In terms of precipitation, rainfall in Anguilla ranges from 1.6 - 4.3 inches per month. August is typically the wettest month, when rainfall can reach 4.3 in. February is typically the driest time to visit Anguilla when rainfall is around 1.6 in.

If weather is an important factor for your trip to Anguilla, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 78.8 F).

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Anguilla?

Due to multiple factors, expect to potentially pay more when booking in August. For low rates, June can be a great choice for travel to Anguilla. Flights to Anguilla from Chicago O'Hare Intl Airport in June are about $1,044 on average during June, but can be found for as low as $657.

What is the cheapest time of day to fly from ORD to AI?

When flying from Chicago O'Hare Intl Airport to Anguilla, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

$335+ Cheap Flights from Chicago O'Hare Intl Airport to Anguilla

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Cheap flight deals from O'Hare Intl to Anguilla

Round-trip from	$602 (American Airlines)
One-way from	$335 (American Airlines)
Popular in	August
Cheapest in	June
Average price	$1,996

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. 27% potential increase in price ($387 potential increase over avg. RT price).

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Cheapest flight prices on average. 10% potential price decrease ($95 potential savings vs. average RT price).

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Average for round-trip flights in August 2025

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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 August 14, 2025.

Sat 11/18:54 pmORD - AXA

2 stops16h 24mAmerican Airlines

Sat 11/85:19 pmAXA - ORD

1 stop9h 02mAmerican Airlines

Deal found 8/12

$602

Wed 8/278:52 amORD - AXA

2 stops31h 23mMultiple Airlines

Mon 9/19:35 amAXA - ORD

2 stops35h 28mMultiple Airlines

Deal found 8/12

$1,753

Best flights from O'Hare Intl to Anguilla
Discover carefully curated flight deals from O'Hare Intl to Anguilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Sat 11/18:54 pmORD - AXA

2 stops16h 24mAmerican Airlines

Sat 11/85:19 pmAXA - ORD

1 stop9h 02mAmerican Airlines

Deal found 8/12

$602

Wed 8/278:52 amORD - AXA

2 stops31h 23mMultiple Airlines

Mon 9/19:35 amAXA - ORD

2 stops35h 28mMultiple Airlines

Deal found 8/12

$1,753

Fri 1/236:35 pmORD - AXA

2 stops16h 02mAmerican Airlines

Sun 2/13:25 pmAXA - ORD

1 stop11h 05mAmerican Airlines

Deal found 8/11

$2,350

Last-minute flights from O'Hare Intl to Anguilla
Discover last-minute flight deals from O'Hare Intl to Anguilla. Data last updated August 14, 2025 and is based on user searches.

Wed 8/278:52 amORD - AXA

2 stops31h 23mMultiple Airlines

Mon 9/19:35 amAXA - ORD

2 stops35h 28mMultiple Airlines

Deal found 8/12

$1,753

One-way flights from O'Hare Intl to Anguilla
Search for one-way flight options from O'Hare Intl to Anguilla. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Mon 12/15:00 amORD - AXA

1 stop9h 25mAmerican Airlines

Deal found 8/12

$335

Wed 12/35:05 amORD - AXA

2 stops10h 05mMultiple Airlines

Deal found 8/12

$368

Thu 12/45:59 pmORD - AXA

2 stops21h 11mMultiple Airlines

Deal found 8/12

$386

Sat 11/297:07 pmORD - AXA

1 stop17h 11mAmerican Airlines

Deal found 8/12

$390

Fri 11/284:00 pmORD - AXA

2 stops22h 25mAmerican Airlines

Deal found 8/12

$415

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/1

8:54 pm-2:18 pm

2 stops16h 24m

The Valley Wallblake Intl

Sat 11/8

5:19 pm-12:21 am

1 stop9h 02m

$602

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 8/27

8:52 am-5:15 pm

2 stops31h 23m

The Valley Wallblake Intl

Mon 9/1

9:35 am-8:03 pm

2 stops35h 28m

$1,753

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 1/23

6:35 pm-12:37 pm

2 stops16h 02m

The Valley Wallblake Intl

Sun 2/1

3:25 pm-12:30 am

1 stop11h 05m

$2,350

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 12/1

5:00 am-4:25 pm

1 stop9h 25m

$335

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 12/3

5:05 am-5:10 pm

2 stops10h 05m

$368

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 12/4

5:59 pm-5:10 pm

2 stops21h 11m

$386

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 12/3

5:00 am-4:15 pm

1 stop9h 15m

$390

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 11/30

7:00 am-4:25 pm

1 stop7h 25m

$390

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/29

6:35 pm-4:25 pm

2 stops19h 50m

$390

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 12/2

5:00 am-2:18 pm

1 stop7h 18m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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

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

10,000 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

American Airlines

7.2

Good

10,000 reviews

American Airlines

7.2

Good

10,000 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Related info for your journey

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.

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from O'Hare Intl to Anguilla

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$654	Average$899	FlexibilityNo cancel fee	On-time71%

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$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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from O'Hare Intl to Anguilla with Cheapflights

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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 August 14, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from O'Hare Intl to Anguilla

Cheapest flights from O'Hare Intl to AnguillaExplore 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 August 14, 2025.

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 August 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Anguilla that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Anguilla

Reviews of airlines servicing Anguilla

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.

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.

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Anguilla

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from O'Hare Intl to Anguilla

100% Free

Book with Flexibility

Travel Smart

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 August 14, 2025.