Cheap flights To Lexington (BOS) from $47

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 Lexington from $47 One Way, $84 Round Trip

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

Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$84 Roundtrip, found 5 days ago
$84
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $84 found 5 days ago
Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$92 Roundtrip, found 2 days ago
$92
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $92 found 2 days ago
Thu, Jan 21 - Thu, Jan 28
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 6 days ago
$102
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 28, priced at $102 found 6 days ago
Sun, Jan 10 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 7 hours ago
$110
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $110 found 7 hours ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $117 found 3 days ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $122 found 3 days ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$125 Roundtrip, found 7 hours ago
$125
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $125 found 7 hours ago
Sun, Jan 10 - Thu, Jan 14
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$126 Roundtrip, found 3 days ago
$126
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 14, priced at $126 found 3 days ago
Sat, Sep 19 - Sat, Oct 10
MCO
Orlando Intl.
BOS
Logan Intl.
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Sep 19 from Orlando Intl. to Logan Intl., returning Sat, Oct 10, priced at $127 found 5 days ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$130 Roundtrip, found 7 hours ago
$130
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $130 found 7 hours ago

Lexington Flight Information

Traveling To
Lexington
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways, Frontier Airlines
Flight Price
$84
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Lexington economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

Sep 29 - Oct 2

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was $701, price is now $501 per person
$501
per person
found 1 day ago
The Mansion at Ocean Edge
4.0-star property

The Mansion at Ocean Edge

Sep 29 - Oct 2

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,816, price is now $1,335 per person
$1,335
per person
found 1 day ago
Nantucket Inn
3.5-star property

Nantucket Inn

Sep 21 - Sep 26

5 night stay

Los Angeles (LAX) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,817, price is now $1,179 per person
$1,179
per person
found 19 hours ago
Don't see what you're looking for?
See all available trips from Chicago to Lexington
View all trips

Lexington premium economy flight packages

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

Arcadian Hotel

8/10 Very Good! (4,364 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,292, price is now $1,058 per person
$1,058
per person
found 1 day ago

The Charles Hotel
5.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,006 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,415, price is now $1,091 per person
$1,091
per person
found 1 day ago
Favorite hotel and brunch in Cambridge

Reviewed on Aug 7, 2026

Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

8.8/10 Excellent! (1,940 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,803, price is now $1,453 per person
$1,453
per person
found 1 day ago
No refrigerator in room? Only available upon request…strange.

Reviewed on Aug 7, 2026

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

Lexington first class flight packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

9.4/10 Exceptional! (203 reviews)

Oct 3 - Oct 7

4 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,191, price is now $992 per person
$992
per person
found 10 hours ago
Great beachfront location! Breakfast was excellent as well.

Reviewed on Aug 7, 2026

The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

9.2/10 Wonderful! (268 reviews)

Oct 3 - Oct 7

4 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,467, price is now $1,112 per person
$1,112
per person
found 10 hours ago
P Indoor pool and hot tub loved and the outdoor Shack was great

Reviewed on Jun 8, 2026

Chatham Tides
2.5-star property

Chatham Tides

9.4/10 Exceptional! (735 reviews)

Oct 3 - Oct 7

4 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,543, price is now $1,288 per person
$1,288
per person
found 10 hours ago
amazing hotel and staff were extremely helpful, location was perfect with beach access

Reviewed on Aug 7, 2026

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

Lexington

Reach your destination without breaking your budget by booking your flights to Lexington using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Lexington Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Lexington flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Lexington. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Lexington, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Lexington flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

.

Frequently asked questions

Which airlines fly to Lexington?
With 20 airlines to decide from, finding a suitable flight that matches your travel plans and budget should be a piece of cake. Logan Intl. Airport (BOS) is a major entry point to Lexington and where you'll likely be flying into. These leading international airlines are ready to take you there:

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

What is the best airport to fly to in Lexington?
Logan Intl. Airport (BOS) is the city's major airport, so your trickiest decision will be the window seat or the aisle seat. Central Lexington is roughly 12 miles away and where many travelers base themselves.
How much is a flight to Lexington?
Plenty of huge deals were there for the taking this week, with return flights to Lexington fluctuating from $84 to $130. But it was passengers departing from Orlando (SFB) who nabbed the biggest bargains. One-way tickets to Lexington started at just $47.
How to book the cheapest flight to Lexington?
With Orbitz, you'll uncover some of the most impressive flight deals around from a huge range of airlines. But if you want to increase your likelihood of booking cheap flights to Lexington, here are some tips to get started:

  • Consider departing from or arriving at alternative airports to save money. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will show you any available options.
  • Similarly, click on the 'Show flexible dates' link to view the airfares on days around your selected departure. It's possible to find cheaper flight deals if your dates are flexible.
  • To fine tune your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also select whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the most rewarding savings, so book as soon as you know your travel dates. The most affordable airfares sell out first and prices normally rise as the departure date nears.
  • Make big savings on your adventure by bundling your hotel, flights and car rentals into a package. Your credit card will thank you for it.
  • Flying during the busy season means costly airfares. Try to plan your vacation outside of popular dates, such as Christmas, New Year's Eve and Easter.

How long is a flight to Lexington?
Your city of origin, which airport you leave from and if you travel nonstop — the flight duration depends on lots of things. But we've listed the average times for some of the most well-known routes to Lexington:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 44 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 34 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Logan Intl. Airport (BOS) - 1 hour and 17 minutes

What is the best time to book a flight to Lexington?
Generally speaking, January is the best time to book your airfare. This is followed by February and August. Keep this in mind while you search for a cheap flight to Lexington.
What day of the week is the cheapest to book a flight to Lexington?
If you're after inexpensive fares to Lexington, the best days of the week to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a fabulous flight deal will be all yours.
What is the cheapest day of the week to fly to Lexington?
According to Orbitz data from 2020, Monday is normally the best day to nab cheap flights to Lexington. Tuesday also offers budget-friendly airfares, while Saturday has the highest ticket rates. Although leaving at the weekend can be more suitable, you'll have more money to play with if you fly out early in the week.
What is the cheapest month to fly to Lexington?
We won't keep you guessing — according to Orbitz data, August is generally the most affordable month to fly. Perfect for those who want to sneak in a weekend getaway or just an escape from it all before the weather turns. Be aware that the most expensive time to fly is in the middle of summer, with airfares peaking in June.
Which airlines allow free cancellation?
If you think your travel plans could change, Orbitz can help you find a flexible fare. All you have to do is choose "Filter by flexible change policies" when searching for your perfect flight. We'll show you airlines that offer free cancellation and no change fees — in addition to our awesome low prices.
What do I need for the flight to Lexington?
Nothing's more fun than jetting somewhere new, but it pays to be prepared. These practical tips will help get your journey off to a flying start:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any hassles during check-in, make sure that the personal information on your ticket is correct and matches your government-issued photo ID.
  • Make time fly by even faster on your short hop by packing the right things. Think a water bottle, snacks and entertainment. If you want your trip to Lexington to pass nice and peacefully, throw some headphones in your carry-on bag too.
  • No matter what the temperature is doing outside, plane cabins can get cold. Take a hoodie on board to keep yourself comfortable.

How many direct flights are there to Lexington?
You can jump aboard one of 1,287 flights that travel direct to Lexington each month. JetBlue Airways, Delta Air Lines and American Airlines are just some of the airlines that will take you there comfortably in one go. Cape Air, United Airlines and Southwest Airlines are some other carriers that fly to Lexington nonstop.
How do I get cheap first-class/business deals to Lexington?
If you think a first or business-class ticket is out of your reach, you may want to think again. Here are some tips to help you nab a premium flight to Lexington for less:

  • Be flexible. By being open to other travel dates, you'll have more chances of finding a deal on first or business-class airfares.
  • Search for a budget airline that has seats in business class. They often come with more space and a glass of Champagne — but without the high price.
  • Bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat at the front of the plane. You can also try upgrading with points earned through a loyalty program.

How to get into Lexington from the airport?
Make things more convenient with a Logan Intl. Airport (BOS) car rental. Arrive at Logan Intl. Airport (BOS) and then grab some wheels from one of the two outlets on-site. Enterprise and Advantage Rent-A-Car both have a great variety of cars to choose from. Once the keys are in your hand, you'll need to travel around 12 miles to the northwest to get to the excitement of central Lexington. Renting a vehicle from downtown is another option with great deals from Lexington car rentals.
What is the best time to go to Lexington?
If you want to soak up the unique vibe of Lexington in the peak season, March, April and May are the prime months to visit. June 20 signals the onset of summer in the Northern Hemisphere and is a perfect time to go if you enjoy the outdoors. Around this time of the year, average daily temperatures usually range from 60 ºF to 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.