$25 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.

Sat, Nov 22 - Sat, Nov 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 5 hours ago
$114
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Nov 22 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 22, priced at $114 found 5 hours ago
Sat, Nov 22 - Sat, Nov 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 5 hours ago
$114
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Nov 22 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 22, priced at $114 found 5 hours ago
Sat, Nov 22 - Mon, Nov 24
MCO
Orlando Intl.
BDL
Bradley Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Nov 22 from Orlando Intl. to Bradley Intl., returning Mon, Nov 24, priced at $177 found 2 hours ago

Airfares from $25 One Way, $49 Round Trip from Orlando to Chicopee

Prices starting at $49 for return flights and $25 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.

Wed, Dec 10 - Sat, Dec 13
MCO
Orlando
BOS
Boston
$49 Roundtrip, found 4 hours ago
$49
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Dec 10 from Orlando to Boston, returning Sat, Dec 13, priced at $49 found 4 hours ago
Sat, Dec 13 - Sun, Dec 14
MCO
Orlando
PSM
Portsmouth
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Dec 13 from Orlando to Portsmouth, returning Sun, Dec 14, priced at $88 just found
Fri, Dec 5 - Mon, Dec 8
MCO
Orlando
BDL
Hartford
$143 Roundtrip, just found
$143
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Dec 5 from Orlando to Hartford, returning Mon, Dec 8, priced at $143 just found
Fri, Dec 5 - Sun, Dec 7
MCO
Orlando
BDL
Hartford
$167 Roundtrip, just found
$167
Roundtrip
just found
Select American Airlines flight, departing Fri, Dec 5 from Orlando to Hartford, returning Sun, Dec 7, priced at $167 just found
Wed, Dec 24 - Tue, Jan 13
MCO
Orlando
BOS
Boston
$478 Roundtrip, found 2 days ago
$478
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Dec 24 from Orlando to Boston, returning Tue, Jan 13, priced at $478 found 2 days ago

Chicopee economy flight packages

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

The Revolution Hotel

18/10 Exceptional! (2,226 reviews)

Dec 18 - Dec 22

4 night stay

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Price was $487, price is now $326 per person
$326
per person
found 1 day ago
Excellent location and a fun spot

Reviewed on Nov 14, 2025

The Bostonian Boston
4.0-star property

The Bostonian Boston

16.4/10 Exceptional! (1,946 reviews)

Dec 18 - Dec 22

4 night stay

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $590, price is now $405 per person
$405
per person
found 1 day ago
Nice hotel, great location, friendly staff. The only thing - I expected a complimentary shuttle to airport (was mentioned on Orbitz) - no. Noon checkout time is good.

Reviewed on Oct 19, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (475 reviews)

Jan 8 - Jan 12

4 night stay

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach
Price was $1,011, price is now $695 per person
$695
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

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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.