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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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap 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 October 14, 2025.

Round-trip from

$504
(American Airlines)

One-way from

$335
(American Airlines)

Popular in

August

Cheapest in

January
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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Highest demand for flights based on searches. 21% potential increase in price ($302 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($97 potential savings vs. average RT price).
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Find 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 October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/307:00 amORD - AXA
1 stop8h 01mAmerican Airlines
Sat 12/65:20 pmAXA - ORD
1 stop17h 29mAmerican Airlines
Deal found 10/12$504
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:00 amORD - AXA
1 stop7h 40mAmerican Airlines
Mon 12/85:20 pmAXA - ORD
1 stop9h 17mAmerican Airlines
Deal found 10/12$529
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:00 amORD - AXA
2 stops10h 01mAmerican Airlines
Mon 11/245:41 pmAXA - ORD
2 stops15h 23mAmerican Airlines
Deal found 10/12$569
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 pmORD - AXA
2 stops15h 46mAmerican Airlines
Sat 12/63:03 pmAXA - ORD
2 stops10h 48mAmerican Airlines
Deal found 10/12$616
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 12/105:00 amORD - AXA
2 stops9h 40mAmerican Airlines
Sun 12/145:20 pmAXA - ORD
1 stop17h 29mAmerican Airlines
Deal found 10/13$621
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sun 11/237:17 pmORD - AXA
1 stop19h 44mAmerican Airlines
Thu 11/273:11 pmAXA - ORD
1 stop11h 26mAmerican Airlines
Deal found 10/13$623
This American Airlines deal was found by Cheapflights users on 10/14. 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 12/115:00 amORD - AXA
1 stop9h 40mAmerican Airlines
Sun 12/145:20 pmAXA - ORD
1 stop17h 29mAmerican Airlines
Deal found 10/14$641
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:37 pmORD - AXA
2 stops19h 59mAmerican Airlines
Wed 12/315:30 pmAXA - ORD
2 stops18h 33mAmerican Airlines
Deal found 10/12$666

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 October 14, 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

Sun 12/7

7:00 am-4:40 pm

1 stop7h 40m

The Valley Wallblake Intl

Sat 12/13

3:03 pm-12:37 am

1 stop11h 34m

$504

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 2/21

7:09 pm-2:10 pm

1 stop17h 01m

The Valley Wallblake Intl

Wed 2/25

5:10 pm-11:59 pm

1 stop8h 49m

$573

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/25

7:01 am-4:25 pm

1 stop7h 24m

The Valley Wallblake Intl

Tue 3/3

5:10 pm-11:59 pm

1 stop8h 49m

$573

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 2/5

7:00 am-4:26 pm

1 stop7h 26m

The Valley Wallblake Intl

Tue 2/10

5:06 pm-9:05 am

1 stop17h 59m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 1/14

7:50 pm-2:23 pm

2 stops16h 33m

The Valley Wallblake Intl

Tue 1/20

5:06 pm-7:22 am

2 stops16h 16m

$628

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 12/11

5:00 am-4:40 pm

1 stop9h 40m

The Valley Wallblake Intl

Sun 12/14

5:20 pm-8:49 am

1 stop17h 29m

$641

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 11/18

5:00 am-2:31 pm

1 stop7h 31m

$335

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 11/18

6:40 am-1:30 pm

3 stops52h 50m

$343

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 11/7

3:26 pm-5:10 pm

2 stops23h 44m

$348

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 11/26

11:48 am-1:30 pm

3 stops23h 42m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 14 results
1
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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 October 14, 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
11,042 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 7h 40m. 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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Alternative routes for O'Hare Intl to Anguilla

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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$657Average$900FlexibilityNo cancel feeOn-time71%

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