$59+ Cheap flights from Cleveland (CLE) 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Apr 6 — Apr 131
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Chesapeake with Cheapflights
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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
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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 Cleveland to Chesapeake
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Best
Last-minute
One-way
Cheapest flights from Cleveland to ChesapeakeExplore the most affordable flight options available from Cleveland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 7, 2026.
Explore the most affordable flight options available from Cleveland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Sat 4/187:00 pm
CLE
- ORF
1 stop15h 32m
Frontier
Sat 4/2511:27 am
ORF
- CLE
1 stop6h 28m
Frontier
Deal found 3/7![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:01 pm
CLE
- ORF
1 stop16h 23m
Frontier
Mon 5/1111:19 am
ORF
- CLE
1 stop11h 55m
Frontier
Deal found 3/3![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:55 pm
CLE
- ORF
1 stop13h 22m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop26h 59m
Frontier
Deal found 3/3![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:55 pm
CLE
- ORF
1 stop13h 37m
Frontier
Sat 5/211:27 am
ORF
- CLE
1 stop6h 28m
Frontier
Deal found 3/4![Frontier logo]()
$158
This Expedia deal was found by Cheapflights users on 3/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1710:00 pm
CLE
- ORF
1 stop20h 21m
Frontier
Sun 4/1912:32 pm
ORF
- CLE
1 stop19h 08m
Frontier
Deal found 3/5![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/263:44 pm
CLE
- ORF
1 stop18h 48m
Frontier
Thu 4/3011:27 am
ORF
- CLE
1 stop22h 16m
Frontier
Deal found 3/5![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Mon 4/205:30 am
CLE
- ORF
1 stop11h 37m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop20h 17m
Frontier
Deal found 3/6![Frontier logo]()
$165
Best flights from Cleveland to ChesapeakeDiscover carefully curated flight deals from Cleveland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 7, 2026.
Discover carefully curated flight deals from Cleveland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Thu 4/95:30 am
CLE
- ORF
1 stop5h 06m
Frontier
Mon 4/133:54 pm
ORF
- CLE
2 stops15h 50m
Frontier
Deal found 3/7![Frontier logo]()
$236
This Delta deal was found by Cheapflights users on 3/5. 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.
Wed 4/221:38 pm
CLE
- ORF
1 stop5h 32m
Delta
Wed 4/296:00 am
ORF
- CLE
1 stop6h 55m
Delta
Deal found 3/5![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 3/7. 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 4/116:21 am
CLE
- ORF
1 stop5h 48m
United Airlines
Sat 4/186:11 am
ORF
- CLE
1 stop3h 41m
United Airlines
Deal found 3/7![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 3/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:50 am
CLE
- ORF
1 stop4h 10m
Southwest
Tue 6/211:10 am
ORF
- CLE
2 stops9h 10m
Southwest
Deal found 3/3![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 3/3. 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 3/287:26 pm
CLE
- ORF
1 stop4h 58m
Delta
Tue 4/145:57 pm
ORF
- CLE
1 stop5h 42m
Delta
Deal found 3/3![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 3/3. 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 3/287:26 pm
CLE
- ORF
1 stop4h 58m
Delta
Thu 4/97:03 am
ORF
- CLE
1 stop4h 44m
Delta
Deal found 3/3![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 4/2012:55 pm
CLE
- ORF
2 stops9h 05m
Southwest
Mon 4/272:30 pm
ORF
- CLE
2 stops7h 45m
Southwest
Deal found 3/6![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 3/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:59 pm
CLE
- ORF
1 stop3h 47m
United Airlines
Mon 3/307:55 pm
ORF
- CLE
1 stop4h 04m
United Airlines
Deal found 3/2![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 3/6. 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.
Thu 4/233:45 pm
CLE
- ORF
2 stops7h 10m
Southwest
Mon 4/272:30 pm
ORF
- CLE
2 stops7h 45m
Southwest
Deal found 3/6![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 3/7. 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 7/93:19 pm
CLE
- ORF
2 stops8h 25m
United Airlines
Sun 7/126:05 am
ORF
- CLE
1 stop3h 36m
United Airlines
Deal found 3/7![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 3/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:50 am
CLE
- ORF
2 stops10h 00m
Southwest
Mon 5/112:30 pm
ORF
- CLE
2 stops7h 45m
Southwest
Deal found 3/4![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 3/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/244:30 pm
CLE
- ORF
1 stop6h 20m
Southwest
Sun 5/315:50 am
ORF
- CLE
2 stops8h 05m
Southwest
Deal found 3/4![Southwest logo]()
$332
Last-minute flights from Cleveland to ChesapeakeDiscover last-minute flight deals from Cleveland to Chesapeake. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chesapeake. Data last updated March 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Thu 4/95:30 am
CLE
- ORF
1 stop5h 06m
Frontier
Mon 4/1311:33 am
ORF
- CLE
1 stop20h 11m
Frontier
Deal found 3/7![Frontier logo]()
$175
This Expedia deal was found by Cheapflights users on 3/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1710:00 pm
CLE
- ORF
1 stop20h 21m
Frontier
Sun 4/1912:32 pm
ORF
- CLE
1 stop19h 08m
Frontier
Deal found 3/5![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Sat 4/187:00 pm
CLE
- ORF
1 stop15h 32m
Frontier
Sat 4/2511:27 am
ORF
- CLE
1 stop6h 28m
Frontier
Deal found 3/7![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Mon 4/205:30 am
CLE
- ORF
1 stop11h 37m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop20h 17m
Frontier
Deal found 3/6![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:55 pm
CLE
- ORF
1 stop13h 22m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop26h 59m
Frontier
Deal found 3/3![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:55 pm
CLE
- ORF
1 stop13h 37m
Frontier
Sat 5/211:27 am
ORF
- CLE
1 stop6h 28m
Frontier
Deal found 3/4![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/263:44 pm
CLE
- ORF
1 stop18h 48m
Frontier
Thu 4/3011:27 am
ORF
- CLE
1 stop22h 16m
Frontier
Deal found 3/5![Frontier logo]()
$161
One-way flights from Cleveland to ChesapeakeSearch for one-way flight options from Cleveland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
Search for one-way flight options from Cleveland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Trip.com deal was found by Cheapflights users on 3/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:01 pm
CLE
- ORF
1 stop16h 23m
Frontier
Deal found 3/3![Frontier logo]()
$59
This Priceline deal was found by Cheapflights users on 3/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:51 am
CLE
- ORF
1 stop8h 58m
Frontier
Deal found 3/7![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:25 pm
CLE
- ORF
2 stops37h 59m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Tue 3/314:40 pm
CLE
- ORF
1 stop27h 06m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$112
Find flight deals from Cleveland to Chesapeake
Keep the following information in mind while searching for Cleveland to Chesapeake flight deals. Data was last updated March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $126 (Kiwi.com) |
One-way from | $59 (Trip.com) |
Popular in | March |
Cheapest in | August |
Average price | $437 |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland 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 March 7, 2026.
Use the filters below to find and compare flights from Cleveland to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 4/9
5:30 am-10:36 am
1 stop5h 06m
Norfolk
Mon 4/13
3:54 pm-7:44 am
2 stops15h 50m
$236
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Wed 4/22
1:38 pm-7:10 pm
1 stop5h 32m
Norfolk
Wed 4/29
6:00 am-12:55 pm
1 stop6h 55m
$255
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sat 3/28
7:26 pm-12:24 am
1 stop4h 58m
Norfolk
Tue 4/14
5:57 pm-11:39 pm
1 stop5h 42m
$282
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sat 4/11
6:21 am-12:09 pm
1 stop5h 48m
Norfolk
Sat 4/18
6:11 am-9:52 am
1 stop3h 41m
$283
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sat 3/28
7:26 pm-12:24 am
1 stop4h 58m
Norfolk
Thu 4/9
7:03 am-11:47 am
1 stop4h 44m
$289
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Wed 5/20
5:50 am-10:00 am
1 stop4h 10m
Norfolk
Tue 6/2
11:10 am-8:20 pm
2 stops9h 10m
$290
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Mon 4/20
12:55 pm-10:00 pm
2 stops9h 05m
Norfolk
Mon 4/27
2:30 pm-10:15 pm
2 stops7h 45m
$319
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 4/23
3:45 pm-10:55 pm
2 stops7h 10m
Norfolk
Mon 4/27
2:30 pm-10:15 pm
2 stops7h 45m
$319
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Wed 5/6
5:50 am-3:50 pm
2 stops10h 00m
Norfolk
Mon 5/11
2:30 pm-10:15 pm
2 stops7h 45m
$328
Quickest round-trip
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Mon 3/23
7:59 pm-11:46 pm
1 stop3h 47m
Norfolk
Mon 3/30
7:55 pm-11:59 pm
1 stop4h 04m
$329
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Cleveland to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Cleveland with our price prediction graph.
CLE-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 Cleveland to Chesapeake
CLE-C6E
CLE-ORF
How far ahead should I book a flight from Cleveland to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Chesapeake. Price data was last updated on March 6, 2026.
The price you pay for your flight from Cleveland to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 65 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Cleveland to Chesapeake?
Currently, August is the cheapest month in which you can book a flight from Cleveland to Chesapeake (average of $56). Flying from Cleveland to Chesapeake in July is currently the most expensive (average of $118). 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.
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 March 7, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Cleveland to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Cleveland to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Cleveland and Chesapeake flights
Browse other Cleveland and Chesapeake flight options. Last updated on March 7, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on March 7, 2026.
Popular flight searches
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Cleveland to Chesapeake flights
Consider these flights traveling from Cleveland to Chesapeake.
Top 5 airlines flying from Cleveland to Chesapeake
Discover the top 5 airlines that operate flights from Cleveland 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 March 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$290 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$307 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$327 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$204 | Average$354 | FlexibilityNo cancel fee | On-time69% |