0-star property

Good Hotels Boston

8/10 Very Good! (57 reviews)

Nov 3 - Nov 8

5 night stay

Detroit (DTW) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,517, price is now $1,259 per person
$1,259
per person
found 1 day ago
Quant, convenient, historic, well priced. Difficult stairs, no elevators.

Reviewed on Aug 24, 2026

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Greenfield first class flight packages

Price found within the past 48 hours. Click for updated prices.
Bricco Suites
3.5-star property

Bricco Suites

9/10 Wonderful! (999 reviews)

Oct 31 - Nov 4

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,067, price is now $869 per person
$869
per person
found 1 day ago
What a great place to stay. Right in the heart of everything fun and great in Boston. Small, quaint and friendly. We had a great time.

Reviewed on Sep 16, 2026

The Monty Boston
2.5-star property

The Monty Boston

9.6/10 Exceptional! (40 reviews)

Oct 31 - Nov 4

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,762, price is now $2,214 per person
$2,214
per person
found 1 day ago
Amazing place for a group. It was super clean and a great location in Boston. It’s a city with homeless population so the only negative was the entrance way to the building smelled like pee. Nothing the building can do, but just something to know. I will defiantly stay there next time.

Reviewed on Jul 3, 2026

Omni Parker House
4.5-star property

Omni Parker House

9/10 Wonderful! (3,703 reviews)

Oct 31 - Nov 4

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,293, price is now $1,066 per person
$1,066
per person
found 1 day ago
Great central location to tourist sites. Beautiful hotel lobby and common spaces. Very nice staff at front desk and restaurants.

Reviewed on Sep 18, 2026

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Greenfield

If you are looking for affordable flights to Greenfield, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Greenfield now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Greenfield flights. With Orbitz, booking flights to Greenfield is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Greenfield flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Greenfield flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Greenfield flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

Which airlines fly to Greenfield?
Book a ticket with one of the 20 airlines that travel to Bradley Intl. Airport (BDL) and this fantastic city will be yours to explore. Whenever you're planning to get away, you're certain to find a flight that matches your schedule. Take a look at these popular international carriers that touch down in Greenfield:

  • Air Canada - 17 flights to Greenfield per month
  • JetBlue - 16 flights to Greenfield per month

How much is a flight to Greenfield?
If you're looking for a return flight, airfares ranged from $100 to $165 this week. The best price to travel one-way was $44, from Fort Lauderdale (FLL).
How to book the cheapest flight to Greenfield?
Picking up cheap flights to Greenfield is as easy as booking your ticket with Orbitz. But if you'd love to make sure you're nabbing the best flight deals around, here are some suggestions worth following:

  • Departing from or arriving at other airports may be more affordable. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below the form fields to explore your options.
  • Similarly, click on the 'Show flexible dates' option and you'll see the prices for days around your chosen departure. It's possible to pick up cheaper flight deals if your travel plans are flexible.
  • Hit 'Show options' to filter your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • Reserve your fare as soon as you've decided on your travel dates. While you can get lucky now and then, tickets rarely get cheaper as your date of departure approaches.
  • Save on your trip by bundling your hotel, flights and car rentals into an Orbitz package deal. Your travel budget will thank you for it.
  • If possible, don't fly in peak seasons. Airfares significantly increase during summer, school breaks and around other vacation times like Easter and Thanksgiving.

What is the best time to book a flight to Greenfield?
If you can, book your flights to Greenfield in January. This is the best month for low airfares, closely followed by February and August. With a bit of organizing, you're guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Greenfield?
If you're after cheap fares to Greenfield, the best days of the week to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to Greenfield?
Consider departing early in the week to nab cheap flights to Greenfield. Orbitz data from 2020 indicates Monday is normally the most inexpensive day to fly out, followed by Tuesday. Saturdays were shown to have the most expensive ticket prices. This is probably because many passengers prefer to kick off their vacation at the end of the week.
What is the cheapest month to fly to Greenfield?
We won't keep you guessing — based on Orbitz data, August is generally the most inexpensive month to fly. Perfect for those who need a weekend getaway or just an escape from it all before the weather turns. Be aware that the least affordable time to fly is the height of summer, with airfares peaking in June.
Which airlines allow free cancellation?
Flexibility is important, that's why Orbitz lets you search for flights that won't hit you with a fee for amending your reservation. Fill out your departure and arrival points, then select "Filter by flexible change policies." We'll show you options that include free cancellation and no change fees.
What do I need for the flight to Greenfield?
Flying doesn't have to be a drag. In fact it can be fun with a bit of pre-planning! Make your journey a total breeze with these useful tips:

  • Before you step on to the plane, you'll need to present some form of government-issued ID, such as your passport. You'll also need your boarding pass. If you're traveling with children, check with your airline about which documents they may need.
  • To keep you busy on the short hop to Greenfield, download some new songs or restock the podcast library on your tablet. Food can also be a tasty distraction while in the air, so take some snacks.
  • It can get cold on the plane. If you don't like the thought of shivering your way through the flight, dress in layers.

How do I get cheap first-class/business deals to Greenfield?
There are ways of booking business or first-class tickets to Greenfield that won't burn through your wallet. Snap up a seat in the pointy end of the plane for less with these handy hints:

  • Flexibility is everything. By being open to different travel dates, you'll have better odds of spotting a sale on your airfares.
  • Many budget carriers these days offer terrific business or premium-class seating that doesn't cost the earth.
  • Make the most of your airline's customer loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to Greenfield?
Anytime is a fantastic time to experience Greenfield, but February, July and August are the liveliest months. Like most places in the Northern Hemisphere, summertime begins June 20. If you'd rather hang out in a lightweight top than a heavy winter jacket, this time of the year would be ideal. Expect average daytime highs of 80 ºF and nightly lows around 55 ºF.
Travel tips for Greenfield

  • Begin in the downtown area and enjoy a walking tour of a few of the city's fantastic attractions. Greenfield Community College and Poet's Seat Tower are traveler favorites.
  • You'll also want to check out the sights a short drive from Greenfield's center. Meander around Naismith Memorial Basketball Hall of Fame and Volleyball Hall of Fame and experience another side of this vibrant destination.
  • When the time comes to discover more of Massachusetts, book a car rental and hit the road for Boston. Springfield is another interesting city with ample things to do and see.

More to Explore

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.