$282+ Cheap flights from Chicago (CHI) to Anguilla
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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
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 Chicago to Anguilla
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Best
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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 February 4, 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 February 4, 2026.
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 11/147:07 pm
ORD
- AXA
1 stop17h 11m
American Airlines
Thu 11/192:58 pm
AXA
- ORD
1 stop11h 23m
American Airlines
Deal found 2/2![American Airlines logo]()
$594
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 5/177:00 pm
ORD
- AXA
1 stop17h 15m
American Airlines
Sun 5/244:41 pm
AXA
- ORD
1 stop17h 38m
American Airlines
Deal found 2/2![American Airlines logo]()
$601
This American Airlines deal was found by Cheapflights users on 1/31. 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 2/226:59 pm
ORD
- AXA
1 stop17h 31m
American Airlines
Wed 2/255:10 pm
AXA
- ORD
1 stop17h 43m
American Airlines
Deal found 1/31![American Airlines logo]()
$608
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 4/117:00 pm
ORD
- AXA
1 stop17h 15m
American Airlines
Sat 4/184:57 pm
AXA
- ORD
1 stop8h 28m
American Airlines
Deal found 2/1![American Airlines logo]()
$619
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 4/55:00 am
ORD
- AXA
2 stops9h 29m
American Airlines
Sun 4/124:57 pm
AXA
- ORD
1 stop8h 28m
American Airlines
Deal found 2/2![American Airlines logo]()
$629
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.
Mon 5/255:45 pm
ORD
- AXA
1 stop21h 16m
American Airlines
Mon 6/14:41 pm
AXA
- ORD
1 stop17h 38m
American Airlines
Deal found 2/4![American Airlines logo]()
$633
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 February 4, 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 February 4, 2026.
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 5/177:00 pm
ORD
- AXA
1 stop17h 15m
American Airlines
Sun 5/244:41 pm
AXA
- ORD
1 stop17h 38m
American Airlines
Deal found 2/2![American Airlines logo]()
$601
This American Airlines deal was found by Cheapflights users on 1/31. 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 2/226:59 pm
ORD
- AXA
1 stop17h 31m
American Airlines
Wed 2/255:10 pm
AXA
- ORD
1 stop17h 43m
American Airlines
Deal found 1/31![American Airlines logo]()
$608
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.
Mon 5/255:45 pm
ORD
- AXA
1 stop21h 16m
American Airlines
Wed 6/31:54 pm
AXA
- ORD
1 stop8h 19m
American Airlines
Deal found 2/4![American Airlines logo]()
$608
This American Airlines deal was found by Cheapflights users on 1/31. 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 6/65:45 pm
ORD
- AXA
1 stop21h 16m
American Airlines
Thu 6/114:41 pm
AXA
- ORD
1 stop17h 38m
American Airlines
Deal found 1/31![American Airlines logo]()
$608
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 4/117:00 pm
ORD
- AXA
1 stop17h 15m
American Airlines
Sat 4/184:57 pm
AXA
- ORD
1 stop8h 28m
American Airlines
Deal found 2/1![American Airlines logo]()
$619
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 4/57:00 am
ORD
- AXA
1 stop7h 29m
American Airlines
Sun 4/124:57 pm
AXA
- ORD
1 stop8h 28m
American Airlines
Deal found 2/2![American Airlines logo]()
$624
Last-minute flights from Chicago to AnguillaDiscover last-minute flight deals from Chicago to Anguilla. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Anguilla. Data last updated February 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 1/31. 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 2/226:59 pm
ORD
- AXA
1 stop17h 31m
American Airlines
Wed 2/255:10 pm
AXA
- ORD
1 stop17h 43m
American Airlines
Deal found 1/31![American Airlines logo]()
$608
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 3/15:00 am
ORD
- AXA
2 stops9h 28m
American Airlines
Sat 3/75:10 pm
AXA
- ORD
1 stop18h 44m
American Airlines
Deal found 2/2![American Airlines logo]()
$714
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 3/35:00 am
ORD
- AXA
1 stop7h 30m
American Airlines
Tue 3/104:09 pm
AXA
- ORD
1 stop9h 29m
American Airlines
Deal found 2/1![American Airlines logo]()
$654
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 3/46:59 pm
ORD
- AXA
1 stop17h 31m
American Airlines
Wed 3/114:09 pm
AXA
- ORD
1 stop9h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$679
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.
Sat 3/75:15 am
ORD
- AXA
2 stops9h 55m
Multiple Airlines
Sat 3/148:30 am
AXA
- ORD
3 stops26h 50m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$689
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 3/256:00 am
ORD
- AXA
1 stop8h 29m
American Airlines
Tue 4/74:57 pm
AXA
- ORD
1 stop8h 28m
American Airlines
Deal found 2/3![American Airlines logo]()
$704
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.
Mon 3/308:58 pm
ORD
- AXA
2 stops15h 33m
American Airlines
Tue 4/74:57 pm
AXA
- ORD
2 stops22h 16m
American Airlines
Deal found 2/3![American Airlines logo]()
$709
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.
Mon 3/306:59 pm
ORD
- AXA
1 stop17h 32m
American Airlines
Wed 4/14:09 pm
AXA
- ORD
2 stops23h 59m
American Airlines
Deal found 2/3![American Airlines logo]()
$732
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 February 4, 2026.
Search for one-way flight options from Chicago to Anguilla. 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 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:15 am
ORD
- AXA
2 stops30h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$282
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:29 pm
ORD
- AXA
3 stops22h 41m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$283
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.
Mon 4/67:00 am
ORD
- AXA
1 stop7h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$345
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/125:05 am
ORD
- AXA
3 stops34h 05m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$388
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 3/295:00 am
ORD
- AXA
2 stops9h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$445
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 2/118:56 pm
ORD
- AXA
2 stops15h 34m
American Airlines
Deal found 2/1![American Airlines logo]()
$476
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/105:15 am
ORD
- AXA
3 stops30h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$490
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 2/107:00 am
ORD
- AXA
1 stop7h 26m
American Airlines
Deal found 2/1![American Airlines logo]()
$500
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 February 4, 2026.
Round-trip from | $601 (American Airlines) |
|---|---|
One-way from | $345 (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 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.
Fly from
Chicago
Fly to
Anguilla
Route
Depart
Return
Price
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sun 5/17
7:00 pm-1:15 pm
1 stop17h 15m
The Valley Wallblake Intl
Sun 5/24
4:41 pm-9:19 am
1 stop17h 38m
$601
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sun 2/22
6:59 pm-2:30 pm
1 stop17h 31m
The Valley Wallblake Intl
Wed 2/25
5:10 pm-8:53 am
1 stop17h 43m
$608
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Mon 5/25
5:45 pm-4:01 pm
1 stop21h 16m
The Valley Wallblake Intl
Wed 6/3
1:54 pm-9:13 pm
1 stop8h 19m
$608
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sat 6/6
5:45 pm-4:01 pm
1 stop21h 16m
The Valley Wallblake Intl
Thu 6/11
4:41 pm-9:19 am
1 stop17h 38m
$608
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sat 4/11
7:00 pm-1:15 pm
1 stop17h 15m
The Valley Wallblake Intl
Sat 4/18
4:57 pm-12:25 am
1 stop8h 28m
$619
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sun 4/5
7:00 am-3:29 pm
1 stop7h 29m
The Valley Wallblake Intl
Sun 4/12
4:57 pm-12:25 am
1 stop8h 28m
$624
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Mon 2/9
5:15 am-1:30 pm
2 stops30h 15m
$282
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sat 2/14
4:43 pm-5:10 pm
2 stops22h 27m
$317
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Mon 4/6
7:00 am-3:29 pm
1 stop7h 29m
$345
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Sun 3/29
5:00 am-3:29 pm
2 stops9h 29m
$445
Showing 1-10 of 11 results
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 February 4, 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.
Entertainment
6.9
Comfort
7.2
Boarding
7.5
Food
6.4
Overall
7.2
Crew
8.0
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
Entertainment
6.9
Comfort
7.2
Boarding
7.5
Food
6.4
Overall
7.2
Crew
8.0
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
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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Alternative routes for Chicago to Anguilla
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Complete your trip
Complete your trip to Anguilla by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chicago to Anguilla, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Anguilla flights
Browse other Chicago and Anguilla flight options. Last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$597 | Average$731 | FlexibilityNo cancel fee | On-time71% |