$344+ Cheap flights from Chicago (CHI) to Anguilla
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Anguilla 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 Chicago to Anguilla
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One-way
Cheapest flights from Chicago to AnguillaExplore the most affordable flight options available from Chicago to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from Chicago to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:00 am -
1 stop10h 05m
Tue 11/105:45 pm -
1 stop16h 15m
Deal found 9/22![American Airlines logo]()
$637
This American Airlines deal was found by Cheapflights users on 9/19. 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 12/87:50 pm -
1 stop17h 07m
Tue 12/153:37 pm -
1 stop11h 07m
Deal found 9/19![American Airlines logo]()
$646
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:05 pm -
1 stop21h 00m
Sun 11/155:45 pm -
1 stop8h 59m
Deal found 9/20![American Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 9/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:06 pm -
2 stops15h 51m
Mon 12/75:45 pm -
2 stops17h 15m
Deal found 9/21![American Airlines logo]()
$745
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop9h 05m
Sun 11/155:45 pm -
2 stops15h 41m
Deal found 9/22![American Airlines logo]()
$750
Best flights from Chicago to AnguillaDiscover carefully curated flight deals from Chicago to Anguilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Chicago to Anguilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:00 am -
1 stop10h 05m
Tue 11/105:45 pm -
1 stop16h 15m
Deal found 9/22![American Airlines logo]()
$637
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:50 pm -
1 stop17h 07m
Tue 12/153:37 pm -
1 stop11h 07m
Deal found 9/22![American Airlines logo]()
$646
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:50 pm -
1 stop19h 15m
Sun 11/155:45 pm -
2 stops15h 41m
Deal found 9/20![American Airlines logo]()
$717
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:00 am -
1 stop7h 55m
Fri 1/155:35 pm -
2 stops15h 24m
Deal found 9/20![American Airlines logo]()
$745
This American Airlines deal was found by Cheapflights users on 9/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:06 pm -
2 stops15h 51m
Mon 12/75:45 pm -
2 stops17h 15m
Deal found 9/21![American Airlines logo]()
$745
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/186:00 am -
1 stop8h 55m
Tue 1/265:35 pm -
1 stop17h 55m
Deal found 9/23![American Airlines logo]()
$766
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/187:00 am -
1 stop7h 55m
Mon 1/255:35 pm -
1 stop9h 30m
Deal found 9/23![American Airlines logo]()
$813
This American Airlines deal was found by Cheapflights users on 9/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/148:55 pm -
2 stops15h 28m
Sat 3/204:18 pm -
1 stop18h 10m
Deal found 9/21![American Airlines logo]()
$1,215
Last-minute flights from Chicago to AnguillaDiscover last-minute flight deals from Chicago to Anguilla. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Anguilla. Data last updated September 24, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:35 am -
3 stops31h 05m
Sat 9/2612:30 pm -
2 stops25h 53m
Deal found 9/20![Multiple Airlines logo]()
$1,021
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:29 pm -
1 stop17h 46m
Wed 10/212:55 pm -
1 stop17h 52m
Deal found 9/20![American Airlines logo]()
$935
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:05 am -
1 stop8h 10m
Wed 10/212:55 pm -
1 stop10h 43m
Deal found 9/20![American Airlines logo]()
$974
This United deal was found by Cheapflights users on 9/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:55 am -
2 stops31h 40m
Tue 10/209:46 am -
2 stops35h 19m
Deal found 9/20![Multiple Airlines logo]()
$1,750
This United deal was found by Cheapflights users on 9/22. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 am -
2 stops31h 40m
Mon 10/269:46 am -
2 stops12h 44m
Deal found 9/22![Multiple Airlines logo]()
$1,579
One-way flights from Chicago to AnguillaSearch for one-way flight options from Chicago to Anguilla. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Chicago to Anguilla. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:20 pm -
3 stops42h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/106:00 am -
1 stop8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/106:00 am -
3 stops31h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$541
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/138:55 pm -
2 stops15h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$547
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:00 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$814
Find flight deals from Chicago to Anguilla
Keep the following information in mind while searching for Chicago to Anguilla flight deals. Data was last updated September 24, 2026.
Round-trip from | $637 (American Airlines) |
|---|---|
One-way from | $344 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 11/9
6:00 am-5:05 pm
1 stop9h 05m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$344
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Wed 2/10
6:00 am-4:55 pm
1 stop8h 55m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$457
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sat 2/13
6:20 pm-2:25 pm
3 stops42h 05m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$571
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sat 2/13
5:28 pm-4:46 pm
1 stop21h 18m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$571
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 11/9
2:16 pm-5:35 pm
2 stops25h 19m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$630
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 11/2
5:00 am-5:05 pm
1 stop10h 05m
The Valley Wallblake Intl
Tue 11/10
5:45 pm-8:00 am
1 stop16h 15m
$637
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
7:50 pm-2:57 pm
1 stop17h 07m
The Valley Wallblake Intl
Tue 12/15
3:37 pm-12:44 am
1 stop11h 07m
$646
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sun 11/8
7:50 pm-5:05 pm
1 stop19h 15m
The Valley Wallblake Intl
Sun 11/15
5:45 pm-7:26 am
2 stops15h 41m
$717
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Fri 1/8
7:00 am-4:55 pm
1 stop7h 55m
The Valley Wallblake Intl
Fri 1/15
5:35 pm-6:59 am
2 stops15h 24m
$745
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Thu 12/3
9:06 pm-2:57 pm
2 stops15h 51m
The Valley Wallblake Intl
Mon 12/7
5:45 pm-9:00 am
2 stops17h 15m
$745
Showing 1-10 of 14 resultsSorted by cheapest first
Best time to book a flight from Chicago to Anguilla
Have a flexible travel schedule? Discover the best time to fly to Anguilla from Chicago with our price prediction graph.
ORD-AXA
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 to Anguilla
CHI-AI0
ORD-AXA
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Anguilla
Get insights into the airlines that provide service to Anguilla. 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 Anguilla. Reviews last updated September 24, 2026.
Read through reviews of airlines operating flights from Chicago to Anguilla, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Entertainment
6.8
Food
6.4
Overall
7.0
Boarding
7.4
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Entertainment
6.8
Food
6.4
Overall
7.0
Boarding
7.4
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Anguilla. 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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Chicago and Anguilla flights
Browse other Chicago and Anguilla flight options. Last updated on September 24, 2026.
Popular flight searches
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Top airline flying from Chicago to Anguilla
Discover the top airline that operate flights from Chicago to Anguilla. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$529 | Average$768 | FlexibilityNo cancel fee | On-time71% |