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Anguilla

$335+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
ene. 9 — ene. 161
vie. 1/9
vie. 1/16
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 diciembre 10, 2025.

This American Airlines deal was found by Cheapflights users on 12/8. 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.
vie. 12/127:07 pmORD - AXA
1 stop15h 33mAmerican Airlines
dom. 12/145:20 pmAXA - ORD
1 stop17h 29mAmerican Airlines
Deal found 12/8$590
This American Airlines deal was found by Cheapflights users on 12/8. 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.
lun. 12/297:26 pmORD - AXA
1 stop19h 10mAmerican Airlines
mar. 1/65:06 pmAXA - ORD
1 stop17h 59mAmerican Airlines
Deal found 12/8$651
This American Airlines deal was found by Cheapflights users on 12/8. 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.
mié. 12/175:00 amORD - AXA
1 stop9h 40mAmerican Airlines
vie. 12/265:30 pmAXA - ORD
1 stop17h 17mAmerican Airlines
Deal found 12/8$739
This American Airlines deal was found by Cheapflights users on 12/9. 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.
sáb. 12/208:35 pmORD - AXA
1 stop15h 38mAmerican Airlines
jue. 12/252:53 pmAXA - ORD
1 stop11h 00mAmerican Airlines
Deal found 12/9$764
This American Airlines deal was found by Cheapflights users on 12/8. 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.
mié. 12/175:00 amORD - AXA
1 stop9h 40mAmerican Airlines
dom. 12/282:53 pmAXA - ORD
1 stop11h 50mAmerican Airlines
Deal found 12/8$794
This American Airlines deal was found by Cheapflights users on 12/8. 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.
mié. 12/175:00 amORD - AXA
1 stop9h 40mAmerican Airlines
sáb. 12/272:53 pmAXA - ORD
2 stops11h 06mAmerican Airlines
Deal found 12/8$819
This American Airlines deal was found by Cheapflights users on 12/8. 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.
lun. 12/297:26 pmORD - AXA
1 stop19h 10mAmerican Airlines
lun. 1/55:30 pmAXA - ORD
1 stop17h 35mAmerican Airlines
Deal found 12/8$826

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 diciembre 10, 2025.

Round-trip from

$485
(American Airlines)

One-way from

$335
(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 diciembre 10, 2025.
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

sáb. 2/21

7:13 pm-2:19 pm

1 stop17h 06m

The Valley Wallblake Intl

jue. 2/26

5:24 pm-9:02 am

1 stop17h 38m

$485

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

sáb. 2/7

7:30 pm-2:23 pm

1 stop16h 53m

The Valley Wallblake Intl

mié. 2/11

5:06 pm-9:02 am

1 stop17h 56m

$485

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

vie. 1/30

7:30 pm-12:34 pm

1 stop15h 04m

The Valley Wallblake Intl

mié. 2/4

5:06 pm-9:05 am

1 stop17h 59m

$515

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

jue. 2/12

9:02 pm-2:19 pm

2 stops15h 17m

The Valley Wallblake Intl

mar. 2/17

5:24 pm-8:48 am

1 stop17h 24m

$570

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

jue. 5/14

5:00 am-3:05 pm

1 stop9h 05m

The Valley Wallblake Intl

lun. 5/18

4:05 pm-6:24 am

2 stops15h 19m

$628

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

lun. 12/29

7:26 pm-4:36 pm

1 stop19h 10m

The Valley Wallblake Intl

mar. 1/6

5:06 pm-9:05 am

1 stop17h 59m

$651

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

lun. 2/2

7:00 am-4:26 pm

1 stop7h 26m

$335

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

mié. 1/28

7:30 pm-4:26 pm

1 stop18h 56m

$382

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

lun. 2/2

5:40 am-3:40 pm

3 stops32h 00m

$414

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

mié. 1/28

10:48 am-3:50 pm

2 stops27h 02m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 diciembre 10, 2025.
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
11,048 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,048 reviews
American Airlines
7.2
Good
11,048 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 06m. 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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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 diciembre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$597Average$754FlexibilityNo cancel feeOn-time71%

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