$287+ Cheap flights from Illinois to Basseterre (SKB)
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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Mar 6 — Mar 131
1 adult, Economy
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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
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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 Illinois to Basseterre
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Cheapest flights from Illinois to BasseterreExplore the most affordable flight options available from Illinois to Basseterre. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Illinois to Basseterre. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 3/36:59 pm
ORD
- SKB
1 stop17h 23m
American Airlines
Tue 3/102:24 pm
SKB
- ORD
1 stop9h 53m
American Airlines
Deal found 2/1![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 3/56:59 pm
ORD
- SKB
1 stop17h 23m
American Airlines
Thu 3/122:24 pm
SKB
- ORD
1 stop11h 14m
American Airlines
Deal found 2/3![American Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 5/167:00 pm
ORD
- SKB
1 stop17h 30m
American Airlines
Thu 5/212:40 pm
SKB
- ORD
1 stop8h 39m
American Airlines
Deal found 2/3![American Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 2/4. 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.
Sat 4/185:10 am
ORD
- SKB
1 stop8h 00m
Delta
Sat 4/251:55 pm
SKB
- ORD
1 stop11h 04m
Delta
Deal found 2/4![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 2/4. 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.
Sat 4/186:00 am
MDW
- SKB
1 stop7h 10m
Delta
Sat 4/251:55 pm
SKB
- MDW
1 stop9h 33m
Delta
Deal found 2/4![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 2/1. 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.
Fri 3/612:29 pm
ORD
- SKB
2 stops23h 04m
Delta
Sat 3/141:50 pm
SKB
- ORD
1 stop11h 04m
Delta
Deal found 2/1![Delta logo]()
$608
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 9/127:16 pm
ORD
- SKB
1 stop17h 04m
American Airlines
Sat 9/192:45 pm
SKB
- ORD
1 stop8h 43m
American Airlines
Deal found 2/3![American Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 3/115:00 am
ORD
- SKB
1 stop7h 24m
American Airlines
Mon 3/162:24 pm
SKB
- ORD
1 stop11h 14m
American Airlines
Deal found 2/3![American Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 4/188:46 pm
ORD
- SKB
2 stops15h 44m
American Airlines
Sat 4/254:50 pm
SKB
- ORD
1 stop8h 35m
American Airlines
Deal found 2/1![American Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 5/16:55 pm
STL
- SKB
1 stop17h 05m
American Airlines
Wed 5/62:32 pm
SKB
- STL
1 stop8h 52m
American Airlines
Deal found 2/3![American Airlines logo]()
$659
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:55 pm
STL
- SKB
2 stops17h 35m
American Airlines
Sat 5/22:32 pm
SKB
- STL
2 stops18h 58m
American Airlines
Deal found 2/2![American Airlines logo]()
$679
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:20 pm
STL
- SKB
1 stop18h 01m
American Airlines
Fri 4/102:32 pm
SKB
- STL
1 stop8h 52m
American Airlines
Deal found 2/2![American Airlines logo]()
$747
Best flights from Illinois to BasseterreDiscover carefully curated flight deals from Illinois to Basseterre that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Illinois to Basseterre that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This American Airlines deal was found by Cheapflights users on 2/4. 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 3/37:40 pm
ORD
- SKB
1 stop16h 42m
American Airlines
Tue 3/102:24 pm
SKB
- ORD
1 stop9h 53m
American Airlines
Deal found 2/4![American Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 2/1. 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.
Sat 4/186:00 am
MDW
- SKB
1 stop7h 10m
Delta
Sat 4/251:55 pm
SKB
- MDW
1 stop9h 33m
Delta
Deal found 2/1![Delta logo]()
$603
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 4/46:59 pm
ORD
- SKB
1 stop17h 22m
American Airlines
Sat 4/114:50 pm
SKB
- ORD
1 stop8h 35m
American Airlines
Deal found 2/1![American Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 3/58:58 pm
ORD
- SKB
2 stops15h 24m
American Airlines
Thu 3/122:24 pm
SKB
- ORD
2 stops18h 01m
American Airlines
Deal found 2/3![American Airlines logo]()
$578
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:30 am
STL
- SKB
2 stops32h 43m
United Airlines
Thu 4/309:50 am
SKB
- STL
2 stops13h 40m
United Airlines
Deal found 2/1![United Airlines logo]()
$1,349
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1211:00 am
MDW
- SKB
3 stops29h 45m
Multiple Airlines
Wed 4/154:20 pm
SKB
- MDW
3 stops24h 00m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$1,387
This American Airlines deal was found by Cheapflights users on 2/1. 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 6/245:00 am
ORD
- SKB
1 stop7h 30m
American Airlines
Tue 6/302:40 pm
SKB
- ORD
1 stop10h 44m
American Airlines
Deal found 2/1![American Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 pm
ORD
- SKB
1 stop17h 30m
American Airlines
Thu 5/212:40 pm
SKB
- ORD
1 stop8h 39m
American Airlines
Deal found 2/2![American Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 5/16:55 pm
STL
- SKB
1 stop17h 05m
American Airlines
Wed 5/62:32 pm
SKB
- STL
1 stop8h 52m
American Airlines
Deal found 2/3![American Airlines logo]()
$659
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:55 pm
STL
- SKB
2 stops17h 35m
American Airlines
Sat 5/22:32 pm
SKB
- STL
2 stops18h 58m
American Airlines
Deal found 2/2![American Airlines logo]()
$679
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:20 pm
STL
- SKB
1 stop18h 01m
American Airlines
Fri 4/102:32 pm
SKB
- STL
1 stop8h 52m
American Airlines
Deal found 2/2![American Airlines logo]()
$747
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:05 pm
STL
- SKB
3 stops20h 45m
Multiple Airlines
Fri 4/108:30 am
SKB
- STL
3 stops31h 54m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,554
Last-minute flights from Illinois to BasseterreDiscover last-minute flight deals from Illinois to Basseterre. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Basseterre. Data last updated February 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 3/36:59 pm
ORD
- SKB
1 stop17h 23m
American Airlines
Tue 3/102:24 pm
SKB
- ORD
1 stop9h 53m
American Airlines
Deal found 2/1![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 3/56:59 pm
ORD
- SKB
1 stop17h 23m
American Airlines
Thu 3/122:24 pm
SKB
- ORD
1 stop11h 14m
American Airlines
Deal found 2/3![American Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 2/1. 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.
Fri 3/67:59 pm
ORD
- SKB
1 stop17h 14m
Delta
Sat 3/141:50 pm
SKB
- ORD
1 stop11h 04m
Delta
Deal found 2/1![Delta logo]()
$603
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:59 pm
ORD
- SKB
1 stop17h 25m
American Airlines
Fri 3/132:24 pm
SKB
- ORD
1 stop11h 14m
American Airlines
Deal found 2/2![American Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 3/115:00 am
ORD
- SKB
1 stop7h 24m
American Airlines
Mon 3/162:24 pm
SKB
- ORD
1 stop11h 14m
American Airlines
Deal found 2/3![American Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 3/135:00 am
ORD
- SKB
1 stop7h 21m
American Airlines
Sat 3/214:30 pm
SKB
- ORD
1 stop17h 23m
American Airlines
Deal found 2/1![American Airlines logo]()
$637
One-way flights from Illinois to BasseterreSearch for one-way flight options from Illinois to Basseterre. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Illinois to Basseterre. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:56 pm
ORD
- SKB
1 stop20h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:13 pm
ORD
- SKB
2 stops15h 08m
American Airlines
Deal found 2/2![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:56 pm
MDW
- SKB
3 stops26h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 2/2. 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.
Sat 4/46:00 am
MDW
- SKB
1 stop7h 10m
Delta
Deal found 2/2![Delta logo]()
$473
Find flight deals from Illinois to Basseterre
Keep the following information in mind while searching for Illinois to Basseterre flight deals. Data was last updated February 4, 2026.
Round-trip from | $543 (American Airlines) |
|---|---|
One-way from | $287 (Kiwi.com) |
Popular in | August |
Cheapest in | July |
Average price | $705 |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Basseterre 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 February 4, 2026.
Use the filters below to find and compare flights from Illinois to Basseterre that are best for you.
Fly from
Illinois
Fly to
Basseterre
Route
Depart
Return
Price
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Tue 3/3
7:40 pm-2:22 pm
1 stop16h 42m
Basseterre Robert Bradshaw Intl
Tue 3/10
2:24 pm-11:17 pm
1 stop9h 53m
$543
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 4/4
6:59 pm-1:21 pm
1 stop17h 22m
Basseterre Robert Bradshaw Intl
Sat 4/11
4:50 pm-12:25 am
1 stop8h 35m
$573
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Thu 3/5
8:58 pm-2:22 pm
2 stops15h 24m
Basseterre Robert Bradshaw Intl
Thu 3/12
2:24 pm-7:25 am
2 stops18h 01m
$578
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Wed 6/24
5:00 am-1:30 pm
1 stop7h 30m
Basseterre Robert Bradshaw Intl
Tue 6/30
2:40 pm-12:24 am
1 stop10h 44m
$587
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 5/16
7:00 pm-1:30 pm
1 stop17h 30m
Basseterre Robert Bradshaw Intl
Thu 5/21
2:40 pm-10:19 pm
1 stop8h 39m
$587
ChicagoBasseterre
MDW - SKB
MDWSKB
Chicago Midway
Sat 4/18
6:00 am-2:10 pm
1 stop7h 10m
Basseterre Robert Bradshaw Intl
Sat 4/25
1:55 pm-10:28 pm
1 stop9h 33m
$603
St. LouisBasseterre
STL - SKB
STLSKB
Lambert-St Louis
Fri 5/1
6:55 pm-1:00 pm
1 stop17h 05m
Basseterre Robert Bradshaw Intl
Wed 5/6
2:32 pm-10:24 pm
1 stop8h 52m
$659
St. LouisBasseterre
STL - SKB
STLSKB
Lambert-St Louis
Mon 4/27
6:55 pm-1:30 pm
2 stops17h 35m
Basseterre Robert Bradshaw Intl
Sat 5/2
2:32 pm-8:30 am
2 stops18h 58m
$679
St. LouisBasseterre
STL - SKB
STLSKB
Lambert-St Louis
Sat 4/4
6:20 pm-1:21 pm
1 stop18h 01m
Basseterre Robert Bradshaw Intl
Fri 4/10
2:32 pm-10:24 pm
1 stop8h 52m
$747
St. LouisBasseterre
STL - SKB
STLSKB
Lambert-St Louis
Sun 4/26
6:30 am-4:13 pm
2 stops32h 43m
Basseterre Robert Bradshaw Intl
Thu 4/30
9:50 am-10:30 pm
2 stops13h 40m
$1,349
Showing 1-10 of 16 results
Best time to book a flight from Illinois to Basseterre
Have a flexible travel schedule? Discover the best time to fly to Basseterre from Illinois with our price prediction graph.
ORD-SKB
MDW-SKB
STL-SKB
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 Illinois to Basseterre
USIL-SKB
ORD-SKB
MDW-SKB
STL-SKB
What is the cheapest month to book a flight from Illinois to Basseterre?
Currently, May is the cheapest month in which you can book a flight from Illinois to Basseterre (average of $465). Flying from Illinois to Basseterre in March is currently the most expensive (average of $780). 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.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Basseterre. 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
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Alternative routes for Illinois to Basseterre
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Other flights to Basseterre
Explore flights to Basseterre departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 4, 2026.
Complete your trip
Complete your trip to Basseterre by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Illinois to Basseterre, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Basseterre flights
Browse other Illinois and Basseterre flight options. Last updated on February 4, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Illinois to Basseterre flights
Consider these flights traveling from Illinois to Basseterre.
Top airline flying from Illinois to Basseterre
Discover the top airline that operate flights from Illinois to Basseterre. 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$737 | FlexibilityNo cancel fee | On-time71% |