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Anguilla

$369+ Cheap flights from Chicago (CHI) 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 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Chicago to Anguilla

Keep the following information in mind while searching for Chicago to Anguilla flight deals. Data was last updated April 24, 2025.

Round-trip from

$677
(American Airlines)

One-way from

$369
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$765
From Chicago (CHI) to Anguilla
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One-way flight from Chicago (CHI) to Anguilla
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Highest demand for flights based on searches. 31% potential increase in price ($474 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($99 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Anguilla

Cheapest flights from Chicago to Anguilla
Explore the most affordable flight options available from Chicago to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 7/266:55 pmORD - AXA
1 stop17h 30mAmerican Airlines
Fri 8/12:05 pmAXA - ORD
1 stop10h 52mAmerican Airlines
Deal found 4/23$677
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:03 pmORD - AXA
2 stops22h 32mMultiple Airlines
Sat 2/219:46 amAXA - ORD
2 stops10h 47mMultiple Airlines
Deal found 4/23$1,820

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 April 24, 2025.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.

Fly from

Chicago

Fly to

Anguilla

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/26

6:55 pm-1:25 pm

1 stop17h 30m

The Valley Wallblake Intl

Fri 8/1

2:05 pm-11:57 pm

1 stop10h 52m

$677

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 5/7

6:03 pm-5:35 pm

2 stops22h 32m

The Valley Wallblake Intl

Sat 2/21

9:46 am-6:33 pm

2 stops10h 47m

$1,820

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 6/18

5:05 am-3:10 pm

2 stops33h 05m

$369

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 5/6

3:00 pm-3:02 pm

2 stops23h 02m

$482

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Tue 5/6

7:00 pm-3:40 pm

3 stops43h 40m

$558

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Best time to book a flight from Chicago to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Chicago 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 to Anguilla

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 April 24, 2025.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago to Anguilla that include hotel bookings?

    Yes. In addition to deals on Chicago to Anguilla flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Anguilla?

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

  • Can I find deals for business class flights from Chicago to Anguilla?

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to Anguilla

Discover the top airline that operate flights from Chicago 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$629Average$897FlexibilityNo cancel feeOn-time71%

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