$333+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Dec 13 — Dec 201
Round-trip
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 Chicago to Anguilla
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Best
Last-minute
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 November 13, 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 November 13, 2026.
This American Airlines deal was found by Cheapflights users on 11/8. 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 04m
Tue 12/153:34 pm -
1 stop11h 19m
Deal found 11/8![American Airlines logo]()
$687
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/35:00 am -
1 stop9h 59m
Mon 12/75:39 pm -
1 stop9h 14m
Deal found 11/13![American Airlines logo]()
$1,021
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Tue 12/84:00 pm -
3 stops23h 35m
Tue 12/159:00 am -
2 stops18h 08m
Deal found 11/9![Multiple Airlines logo]()
$1,273
This Mytrip deal was found by Cheapflights users on 11/12. 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 12/275:59 pm -
2 stops20h 31m
Sun 1/37:55 am -
3 stops30h 05m
Deal found 11/12![Multiple Airlines logo]()
$1,301
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 November 13, 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 November 13, 2026.
This American Airlines deal was found by Cheapflights users on 11/9. 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 04m
Tue 12/153:34 pm -
1 stop11h 19m
Deal found 11/9![American Airlines logo]()
$687
This American Airlines deal was found by Cheapflights users on 11/10. 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 1/317:00 am -
1 stop7h 55m
Sat 2/61:15 pm -
1 stop12h 44m
Deal found 11/10![American Airlines logo]()
$721
This American Airlines deal was found by Cheapflights users on 11/13. 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 1/295:00 am -
1 stop9h 55m
Thu 2/45:35 pm -
1 stop17h 55m
Deal found 11/13![American Airlines logo]()
$734
This American Airlines deal was found by Cheapflights users on 11/8. 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 2/245:14 am -
2 stops9h 07m
Sun 2/285:01 pm -
1 stop17h 09m
Deal found 11/8![American Airlines logo]()
$806
Last-minute flights from Chicago to AnguillaDiscover last-minute flight deals from Chicago to Anguilla. Data last updated November 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Anguilla. Data last updated November 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/35:00 am -
1 stop9h 59m
Mon 12/75:39 pm -
1 stop9h 14m
Deal found 11/13![American Airlines logo]()
$1,021
This American Airlines deal was found by Cheapflights users on 11/8. 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 04m
Tue 12/153:34 pm -
1 stop11h 19m
Deal found 11/8![American Airlines logo]()
$687
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Tue 12/84:00 pm -
3 stops23h 35m
Tue 12/159:00 am -
2 stops18h 08m
Deal found 11/9![Multiple Airlines logo]()
$1,273
This Mytrip deal was found by Cheapflights users on 11/12. 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 12/275:59 pm -
2 stops20h 31m
Sun 1/37:55 am -
3 stops30h 05m
Deal found 11/12![Multiple Airlines logo]()
$1,301
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 November 13, 2026.
Search for one-way flight options from Chicago to Anguilla. Find affordable one-way fares based on user searches. Data last updated November 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 1/101:30 pm -
2 stops25h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 1/128:10 am -
3 stops31h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 11/10. 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 1/115:00 am -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![American Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2111:53 pm -
3 stops36h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Multiple Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 11/10. 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 1/125:00 am -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![American Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2311:53 pm -
3 stops35h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Multiple Airlines logo]()
$452
This American Airlines deal was found by Cheapflights users on 11/10. 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 1/104:46 pm -
1 stop20h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![American Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 1/1110:31 pm -
3 stops33h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$618
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 November 13, 2026.
Round-trip from | $687 (American Airlines) |
|---|---|
One-way from | $333 (Kiwi.com) |
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 November 13, 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 1/11
5:00 am-4:55 pm
1 stop9h 55m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$364
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 1/12
5:00 am-4:55 pm
1 stop9h 55m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$449
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 11/23
11:53 pm-11:25 am
2 stops33h 32m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$541
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 11/23
7:50 pm-2:57 pm
1 stop17h 07m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$651
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
7:50 pm-2:54 pm
1 stop17h 04m
The Valley Wallblake Intl
Tue 12/15
3:34 pm-12:53 am
1 stop11h 19m
$687
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sun 1/31
7:00 am-4:55 pm
1 stop7h 55m
The Valley Wallblake Intl
Sat 2/6
1:15 pm-11:59 pm
1 stop12h 44m
$721
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Fri 1/29
5:00 am-4:55 pm
1 stop9h 55m
The Valley Wallblake Intl
Thu 2/4
5:35 pm-9:30 am
1 stop17h 55m
$734
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sun 11/22
7:50 pm-2:57 pm
1 stop17h 07m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$748
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Sun 1/10
10:31 pm-3:25 pm
3 stops14h 54m
The Valley Wallblake Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$793
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Wed 2/24
5:14 am-4:21 pm
2 stops9h 07m
The Valley Wallblake Intl
Sun 2/28
5:01 pm-8:10 am
1 stop17h 09m
$806
Showing 1-10 of 11 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 November 13, 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.
Crew
7.9
Overall
7.0
Comfort
7.1
Entertainment
6.8
Boarding
7.4
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Overall
7.0
Comfort
7.1
Entertainment
6.8
Boarding
7.4
Food
6.4
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 November 13, 2026.
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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 November 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$644 | Average$768 | FlexibilityNo cancel fee | On-time71% |