Cheap flights To Lexington (BOS) from $44

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Cheap Flights to Lexington from $44 One Way, $102 Round Trip

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

Sat, Oct 11 - Sat, Oct 11
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 11 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 11, priced at $102 just found
Sat, Aug 30 - Wed, Sep 3
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 3 hours ago
$103
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Wed, Sep 3, priced at $103 found 3 hours ago
Wed, Oct 15 - Wed, Nov 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 15 from Orlando Intl. to Portsmouth Intl., returning Wed, Nov 5, priced at $107 found 1 day ago
Sat, Jul 19 - Sat, Jul 26
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Jul 19 from Orlando Intl. to Portsmouth Intl., returning Sat, Jul 26, priced at $107 found 1 hour ago
Sat, Jul 26 - Sat, Aug 2
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Jul 26 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 2, priced at $109 found 6 days ago
Sat, Jul 12 - Sat, Jul 19
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jul 12 from Orlando Intl. to Portsmouth Intl., returning Sat, Jul 19, priced at $111 found 2 days ago
Sat, Aug 2 - Sat, Aug 9
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Aug 2 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 9, priced at $112 just found
Sat, Jul 12 - Mon, Jul 21
MCO
Orlando Intl.
BOS
Logan Intl.
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jul 12 from Orlando Intl. to Logan Intl., returning Mon, Jul 21, priced at $113 found 1 hour ago
Sat, Jul 12 - Sat, Jul 12
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jul 12 from Orlando Intl. to Portsmouth Intl., returning Sat, Jul 12, priced at $115 found 2 days ago
Sat, Jul 12 - Sat, Jul 19
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$116 Roundtrip, found 2 days ago
$116
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jul 12 from Orlando Intl. to Portsmouth Intl., returning Sat, Jul 19, priced at $116 found 2 days ago

Lexington Flight Information

Traveling To
Lexington
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines, Breeze Airways, Frontier Airlines
Flight Price
$102
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 Beverly
3.0-star property

The Beverly

Aug 28 - Aug 31

3 night stay

Chicago (ORD) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach
Save 100% on your flight
per person
found 1 day ago
Riverview Resort
3.0-star property

Riverview Resort

Aug 17 - Aug 20

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Encore Boston Harbor
5.0-star property

Encore Boston Harbor

Aug 11 - Aug 14

3 night stay

Los Angeles (LAX) to Boston (BOS)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 24 hours ago
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See all available trips from Chicago to Lexington
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Lexington first class flight packages

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

citizenM Boston North Station

9.2/10 Wonderful! (3,460 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Perfect Location!!! Walking distance from almost everything.

Reviewed on Jun 4, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

9.6/10 Exceptional! (242 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
The heater in Room 37 did not maintain a steady, dependable temperature (it varied \- by 5 degrees F). Otherwise, superb restaurant onsite and superb continental breakfast.

Reviewed on Feb 13, 2025

Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

8.8/10 Excellent! (1,002 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Valet parking rate of $72/night was excessive. Other than that, the room was lovely and comfortable for our family of 5, staff was responsive and friendly. Gym is well equipped with nice views. Very convenient to get to Logan airport from this hotel.

Reviewed on Apr 14, 2025

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See all available trips from Chicago to Lexington
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Lexington

Snag some “suite” deals when you add cheap hotel rooms to Lexington flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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While shopping Orbitz sales on Lexington flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Lexington flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Lexington. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $102 to $116. But it was passengers departing from Orlando (MCO) who nabbed the biggest bargains. One-way tickets to Lexington started at just $44.
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.

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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.