$205+ Cheap flights from Oakland, CA (OAK) to Chesapeake, VA
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
5月 31 — 6月 71
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Chesapeake 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 Oakland to Chesapeake
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Best
Last-minute
One-way
Cheapest flights from Oakland to ChesapeakeExplore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5月 1, 2026.
Explore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5月 1, 2026.
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 7/82:35 pm
OAK
- ORF
1 stop7h 10m
Southwest
週三 7/295:15 am
ORF
- OAK
1 stop7h 30m
Southwest
Deal found 4/29![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 7/235:30 am
OAK
- ORF
2 stops14h 55m
Southwest
週二 7/284:30 pm
ORF
- OAK
2 stops9h 50m
Southwest
Deal found 4/27![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 8/811:55 pm
OAK
- ORF
1 stop9h 10m
Southwest
週六 8/156:00 am
ORF
- OAK
2 stops9h 50m
Southwest
Deal found 4/27![Southwest logo]()
$439
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 7/1211:55 pm
OAK
- ORF
1 stop7h 50m
Southwest
週日 7/265:10 pm
ORF
- OAK
1 stop9h 15m
Southwest
Deal found 5/1![Southwest logo]()
$583
This Delta deal was found by Cheapflights users on 4/28. 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.
週四 7/95:05 pm
OAK
- ORF
2 stops27h 27m
Delta
週三 7/226:05 am
ORF
- OAK
2 stops20h 45m
Delta
Deal found 4/28![Delta logo]()
$687
This Delta deal was found by Cheapflights users on 4/28. 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.
週二 7/76:00 am
OAK
- ORF
2 stops26h 22m
Delta
週一 7/276:17 pm
ORF
- OAK
2 stops32h 33m
Delta
Deal found 4/28![Delta logo]()
$712
This Delta deal was found by Cheapflights users on 4/28. 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.
週二 7/76:00 am
OAK
- ORF
2 stops24h 09m
Delta
週五 7/176:05 am
ORF
- OAK
2 stops13h 16m
Delta
Deal found 4/28![Delta logo]()
$719
Best flights from Oakland to ChesapeakeDiscover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 5月 1, 2026.
Discover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 5月 1, 2026.
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 7/235:30 am
OAK
- ORF
2 stops14h 55m
Southwest
週二 7/284:30 pm
ORF
- OAK
2 stops9h 50m
Southwest
Deal found 4/27![Southwest logo]()
$425
This Delta deal was found by Cheapflights users on 4/28. 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.
週一 5/115:05 pm
OAK
- ORF
2 stops12h 57m
Delta
週三 5/134:39 pm
ORF
- OAK
2 stops10h 18m
Delta
Deal found 4/28![Delta logo]()
$712
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 8/811:55 pm
OAK
- ORF
1 stop9h 10m
Southwest
週六 8/156:25 am
ORF
- OAK
2 stops11h 30m
Southwest
Deal found 4/27![Southwest logo]()
$439
This Delta deal was found by Cheapflights users on 4/28. 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.
週一 7/135:05 pm
OAK
- ORF
2 stops20h 16m
Delta
週二 7/285:15 am
ORF
- OAK
2 stops21h 35m
Delta
Deal found 4/28![Delta logo]()
$719
This Delta deal was found by Cheapflights users on 4/28. 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.
週二 7/712:30 pm
OAK
- ORF
2 stops17h 39m
Delta
週四 7/2310:16 am
ORF
- OAK
2 stops16h 34m
Delta
Deal found 4/28![Delta logo]()
$719
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 7/125:10 am
OAK
- ORF
2 stops15h 45m
Southwest
週日 7/266:20 am
ORF
- OAK
2 stops8h 55m
Southwest
Deal found 5/1![Southwest logo]()
$779
This Delta deal was found by Cheapflights users on 4/28. 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.
週一 7/135:05 pm
OAK
- ORF
2 stops27h 27m
Delta
週日 7/2612:43 pm
ORF
- OAK
2 stops14h 07m
Delta
Deal found 4/28![Delta logo]()
$737
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 5/1111:55 pm
OAK
- ORF
2 stops9h 00m
Southwest
週三 5/136:25 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 4/28![Southwest logo]()
$779
Last-minute flights from Oakland to ChesapeakeDiscover last-minute flight deals from Oakland to Chesapeake. Data last updated 5月 1, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chesapeake. Data last updated 5月 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/65:50 am
OAK
- ORF
1 stop12h 20m
Southwest
週三 5/1311:10 am
ORF
- OAK
2 stops10h 40m
Southwest
Deal found 4/29![Southwest logo]()
$758
This Delta deal was found by Cheapflights users on 4/28. 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.
週六 5/95:55 pm
OAK
- ORF
2 stops14h 25m
Delta
週三 5/134:39 pm
ORF
- OAK
2 stops10h 18m
Delta
Deal found 4/28![Delta logo]()
$712
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 5/910:10 am
OAK
- ORF
2 stops9h 55m
Southwest
週三 5/136:25 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 4/28![Southwest logo]()
$779
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 5/106:05 am
OAK
- ORF
1 stop8h 20m
Southwest
週三 5/136:25 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 4/28![Southwest logo]()
$747
This Delta deal was found by Cheapflights users on 4/29. 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.
週三 5/1312:28 pm
OAK
- ORF
2 stops23h 59m
Delta
週六 5/239:20 am
ORF
- OAK
2 stops16h 14m
Delta
Deal found 4/29![Delta logo]()
$746
This Delta deal was found by Cheapflights users on 4/29. 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.
週三 5/1312:28 pm
OAK
- ORF
2 stops17h 34m
Delta
週日 5/249:25 am
ORF
- OAK
2 stops10h 00m
Delta
Deal found 4/29![Delta logo]()
$789
This Delta deal was found by Cheapflights users on 4/29. 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.
週五 5/155:05 pm
OAK
- ORF
2 stops20h 18m
Delta
週日 5/249:25 am
ORF
- OAK
2 stops10h 00m
Delta
Deal found 4/29![Delta logo]()
$800
This Delta deal was found by Cheapflights users on 4/29. 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.
週五 5/155:05 pm
OAK
- ORF
2 stops20h 18m
Delta
週六 5/2312:00 pm
ORF
- OAK
2 stops26h 48m
Delta
Deal found 4/29![Delta logo]()
$810
This Delta deal was found by Cheapflights users on 4/29. 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.
週六 5/165:55 pm
OAK
- ORF
2 stops20h 26m
Delta
週六 5/235:20 am
ORF
- OAK
2 stops20h 14m
Delta
Deal found 4/29![Delta logo]()
$770
This Delta deal was found by Cheapflights users on 4/29. 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.
週六 5/166:00 am
OAK
- ORF
2 stops14h 20m
Delta
週日 5/246:00 am
ORF
- OAK
2 stops19h 34m
Delta
Deal found 4/29![Delta logo]()
$808
One-way flights from Oakland to ChesapeakeSearch for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated 5月 1, 2026.
Search for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated 5月 1, 2026.
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 7/812:35 pm
OAK
- ORF
1 stop9h 10m
Southwest
Deal found 4/28![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 5/1511:55 pm
OAK
- ORF
1 stop7h 55m
Southwest
Deal found 4/30![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 4/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/1310:15 am
OAK
- ORF
2 stops8h 40m
Southwest
Deal found 4/26![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 4/28. 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.
週三 9/95:05 pm
OAK
- ORF
2 stops14h 31m
Delta
Deal found 4/28![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 5/2211:55 pm
OAK
- ORF
1 stop7h 55m
Southwest
Deal found 4/29![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 5/145:55 am
OAK
- ORF
1 stop13h 05m
Southwest
Deal found 4/30![Southwest logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 5/148:22 pm
OAK
- ORF
3 stops45h 42m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 5/158:22 pm
OAK
- ORF
3 stops21h 42m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 7/711:15 pm
OAK
- ORF
3 stops54h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 5/228:22 pm
OAK
- ORF
3 stops21h 42m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$504
Find flight deals from Oakland to Chesapeake
Keep the following information in mind while searching for Oakland to Chesapeake flight deals. Data was last updated 5月 1, 2026.
Round-trip from | $409 (Southwest) |
|---|---|
One-way from | $205 (Southwest) |
Popular in | April |
Cheapest in | February |
Average price | $840 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Chesapeake 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 2,558,603 searches. Data last updated 5月 1, 2026.
Use the filters below to find and compare flights from Oakland to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週四 7/23
5:30 am-11:25 pm
2 stops14h 55m
Norfolk
週二 7/28
4:30 pm-11:20 pm
2 stops9h 50m
$425
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週六 8/8
11:55 pm-12:05 pm
1 stop9h 10m
Norfolk
週六 8/15
6:25 am-2:55 pm
2 stops11h 30m
$439
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週一 5/11
5:05 pm-9:02 am
2 stops12h 57m
Norfolk
週三 5/13
4:39 pm-11:57 pm
2 stops10h 18m
$712
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週一 7/13
5:05 pm-4:21 pm
2 stops20h 16m
Norfolk
週二 7/28
5:15 am-11:50 pm
2 stops21h 35m
$719
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週二 7/7
12:30 pm-9:09 am
2 stops17h 39m
Norfolk
週四 7/23
10:16 am-11:50 pm
2 stops16h 34m
$719
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週一 7/13
5:05 pm-11:32 pm
2 stops27h 27m
Norfolk
週日 7/26
12:43 pm-11:50 pm
2 stops14h 07m
$737
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週日 7/12
5:10 am-11:55 pm
2 stops15h 45m
Norfolk
週日 7/26
6:20 am-12:15 pm
2 stops8h 55m
$779
Quickest round-trip
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週一 5/11
11:55 pm-11:55 am
2 stops9h 00m
Norfolk
週三 5/13
6:25 pm-11:25 pm
1 stop8h 00m
$779
Cheapest one-way
Quickest one-way
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週二 7/7
11:55 pm-10:45 am
1 stop7h 50m
$205
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
週一 9/7
11:55 pm-12:05 pm
1 stop9h 10m
$205
Showing 1-10 of 15 resultsSorted by cheapest first
Best time to book a flight from Oakland to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Oakland with our price prediction graph.
OAK-ORF
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 Oakland to Chesapeake
OAK-C6E
OAK-ORF
How much does it cost to fly round-trip from Oakland, California to Chesapeake?
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated 5月 1, 2026.
See what other customers who have flown with Southwest from Oakland to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from Oakland to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
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Popular flights
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Alternative routes for Oakland to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Chesapeake by cabin class
Find flights from Oakland to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Chesapeake flights
Browse other Oakland and Chesapeake flight options. Last updated on 5月 1, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on 5月 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Chesapeake flights
Consider these flights traveling from Oakland to Chesapeake.
Top airline flying from Oakland to Chesapeake
Discover the top airline that operate flights from Oakland to Chesapeake. 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 2,558,603 searches. Data last updated 5月 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$283 | Average$512 | FlexibilityNo cancel fee | On-time63% |