$133+ Cheap flights from O'Hare Intl (ORD) to Grand Cayman
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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jun 24 — Jul 11
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Grand Cayman 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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Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to Grand CaymanExplore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
Explore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
This Expedia deal was found by Cheapflights users on 5/20. 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.
Sat 6/61:55 pm
ORD
- GCM
2 stops45h 30m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
1 stop21h 05m
Air Canada
Deal found 5/20![Air Canada logo]()
$383
This Air Canada deal was found by Cheapflights users on 5/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:35 pm
ORD
- GCM
1 stop16h 25m
Air Canada
Mon 6/112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/22![Air Canada logo]()
$395
This Air Canada deal was found by Cheapflights users on 5/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:35 pm
ORD
- GCM
1 stop17h 55m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/23![Air Canada logo]()
$407
This Orbitz deal was found by Cheapflights users on 5/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 9/2612:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 5/24![Air Canada logo]()
$410
This Air Canada deal was found by Cheapflights users on 5/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:40 pm
ORD
- GCM
2 stops19h 50m
Air Canada
Sat 10/1712:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/24![Air Canada logo]()
$413
This Expedia deal was found by Cheapflights users on 5/23. 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 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/812:25 pm
GCM
- ORD
1 stop28h 34m
Air Canada
Deal found 5/23![Air Canada logo]()
$415
This FlightHub deal was found by Cheapflights users on 5/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:40 pm
ORD
- GCM
1 stop13h 05m
Air Canada
Sat 8/810:40 am
GCM
- ORD
1 stop22h 20m
Air Canada
Deal found 5/24![Air Canada logo]()
$421
Best flights from O'Hare Intl to Grand CaymanDiscover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
Discover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
This United Airlines deal was found by Cheapflights users on 5/24. 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 8/35:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Fri 8/71:35 pm
GCM
- ORD
1 stop9h 40m
United Airlines
Deal found 5/24![United Airlines logo]()
$661
This American Airlines deal was found by Cheapflights users on 5/24. 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.
Mon 8/36:37 am
ORD
- GCM
2 stops9h 33m
American Airlines
Fri 8/712:00 pm
GCM
- ORD
2 stops10h 30m
American Airlines
Deal found 5/24![American Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 5/22. 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 6/235:22 pm
ORD
- GCM
2 stops18h 12m
Delta
Tue 6/3012:59 pm
GCM
- ORD
2 stops21h 51m
Delta
Deal found 5/22![Delta logo]()
$686
This Delta deal was found by Cheapflights users on 5/24. 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 7/275:30 am
ORD
- GCM
1 stop6h 01m
Delta
Sun 8/212:56 pm
GCM
- ORD
1 stop7h 37m
Delta
Deal found 5/24![Delta logo]()
$696
This United Airlines deal was found by Cheapflights users on 5/20. 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 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 7/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/20![United Airlines logo]()
$717
This Delta deal was found by Cheapflights users on 5/22. 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 7/295:30 am
ORD
- GCM
1 stop6h 01m
Delta
Sun 8/212:56 pm
GCM
- ORD
1 stop7h 37m
Delta
Deal found 5/22![Delta logo]()
$696
This United Airlines deal was found by Cheapflights users on 5/24. 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 7/69:40 pm
ORD
- GCM
1 stop14h 50m
United Airlines
Sat 7/111:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/24![United Airlines logo]()
$736
This United Airlines deal was found by Cheapflights users on 5/21. 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 6/175:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Sun 6/211:35 pm
GCM
- ORD
1 stop8h 16m
United Airlines
Deal found 5/21![United Airlines logo]()
$751
This Delta deal was found by Cheapflights users on 5/22. 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 6/175:30 am
ORD
- GCM
1 stop6h 04m
Delta
Tue 6/3012:59 pm
GCM
- ORD
2 stops21h 51m
Delta
Deal found 5/22![Delta logo]()
$771
Last-minute flights from O'Hare Intl to Grand CaymanDiscover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated May 25, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 5/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:35 pm
ORD
- GCM
1 stop16h 25m
Air Canada
Mon 6/112:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 5/22![Air Canada logo]()
$395
This Mytrip deal was found by Cheapflights users on 5/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:55 am
ORD
- GCM
1 stop25h 30m
Multiple Airlines
Tue 6/91:45 pm
GCM
- ORD
2 stops20h 33m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$557
This Expedia deal was found by Cheapflights users on 5/23. 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 6/58:20 pm
ORD
- GCM
1 stop13h 40m
Air Canada
Mon 6/812:25 pm
GCM
- ORD
1 stop28h 34m
Air Canada
Deal found 5/23![Air Canada logo]()
$415
This Expedia deal was found by Cheapflights users on 5/20. 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.
Sat 6/61:55 pm
ORD
- GCM
2 stops45h 30m
Air Canada
Sat 6/1310:55 am
GCM
- ORD
1 stop21h 05m
Air Canada
Deal found 5/20![Air Canada logo]()
$383
This Orbitz deal was found by Cheapflights users on 5/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:15 am
ORD
- GCM
2 stops30h 30m
Multiple Airlines
Mon 6/1512:25 pm
GCM
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$569
This FlightHub deal was found by Cheapflights users on 5/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Sat 7/42:10 pm
GCM
- ORD
1 stop26h 06m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$584
One-way flights from O'Hare Intl to Grand CaymanSearch for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
Search for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This Orbitz deal was found by Cheapflights users on 5/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
- GCM
1 stop13h 20m
Air Canada
Deal found 5/23![Air Canada logo]()
$133
This Air Canada deal was found by Cheapflights users on 5/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:25 pm
ORD
- GCM
1 stop15h 00m
Air Canada
Deal found 5/24![Air Canada logo]()
$138
This Travelocity deal was found by Cheapflights users on 5/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:04 pm
ORD
- GCM
2 stops41h 21m
Air Canada
Deal found 5/24![Air Canada logo]()
$141
This Air Canada deal was found by Cheapflights users on 5/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:20 pm
ORD
- GCM
1 stop15h 05m
Air Canada
Deal found 5/22![Air Canada logo]()
$146
This Travelocity deal was found by Cheapflights users on 5/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/123:45 pm
ORD
- GCM
1 stop19h 40m
Air Canada
Deal found 5/23![Air Canada logo]()
$157
This Air Canada deal was found by Cheapflights users on 5/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Deal found 5/23![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 5/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:45 am
ORD
- GCM
2 stops25h 00m
Air Canada
Deal found 5/24![Air Canada logo]()
$165
This Travelocity deal was found by Cheapflights users on 5/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:45 pm
ORD
- GCM
1 stop18h 15m
Air Canada
Deal found 5/21![Air Canada logo]()
$193
This Travelocity deal was found by Cheapflights users on 5/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:45 am
ORD
- GCM
2 stops49h 15m
Air Canada
Deal found 5/21![Air Canada logo]()
$196
This Air Canada deal was found by Cheapflights users on 5/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:22 pm
ORD
- GCM
1 stop12h 23m
Air Canada
Deal found 5/21![Air Canada logo]()
$198
Find flight deals from O'Hare Intl to Grand Cayman
Keep the following information in mind while searching for O'Hare Intl to Grand Cayman flight deals. Data was last updated May 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $383 (Expedia) |
One-way from | $133 (Orbitz) |
Popular in | December |
Cheapest in | February |
Average price | $700 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Grand Cayman 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 May 25, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 8/3
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Fri 8/7
1:35 pm-11:15 pm
1 stop9h 40m
$661
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 8/3
6:37 am-4:10 pm
2 stops9h 33m
George Town Owen Roberts Intl
Fri 8/7
12:00 pm-10:30 pm
2 stops10h 30m
$666
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 6/23
5:22 pm-11:34 am
2 stops18h 12m
George Town Owen Roberts Intl
Tue 6/30
12:59 pm-10:50 am
2 stops21h 51m
$686
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 7/27
5:30 am-11:31 am
1 stop6h 01m
George Town Owen Roberts Intl
Sun 8/2
12:56 pm-8:33 pm
1 stop7h 37m
$696
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 7/29
5:30 am-11:31 am
1 stop6h 01m
George Town Owen Roberts Intl
Sun 8/2
12:56 pm-8:33 pm
1 stop7h 37m
$696
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 7/18
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
Sat 7/25
1:50 pm-6:13 pm
Nonstop4h 23m
$717
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 7/6
9:40 pm-12:30 pm
1 stop14h 50m
George Town Owen Roberts Intl
Sat 7/11
1:50 pm-6:13 pm
Nonstop4h 23m
$736
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 6/17
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Sun 6/21
1:35 pm-9:51 pm
1 stop8h 16m
$751
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 6/17
5:30 am-11:34 am
1 stop6h 04m
George Town Owen Roberts Intl
Tue 6/30
12:59 pm-10:50 am
2 stops21h 51m
$771
Cheapest one-way
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 11/18
6:30 pm-12:00 pm
1 stop16h 30m
$213
Showing 1-10 of 19 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from O'Hare Intl with our price prediction graph.
ORD-GCM
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 Chicago O'Hare Intl Airport to Grand Cayman
ORD-zzLAW
ORD-GCM
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $174). Flying from Chicago O'Hare Intl Airport to Grand Cayman in September is currently the most expensive (average of $659). 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 ORD to LAW?
Find hourly flight availability from O'Hare Intl to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 25, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Grand Cayman as you normally would.
Reviews of airlines servicing Grand Cayman
Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated May 25, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Entertainment
7.1
Crew
8.1
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Entertainment
7.1
Crew
8.1
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Comfort
7.3
Entertainment
7.1
Crew
8.1
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Grand Cayman. 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 to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Grand Cayman by cabin class
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O'Hare Intl and Grand Cayman flights
Browse other O'Hare Intl and Grand Cayman flight options. Last updated on May 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from O'Hare Intl to Grand Cayman
Discover the top 2 airlines that operate flights from O'Hare Intl to Grand Cayman. 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 May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$608 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$675 | FlexibilityNo cancel fee | On-time71% |