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Anguilla

$345+ Cheap flights from O'Hare Intl (ORD) 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
2月 24 — 3月 31
週二 2/24
週二 3/3
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Anguilla

Cheapest flights from O'Hare Intl to Anguilla
Explore the most affordable flight options available from O'Hare Intl to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 1月 25, 2026.

This American Airlines deal was found by Cheapflights users on 1/24. 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.
週五 2/64:49 pm
ORD
-
AXA
1 stop17h 45m
American Airlines
週二 2/105:06 pm
AXA
-
ORD
1 stop17h 59m
American Airlines
Deal found 1/24$572
This American Airlines deal was found by Cheapflights users on 1/22. 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.
週日 2/226:01 am
ORD
-
AXA
1 stop8h 27m
American Airlines
週三 2/255:10 pm
AXA
-
ORD
1 stop17h 43m
American Airlines
Deal found 1/22$578
This American Airlines deal was found by Cheapflights users on 1/23. 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.
週日 2/85:00 am
ORD
-
AXA
1 stop7h 23m
American Airlines
週五 2/133:10 pm
AXA
-
ORD
1 stop10h 24m
American Airlines
Deal found 1/23$592
This American Airlines deal was found by Cheapflights users on 1/24. 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.
週三 8/125:00 am
ORD
-
AXA
1 stop7h 24m
American Airlines
週三 8/192:04 pm
AXA
-
ORD
1 stop10h 53m
American Airlines
Deal found 1/24$594
This American Airlines deal was found by Cheapflights users on 1/23. 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.
週六 4/116:58 pm
ORD
-
AXA
1 stop17h 17m
American Airlines
週六 4/184:57 pm
AXA
-
ORD
1 stop8h 30m
American Airlines
Deal found 1/23$619
This American Airlines deal was found by Cheapflights users on 1/24. 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.
週日 4/55:00 am
ORD
-
AXA
2 stops9h 29m
American Airlines
週日 4/124:57 pm
AXA
-
ORD
1 stop8h 30m
American Airlines
Deal found 1/24$629
This American Airlines deal was found by Cheapflights users on 1/23. 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.
週日 2/87:00 am
ORD
-
AXA
1 stop7h 26m
American Airlines
週六 2/145:10 pm
AXA
-
ORD
1 stop9h 27m
American Airlines
Deal found 1/23$633

Find flight deals from O'Hare Intl to Anguilla

Keep the following information in mind while searching for O'Hare Intl to Anguilla flight deals. Data was last updated 1月 25, 2026.

Round-trip from

$572
(American Airlines)

One-way from

$345
(American Airlines)
From Chicago O'Hare Intl to Anguilla
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One-way flight from Chicago O'Hare Intl to Anguilla
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 1月 25, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Anguilla that are best for you.

Fly from

O'Hare Intl

Fly to

Anguilla

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週五 2/6

4:49 pm-12:34 pm

1 stop17h 45m

The Valley Wallblake Intl

週二 2/10

5:06 pm-9:05 am

1 stop17h 59m

$572

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週日 2/22

6:01 am-4:28 pm

1 stop8h 27m

The Valley Wallblake Intl

週三 2/25

5:10 pm-8:53 am

1 stop17h 43m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週二 2/24

5:00 am-4:28 pm

1 stop9h 28m

The Valley Wallblake Intl

週二 3/3

5:10 pm-12:37 am

1 stop9h 27m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週六 4/11

6:58 pm-1:15 pm

1 stop17h 17m

The Valley Wallblake Intl

週六 4/18

4:57 pm-12:27 am

1 stop8h 30m

$619

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週一 4/6

6:59 pm-1:15 pm

1 stop17h 16m

$345

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

週日 3/29

5:28 pm-3:29 pm

1 stop21h 01m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Best time to book a flight from O'Hare Intl to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from O'Hare Intl with our price prediction graph.
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 Anguilla
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 1月 25, 2026.
See what other customers who have flown with American Airlines from Chicago O'Hare Intl Airport to Anguilla have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Anguilla?

    American Airlines can get you from Chicago O'Hare Intl Airport to Anguilla in just under 17h 45m. Your travel time can differ by up to . Airlines will cover a distance of 2197 mi.

  • Can I find deals for flights from O'Hare Intl to Anguilla that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Anguilla flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Anguilla?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Anguilla.

  • Can I find deals for business class flights from O'Hare Intl to Anguilla?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Anguilla by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from O'Hare Intl to Anguilla

Discover the top airline that operate flights from O'Hare Intl 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 1月 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$597Average$737FlexibilityNo cancel feeOn-time71%

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