Cheap flights To Sturbridge (CEF) from $65

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

Cheap Flights to Sturbridge from $65 One Way, $100 Round Trip

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

Wed, Jan 28 - Wed, Feb 4
LAX
Los Angeles Intl.
BOS
Logan Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jan 28 from Los Angeles Intl. to Logan Intl., returning Wed, Feb 4, priced at $100 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Jan 17 from O'Hare Intl. to Logan Intl., returning Tue, Jan 20, priced at $127 just found
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Delta flight, departing Sat, Jan 17 from O'Hare Intl. to Logan Intl., returning Tue, Jan 20, priced at $127 just found
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select American Airlines flight, departing Sat, Jan 17 from O'Hare Intl. to Logan Intl., returning Tue, Jan 20, priced at $127 just found
Thu, Jan 1 - Mon, Jan 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$132 Roundtrip, found 6 hours ago
$132
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Jan 1 from O'Hare Intl. to Logan Intl., returning Mon, Jan 5, priced at $132 found 6 hours ago
Tue, Feb 10 - Sat, Feb 21
ORD
O'Hare Intl.
BDL
Bradley Intl.
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Feb 10 from O'Hare Intl. to Bradley Intl., returning Sat, Feb 21, priced at $139 found 3 days ago
Tue, Feb 3 - Wed, Feb 4
ORD
O'Hare Intl.
BOS
Logan Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 3 from O'Hare Intl. to Logan Intl., returning Wed, Feb 4, priced at $147 found 1 day ago
Tue, Jan 20 - Sat, Jan 24
LAX
Los Angeles Intl.
BOS
Logan Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jan 20 from Los Angeles Intl. to Logan Intl., returning Sat, Jan 24, priced at $193 found 1 day ago
Wed, Jan 28 - Tue, Feb 3
SFO
San Francisco Intl.
BOS
Logan Intl.
$197 Roundtrip, found 16 hours ago
$197
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, Jan 28 from San Francisco Intl. to Logan Intl., returning Tue, Feb 3, priced at $197 found 16 hours ago
Wed, Feb 11 - Sun, Feb 22
SFO
San Francisco Intl.
BDL
Bradley Intl.
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Feb 11 from San Francisco Intl. to Bradley Intl., returning Sun, Feb 22, priced at $201 found 4 days ago

Sturbridge Flight Information

Traveling To
Sturbridge
Destination Airport IATA Code
CEF
Number of Airlines Serving
Airlines
United, Frontier Airlines, Delta, JetBlue Airways, American Airlines, Southwest Airlines, Spirit Airlines
Flight Price
$100
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Sturbridge economy flight packages

Price found within the past 48 hours. Click for updated prices.
citizenM Boston Back Bay
4.0-star property

citizenM Boston Back Bay

Jan 29 - Feb 3

5 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $614, price is now $379 per person
$379
per person
found 1 day ago
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Jan 28 - Feb 2

5 night stay

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Roundtrip • Coach
Price was $1,290, price is now $429 per person
$429
per person
found 11 hours ago
The Whitney Hotel
4.0-star property

The Whitney Hotel

Jan 29 - Feb 3

5 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,189, price is now $681 per person
$681
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Sturbridge
View all trips

Sturbridge premium economy flight packages

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

The Dagny Boston

9.4/10 Exceptional! (6,707 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $724, price is now $617 per person
$617
per person
found 2 hours ago
Design and location are top tier. Bedding was indulgent and staff were helpful and welcoming

Reviewed on Sep 8, 2025

The Bostonian Boston
4.0-star property

The Bostonian Boston

8.2/10 Very Good! (1,939 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $742, price is now $632 per person
$632
per person
found 2 hours 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

Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

8.6/10 Excellent! (1,728 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $740, price is now $631 per person
$631
per person
found 2 hours ago
Very private but convenient

Reviewed on Sep 9, 2025

Don't see what you're looking for?
See all available trips from Chicago to Sturbridge
View all trips

Sturbridge

When you plan to buy tickets for flights to Sturbridge, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Sturbridge flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Sturbridge Flights

Orbitz offers deeply discounted flights to Sturbridge, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Sturbridge? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Sturbridge flights.

Frequently asked questions

Which airlines fly to Sturbridge?
With 20 airlines providing services to Logan Intl. Airport (BOS), the gateway to Sturbridge, you have loads of choice. Score an impressive deal among these renowned international airlines that'll take you to this city:

  • JetBlue - 175 flights to Sturbridge per month
  • Delta - 158 flights to Sturbridge per month
  • Air Canada - 151 flights to Sturbridge per month

How much is a flight to Sturbridge?
Return flights to Sturbridge this week fluctuated between $100 and $201. If you were flying one-way out of Chicago (ORD), you could have landed tickets from as low as $65.
How to book the cheapest flight to Sturbridge?
Picking up cheap flights to Sturbridge is as easy as booking with Orbitz. But if you'd love to make sure you're walking away with the best flight deals around, here are some suggestions to keep in mind:

  • Depending on your departure city, choose the 'Nearby airports' function (located under the departure and arrival form fields). In some cases, alternative departure points offer more value for money.
  • If your plans aren't carved in stone, click on the 'Show flexible dates' option to compare flight deals across different departure dates. You may find an even better fare.
  • You can also select the 'Show options' link to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • Book as soon as you've sorted your travel dates. While it does happen on occasion, tickets rarely get more affordable as your date of departure nears.
  • Make serious savings on your vacation by bundling your flights, hotels and car rentals into one handy package. Your travel budget will thank you for it.
  • Don't travel during the busy season if possible. By avoiding summer, school vacations and other popular dates, you can save plenty on your airfare.

What is the best time to book a flight to Sturbridge?
Pick up a bargain and secure your seats to Sturbridge in January. If you've missed this month, fear not. February and August often have affordable airfares as well. Just be careful you don't snooze on a sale — cheap flights appear and vanish in the tap of a button!
What day of the week is the cheapest to book a flight to Sturbridge?
When it comes to cheap flights to Sturbridge, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Sturbridge?
Think about departing early in the week to score cheap flights to Sturbridge. Orbitz data from 2020 suggests Monday is normally the cheapest day to take off, followed by Tuesday. Saturday was found to have the highest airfares. This is probably because most passengers choose to begin their getaway when the working week is over.
What is the cheapest month to fly to Sturbridge?
Consider jetting off sometime in August if you're sticking to a budget. Orbitz data has found that it's generally the best month for cheap flights to Sturbridge. June is when prices hit their peak.
Which airlines allow free cancellation?
We understand that plans change and flexibility is important. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll find you fares more flexible than candy on a dashboard in summer!
What do I need for the flight to Sturbridge?
Flying can be fun if you're well prepared! Make your trip a comfortable one with the following useful tips:

  • Your travel documents are the most important things you'll need to carry on your flight to Sturbridge. To avoid any confusion at the time of check-in, make sure that the personal info on your ticket corresponds with your government-issued photo ID.
  • Take some activities to keep you entertained on your journey to Sturbridge. Magazines, books and electronic devices like tablets and e-readers are good ideas. Be sure to take a bottle of water too. Even on short flights, it's important to remain well-hydrated.
  • Even if you're flying when it's 100 degrees outside, take a sweater or hoodie on board with you. Airplane cabins can get a bit chilly!

How do I get cheap first-class/business deals to Sturbridge?
There are ways of booking business or first-class tickets to Sturbridge that won't burn a hole through your budget. Find a seat at the front of the plane for less with these great tips:

  • Being flexible doesn't just help with your yoga. Have some room to move around your travel dates so you can pick up cheaper airfares when a big sale drops.
  • Search for a budget airline that offers seats in business class. They usually come with more space and a glass of Champagne — and a more appealing price.
  • Bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat up the front. You may also be able to upgrade with points earned through a flight loyalty scheme.

What is the best time to go to Sturbridge?
There's no right or wrong time to visit Sturbridge, though May, August and September are the liveliest months. For most places in the Northern Hemisphere, summer starts June 20. If you'd sooner spend most of your days in a T-shirt than a heavy winter coat, this time of year would be perfect for you. Expect average daily highs of 80 ºF and nighttime lows around 60 ºF.
Travel tips for Sturbridge

  • Start your sightseeing in the downtown area and take a walking tour of the city's renowned attractions. Old Sturbridge Village and Brimfield Antique Show are a couple of favorites with visitors.
  • You'll find rewarding day trips a short commute from Sturbridge's hustle and bustle. Set out for Naismith Memorial Basketball Hall of Fame first and then make tracks to Volleyball Hall of Fame.
  • Get your bum in the driver's seat and discover what else makes Worcester County a magnet for adventurers. Reserve a car rental with Orbitz and enjoy the bright lights of two more must-do cities — Bolton and Athol.

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.