Cheap flights To Holyoke (SFY) from $57

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Cheap Flights to Holyoke from $57 One Way, $112 Round Trip

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

Tue, Jan 20 - Tue, Jan 20
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$112 Roundtrip, found 14 hours ago
$112
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Jan 20 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jan 20, priced at $112 found 14 hours ago
Fri, Dec 5 - Fri, Dec 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$113 Roundtrip, found 5 hours ago
$113
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Fri, Dec 5 from O'Hare Intl. to Logan Intl., returning Fri, Dec 5, priced at $113 found 5 hours ago
Tue, Dec 9 - Wed, Dec 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$114 Roundtrip, found 6 hours ago
$114
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Dec 9 from O'Hare Intl. to Logan Intl., returning Wed, Dec 10, priced at $114 found 6 hours ago
Mon, Dec 8 - Wed, Dec 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$116 Roundtrip, found 2 hours ago
$116
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Dec 8 from O'Hare Intl. to Logan Intl., returning Wed, Dec 10, priced at $116 found 2 hours ago
Thu, Dec 4 - Wed, Dec 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Dec 4 from O'Hare Intl. to Logan Intl., returning Wed, Dec 10, priced at $117 found 1 hour ago
Sat, Feb 14 - Tue, Feb 17
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Feb 14 from Ronald Reagan Washington National to Logan Intl., returning Tue, Feb 17, priced at $117 found 5 days ago
Sat, Feb 14 - Tue, Feb 17
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Feb 14 from Ronald Reagan Washington National to Logan Intl., returning Tue, Feb 17, priced at $117 found 5 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Jan 17 from O'Hare Intl. to Logan Intl., returning Tue, Jan 20, priced at $117 found 4 hours ago
Wed, Dec 31 - Thu, Jan 1
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$119 Roundtrip, found 6 hours ago
$119
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Dec 31 from Ronald Reagan Washington National to Logan Intl., returning Thu, Jan 1, priced at $119 found 6 hours ago
Mon, Dec 8 - Wed, Dec 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$119 Roundtrip, found 2 hours ago
$119
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Dec 8 from O'Hare Intl. to Logan Intl., returning Wed, Dec 10, priced at $119 found 2 hours ago

Holyoke Flight Information

Traveling To
Holyoke
Destination Airport IATA Code
SFY
Number of Airlines Serving
Airlines
Spirit Airlines, JetBlue Airways, Delta, American Airlines, Frontier Airlines, United
Flight Price
$112
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Holyoke economy flight packages

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

The Revolution Hotel

Dec 17 - Dec 20

3 night stay

Atlanta (ATL) to Boston (BOS)

United • Non-stop • Coach

Boston (BOS) to Atlanta (ATL)

JetBlue Airways • Non-stop • Coach
Price was $428, price is now $290 per person
$290
per person
found 1 day ago
Cambria Hotel Boston Somerville
3.0-star property

Cambria Hotel Boston Somerville

Dec 10 - Dec 15

5 night stay

Atlanta (ATL) to Boston (BOS)

United • Non-stop • Coach

Boston (BOS) to Atlanta (ATL)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $597, price is now $372 per person
$372
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Dec 17 - Dec 20

3 night stay

Atlanta (ATL) to Boston (BOS)

United • Non-stop • Coach

Boston (BOS) to Atlanta (ATL)

JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,360, price is now $869 per person
$869
per person
found 1 day ago
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Holyoke premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport
3.5-star property

Embassy Suites Boston Logan Airport

8.8/10 Excellent! (2,117 reviews)

Dec 26 - Jan 3

8 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,355, price is now $949 per person
$949
per person
found 1 day ago
We had an excellent stay! Everything was clean and breakfast was convenient and tasty! The only thing that could make it better would be parking options other than the $60/day valet.

Reviewed on Aug 6, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (475 reviews)

Dec 26 - Jan 3

8 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,519, price is now $1,840 per person
$1,840
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

The Revolution Hotel
3.5-star property

The Revolution Hotel

9/10 Wonderful! (2,173 reviews)

Dec 26 - Jan 3

8 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,224, price is now $977 per person
$977
per person
found 1 day ago
Very clean, staff friendly, amazing location

Reviewed on Oct 30, 2025

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See all available trips from Chicago to Holyoke
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Holyoke first class flight packages

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

The Whitney Hotel

9.6/10 Exceptional! (475 reviews)

Dec 12 - Dec 15

3 night stay

San Juan (SJU) to Boston (BOS)

United • Non-stop • FirstClass

Boston (BOS) to San Juan (SJU)

American Airlines • Non-stop • FirstClass
Price was $1,542, price is now $1,298 per person
$1,298
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

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,019 reviews)

Dec 12 - Dec 15

3 night stay

San Juan (SJU) to Boston (BOS)

United • Non-stop roundtrip • FirstClass
Price was $2,098, price is now $1,681 per person
$1,681
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (169 reviews)

Dec 12 - Dec 15

3 night stay

San Juan (SJU) to Boston (BOS)

United • Non-stop roundtrip • FirstClass
Price was $2,080, price is now $1,718 per person
$1,718
per person
found 1 day ago
Excellent services.

Reviewed on Dec 29, 2024

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Holyoke

Traveling to Holyoke and need a cheap flight? Orbitz has great deals on flights to Holyoke right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Holyoke Quickly and Hassle-Free

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Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Holyoke or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Holyoke flights. When you need us, we’re here for you!

Frequently asked questions

Which airlines fly to Holyoke?
Book a ticket with one of the 20 airlines that fly in and out of Bradley Intl. Airport (BDL) and this glorious city will be yours to explore. Whenever you're looking to head off, you're bound to find a flight that matches your schedule. Check out these leading international carriers that'll get you to Holyoke:

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

What is the best airport to fly to in Holyoke?
Find yourself a rewarding flight deal to Bradley Intl. Airport (BDL). It's the main airport servicing this city and is situated around 20 miles south of the downtown area. Once you've walked out of arrivals, it won't be long before you're exploring the delights of Holyoke.
How much is a flight to Holyoke?
Fares for round-trip flights dropped as low as $112 this week to Holyoke, and rose as high as $119. Several lucky travelers flying out of Chicago (ORD) managed to snare one-way flights starting from just $57.
How to book the cheapest flight to Holyoke?
Picking up cheap flights to Holyoke is as easy as booking your ticket with Orbitz. But if you want to make sure you're walking away with the best flight deals around, here are a few tips worth following:

  • Consider departing from or arriving at alternative airports to save on your airfare. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list any available options.
  • Also, click on the 'Show flexible dates' link and you'll see the prices for days around your chosen departure. It's possible to score cheaper flight deals if your dates are flexible.
  • You can also hit the 'Show options' function to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd like to fly.
  • Once you've sorted out your travel dates, don't waste time booking your flight. Prices normally get more expensive as the departure date nears.
  • Make greater savings on your trip by bundling your flights, hotels and car rental into an Orbitz package deal. Your credit card will thank you.
  • If practical, avoid traveling in high seasons. Airfares surge during school breaks, summer and other vacation periods like Thanksgiving and Christmas.

How long is a flight to Holyoke?
Your point of origin, which airport you fly out of and whether you have a layover — flight times depend on lots of factors. But we've made life simple and compiled the average times for some of the most common routes to Holyoke:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 10 minutes
  • Orlando, FL (MCO-Orlando Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 39 minutes
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) to Bradley Intl. Airport (BDL) - 1 hour and 25 minutes

What is the best time to book a flight to Holyoke?
On average, the cheapest month to purchase a plane ticket is January. This is followed by February then August. When looking for a cheap flight to Holyoke, it's always good to be ready to book. Cheap deals emerge in an instant and don't wait around!
What day of the week is the cheapest to book a flight to Holyoke?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days to purchase seats to Holyoke. The vacation of your dreams starts with a terrific flight deal!
What is the cheapest day of the week to fly to Holyoke?
If you're looking for cheap flights to Holyoke, leave earlier in the week. Orbitz data from 2020 shows Monday is the most affordable day to set off, followed by Tuesday. Saturday has the most expensive fares, so avoid this day and do your budget a favor.
What is the cheapest month to fly to Holyoke?
Based on Orbitz data, you'll want to fly out in August. This is generally a great month to land cheap flights to Holyoke. Be aware that the most expensive time to get on a plane is in June.
Which airlines allow free cancellation?
If you're concerned your travel plans could change, Orbitz can help you lock in a flexible ticket. All you need to do is click on "Filter by flexible change policies" when searching for your Holyoke flights. We'll show you airlines that include free cancellation within 24 hours and no change fees — along with our famous low prices.
What do I need for the flight to Holyoke?
The secret to a successful flight is preparation. Here are some useful tips to help you get ready for departure:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any problems during check-in, make sure that the personal info on your ticket matches your government-issued photo ID.
  • Make time fly by even faster on your short flight by packing the right things. Think a water bottle, snacks and entertainment. If you want your trip to Holyoke to pass quietly, toss some headphones or earplugs in your carry-on bag as well.
  • It can get cold on the plane. If you'd prefer not to shiver your way through the flight, wear another layer of clothing.

How many direct flights are there to Holyoke?
There are 175 direct flights every month to Holyoke. When it comes to airlines that will fly you there, you've got loads of choice. American Airlines, Delta Air Lines and Southwest Airlines are among the most popular. United Airlines, JetBlue Airways and Spirit Airlines are some other reputable carriers offering nonstop services.
How do I get cheap first-class/business deals to Holyoke?
If you think a first or business-class fare is out of your price range, you may want to think again. Here are a few practical tips to help you nab a premium flight to Holyoke for less:

  • Flexibility is everything. By being open to different travel dates, you'll have a better chance of picking up a deal on first or business-class airfares.
  • A lot of low-cost carriers have excellent business-class seating without the hefty fees.
  • Bid for an upgrade in online auctions (if available) or upgrade your ticket with frequent flyer loyalty programs.

How to get into Holyoke from the airport?
Driving is a great option. Payless, Budget and Alamo are three car rental agencies located at Bradley Intl. Airport (BDL). After picking up a Bradley Intl. Airport (BDL) car rental, you can head directly from BDL airport to downtown Holyoke, approximately 20 miles to the north. Or, if you'd prefer to rent a ride from the city center, have a look through our Holyoke car rentals.
What is the best time to go to Holyoke?
Travelers come from every direction to go to Holyoke in February, March and April. So if you want to discover this fabulous destination in the tourist season, this is the best time to go. Like most places in the Northern Hemisphere, the summer starts June 20 in Holyoke, with average daily temperatures fluctuating between 55 ºF and 80 ºF.

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.