$268+ Cheap flights from Boston to Hilton Head Island (BOS - HHH)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Oct 5 — Oct 121
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Hilton Head Island with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Hilton Head Island
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to Hilton Head IslandExplore the most affordable flight options available from Boston to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
Explore the most affordable flight options available from Boston to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
1 stop4h 25m
Tue 10/1312:29 pm -
1 stop5h 27m
Deal found 9/1![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:54 am -
1 stop4h 51m
Wed 10/72:56 pm -
2 stops8h 29m
Deal found 9/5![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:05 am -
1 stop6h 22m
Tue 9/224:17 pm -
1 stop6h 09m
Deal found 8/31![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
1 stop4h 43m
Wed 10/214:13 pm -
1 stop7h 07m
Deal found 9/4![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop8h 10m
Sat 10/102:51 pm -
2 stops9h 08m
Deal found 9/3![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
1 stop4h 43m
Wed 10/214:13 pm -
1 stop6h 11m
Deal found 9/3![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop6h 37m
Sat 10/246:13 pm -
1 stop4h 38m
Deal found 9/4![American Airlines logo]()
$353
Best flights from Boston to Hilton Head IslandDiscover carefully curated flight deals from Boston to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
Discover carefully curated flight deals from Boston to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:38 am -
1 stop4h 57m
Sat 10/102:51 pm -
1 stop8h 34m
Deal found 9/3![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am -
2 stops9h 27m
Mon 9/144:17 pm -
1 stop7h 00m
Deal found 8/31![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:00 am -
2 stops7h 21m
Mon 11/912:25 pm -
2 stops9h 21m
Deal found 9/5![American Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:00 am -
1 stop7h 27m
Tue 9/2212:17 pm -
2 stops8h 09m
Deal found 8/31![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:45 am -
2 stops8h 18m
Sat 9/122:48 pm -
1 stop7h 11m
Deal found 9/4![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
1 stop5h 29m
Thu 9/244:17 pm -
1 stop6h 09m
Deal found 9/3![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop6h 35m
Sat 10/242:51 pm -
2 stops9h 08m
Deal found 9/3![United Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:45 am -
2 stops8h 18m
Mon 9/141:50 pm -
2 stops10h 09m
Deal found 8/31![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:38 am -
1 stop4h 57m
Sat 10/32:51 pm -
2 stops9h 08m
Deal found 9/4![United Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:05 am -
1 stop6h 58m
Sat 9/261:16 pm -
1 stop6h 09m
Deal found 9/3![United Airlines logo]()
$549
Last-minute flights from Boston to Hilton Head IslandDiscover last-minute flight deals from Boston to Hilton Head Island. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Hilton Head Island. Data last updated September 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:05 am -
1 stop6h 10m
Tue 9/2911:07 am -
1 stop5h 48m
Deal found 9/3![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:54 am -
1 stop4h 51m
Wed 10/72:56 pm -
2 stops8h 29m
Deal found 9/5![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop8h 10m
Sat 10/102:51 pm -
2 stops9h 08m
Deal found 9/3![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
1 stop4h 25m
Tue 10/1312:29 pm -
1 stop5h 27m
Deal found 9/1![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
1 stop4h 43m
Wed 10/214:13 pm -
1 stop7h 07m
Deal found 9/4![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
1 stop4h 43m
Thu 10/224:13 pm -
1 stop7h 07m
Deal found 9/3![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop6h 37m
Sat 10/246:13 pm -
1 stop4h 38m
Deal found 9/4![American Airlines logo]()
$353
One-way flights from Boston to Hilton Head IslandSearch for one-way flight options from Boston to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
Search for one-way flight options from Boston to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:20 pm -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop5h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:20 pm -
2 stops18h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$280
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:00 am -
1 stop4h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:20 pm -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$290
Find flight deals from Boston to Hilton Head Island
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (American Airlines) |
One-way from | $268 (Delta) |
Popular in | April |
Cheapest in | June |
Average price | $418 |
Good round-trip deal | $463 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 5, 2026.
Use the filters below to find and compare flights from Boston to Hilton Head Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sat 10/3
8:55 am-3:27 pm
1 stop6h 32m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Wed 9/30
7:38 am-12:35 pm
1 stop4h 57m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Thu 10/29
6:00 am-11:43 am
1 stop5h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Mon 9/28
6:00 am-11:29 am
1 stop5h 29m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Wed 9/30
5:40 am-3:27 pm
2 stops9h 47m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Quickest round-trip
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Tue 10/6
7:00 am-11:43 am
1 stop4h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Fri 11/6
7:00 am-11:43 am
1 stop4h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Mon 11/2
6:00 am-11:43 am
1 stop5h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sat 10/31
7:00 am-11:43 am
1 stop4h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sat 10/3
7:38 am-12:35 pm
1 stop4h 57m
Hilton Head Island
Sat 10/10
2:51 pm-11:25 pm
1 stop8h 34m
$319
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Boston to Hilton Head Island
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Hilton Head Island in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Boston-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Hilton Head Island flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Boston to Hilton Head Island
Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Boston with our price prediction graph.
BOS-HHH
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Boston to Hilton Head Island
How far ahead should I book a flight from Boston to Hilton Head Island?
The best time to book flights from Boston to Hilton Head Island is 65 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Boston to Hilton Head Island?
Currently, June is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $314). Flying from Boston to Hilton Head Island in April is currently the most expensive (average of $574). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from BOS to HHH?
Find hourly flight availability from Boston to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 5, 2026.
When flying from Boston to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Hilton Head Island
Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated September 5, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Boston to Hilton Head Island by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Related info for your journey
Find useful and relevant information for your journey from Boston to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
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Complete your trip
Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 5, 2026.
Boston and Hilton Head Island flights
Browse other Boston and Hilton Head Island flight options. Last updated on September 5, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Boston to Hilton Head Island
Discover the top 4 airlines that operate flights from Boston to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$183 | Average$378 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$251 | Average$424 | FlexibilityNo cancel fee | On-time71% |