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$681+ Cheap flights from O'Hare Intl (ORD) to Anguilla

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$702
(American Airlines)

Popular in

August

Cheapest in

December

Average price

$853
From Chicago O'Hare Intl to Anguilla
Search Deals
Highest demand for flights based on searches. 30% potential increase in price ($456 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($97 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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 3/246:58 pmORD - AXA
1 stop17h 07mAmerican Airlines
Fri 3/283:55 pmAXA - ORD
2 stops16h 17mAmerican Airlines
Deal found 2/19$681
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sun 3/97:42 pmORD - AXA
2 stops20h 53mMultiple Airlines
Fri 3/149:46 amAXA - ORD
3 stops25h 50mMultiple Airlines
Deal found 2/19$1,071
This United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:25 amORD - AXA
1 stop7h 30mUnited Airlines
Sun 11/309:35 amAXA - ORD
1 stop11h 17mUnited Airlines
Deal found 2/18$2,893

Find flights from O'Hare Intl to Anguilla within your budget

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 February 20, 2025.

Fly from

O'Hare Intl

Fly to

Anguilla

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 3/24

6:58 pm-1:05 pm

1 stop17h 07m

The Valley Wallblake Intl

Fri 3/28

3:55 pm-7:12 am

2 stops16h 17m

$681

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 3/9

7:42 pm-5:35 pm

2 stops20h 53m

The Valley Wallblake Intl

Fri 3/14

9:46 am-10:36 am

3 stops25h 50m

$1,071

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from O'Hare Intl to Anguilla

Get recent, data-driven insights about flights from O'Hare Intl to Anguilla including ideal travel times, pricing trends, and more.

Rainfall in Anguilla by month

Plan your trip to Anguilla by taking into account the average rainfall totals by month.

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.

Temperature in Anguilla by month

Plan your trip to Anguilla by taking into account the average temperature totals by month.

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).

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 20, 2025.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.3

Overall

7.2

Crew

8.0

Food

6.5

Boarding

7.5

Entertainment

7.0

Reviews

1 / 20

10.0
Excellent

Anonymous,Jan 2025

PIT - DFW

Due to gate changes,we nearly missed our flight. The gate agent reassigned our seats and would NOT give us our assigned seats,but she did honor that same request to the man who arrived after us. Her rudeness and difficulty was not appropriate.

American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.3

Overall

7.2

Crew

8.0

Food

6.5

Boarding

7.5

Entertainment

7.0

Reviews

1 / 20

10.0
Excellent

Anonymous,Jan 2025

PIT - DFW

Due to gate changes,we nearly missed our flight. The gate agent reassigned our seats and would NOT give us our assigned seats,but she did honor that same request to the man who arrived after us. Her rudeness and difficulty was not appropriate.

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?

    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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$614Average$781FlexibilityNo cancel feeOn-time71%
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