$54 Cheap flight deals from Orlando (ORL) to Chicopee (SFY)
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This Weekend's Flight Deals from Orlando to Chicopee
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.
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$201 Roundtrip, found 21 hours ago
$201
Roundtrip
found 21 hours ago
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$201 Roundtrip, found 21 hours ago
$201
Roundtrip
found 21 hours ago
MCO
Orlando Intl.
BDL
Bradley Intl.
$355 Roundtrip, found 3 hours ago
$355
Roundtrip
found 3 hours ago
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$380 Roundtrip, found 6 days ago
$380
Roundtrip
found 6 days ago
Airfares from $54 One Way, $102 Round Trip from Orlando to Chicopee
Prices starting at $102 for return flights and $54 for one-way flights to Chicopee were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
SFB
Orlando
PSM
Portsmouth
$102 Roundtrip, found 8 hours ago
$102
Roundtrip
found 8 hours ago
MCO
Orlando
PSM
Portsmouth
$107 Roundtrip, found 5 days ago
$107
Roundtrip
found 5 days ago
MCO
Orlando
BDL
Hartford
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours ago
MCO
Orlando
BOS
Boston
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
MCO
Orlando
BOS
Boston
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Chicopee economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Fairmont Copley Plaza, Boston
9/10 Wonderful! (1,345 reviews)
Oct 30 - Nov 1
2 night stay
Orlando (MCO) to Boston (BOS)
Delta • Coach
Boston (BOS) to Orlando (MCO)
Breeze Airways • Coach
Price was $856, price is now $644 per person
$644
per person
found 1 day ago
There was no hairdryer in the room and we called twice but no one brought in one. Parking is not easy but the bellmen were helpful. The front desk staff were nice.
Reviewed on Sep 28, 2026
5.0-star property
The Langham, Boston
9.8/10 Exceptional! (1,006 reviews)
Nov 20 - Nov 23
3 night stay
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,167, price is now $796 per person
$796
per person
found 1 day ago
The staff were incredibly welcoming. Front Desk and Concierge (special attn to David W.) went above and beyond to ensure we had the best experience throughout our entire stay. Housekeeping and the Bellman were equally attentive. The rooms were well appointed, The linens were lovely and the pillow menu added an extra touch. We used the gym and took advantage of the pool during our stay. If you are laying over from EU as we did and awake early, great way to start your day. We would definitely recommend The Langham to friends and family.
Reviewed on Sep 27, 2026
Chicopee packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Encore Boston Harbor
9.6/10 Exceptional! (4,206 reviews)
Nov 19 - Nov 23
4 night stay
Orlando (ORL) to Boston (BOS)
Allegiant Air • PremiumEconomy
Boston (BOS) to Orlando (ORL)
Frontier Airlines • PremiumEconomy
Price was $1,298, price is now $1,043 per person
$1,043
per person
found 19 hours ago
⭐️⭐️
Very disappointing experience for a 5-star hotel.
I stayed at Encore expecting a luxury experience, but unfortunately, that was not what I received. We were woken up around 6:00 AM by protesters yelling and constantly blowing horns, which completely disrupted our stay and our ability to rest.
Because of the protest, some restaurants were closed, there was no bag service/help available, and we were forced to self-park, which was extremely inconvenient—especially at a 5-star hotel where you expect a certain level of service.
I also contacted the hotel afterward and asked if something could be done, such as a discount toward a future stay. Instead, I was only offered an upgrade, which still requires me to spend more money on another room. Considering how disruptive the experience was, I don’t feel that was an appropriate resolution.
I understand that protests and outside circumstances may not always be within the hotel’s control, but the way the situation was handled and the lack of meaningful compensation were disappointing.
Encore, you need to do better. When guests pay for a 5-star experience, they should feel that their concerns are genuinely valued and addressed.
Reviewed on Sep 28, 2026
5.0-star property
Boston Harbor Hotel
9.8/10 Exceptional! (1,005 reviews)
Nov 19 - Nov 23
4 night stay
Orlando (ORL) to Boston (BOS)
Allegiant Air • PremiumEconomy
Boston (BOS) to Orlando (ORL)
Frontier Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,860, price is now $1,410 per person
$1,410
per person
found 19 hours ago
5.0-star property
The Langham, Boston
9.8/10 Exceptional! (1,006 reviews)
Nov 19 - Nov 23
4 night stay
Orlando (ORL) to Boston (BOS)
Allegiant Air • PremiumEconomy
Boston (BOS) to Orlando (ORL)
Frontier Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,667, price is now $1,293 per person
$1,293
per person
found 19 hours ago
The staff were incredibly welcoming. Front Desk and Concierge (special attn to David W.) went above and beyond to ensure we had the best experience throughout our entire stay. Housekeeping and the Bellman were equally attentive. The rooms were well appointed, The linens were lovely and the pillow menu added an extra touch. We used the gym and took advantage of the pool during our stay. If you are laying over from EU as we did and awake early, great way to start your day. We would definitely recommend The Langham to friends and family.
Reviewed on Sep 27, 2026
More About Flying To Chicopee from Orlando
Route Information for Flights from Orlando to Chicopee
Origin Airport IATA Code | ORL |
|---|---|
Destination Airport IATA Code | SFY |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Orlando to Chicopee
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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.